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Background: Spent coffee grounds (SCG) are the most abundant waste byproducts generated from coffee beverage production worldwide. Typically, these grounds are seen as waste and end up in landfills. However, SCG contain valuable compounds that can be valorized and used in different applications. Notably, they are rich in carbohydrates, primarily galactomannan, arabinogalactan type II, and cellulose. Within the framework of a circular bioeconomy, the targeted degradation of these polysaccharides via a tailored cocktail of carbohydrate-active enzymes offers a promising strategy for producing high-value saccharides from coffee waste. Results: In this study, various mild pretreatments were evaluated to increase the enzyme accessibility of SCG-derived biomass, reduce lignin content, and minimize hemicellulose loss. Thermostable enzymes were selected to construct an enzymatic cocktail specifically targeting cellulose and hemicelluloses in pretreated SCGs. The approach used achieved a conversion of 52% of the polysaccharide content to oligo- and monosaccharides, producing 17.4 mg of reducing sugars and 5.1 mg of monosaccharides from 50 mg of SCG. Additionally, microwave pretreatment followed by the application of a thermostable endo β-mannanase resulted in the production of 62.3 mg of mannooligosaccharides from 500 mg of SCG. In vitro experiments demonstrated that the produced mannooligosaccharides exhibited prebiotic activity, promoting the growth and biofilm formation of five probiotic bacterial strains. Conclusions: This study highlights an effective strategy for the valorization of SCG polysaccharides through mild pretreatment and customized enzymatic cocktails in a circular bioeconomic context. The production of both monosaccharides and oligosaccharides with prebiotic activity illustrates the versatility and commercial potential of SCG as a substrate for high-value saccharides. Furthermore, the use of mild pretreatment methods and thermostable enzymes minimizes chemical inputs and energy demands, aligning with sustainable processing practices. The ability to selectively target and degrade specific polysaccharides within SCG not only enhances the yield of desirable products, but also preserves key structural components, reducing waste and promoting resource efficiency. [ABSTRACT FROM AUTHOR]

A water-soluble arene ruthenium metalla-rectangle (MR1) functionalized with boronic acid groups was used to host various fluorescent dyes (fluorescein, eosin Y, and erythrosin B). These simple host–guest systems partially quench the natural fluorescence of the dyes, which can be regained in the presence of saccharides, phosphorylated molecules, and other analytes. The intensity of the regained fluorescence is directly linked to the nature of the analyte, and it shows some dose–response relationships with saccharides and phosphorylated molecules that are not compatible with a displacement assay, thus suggesting an allosteric mechanism. Interestingly, when fluorescein is trapped by the metalla-rectangle in the presence of D-fructose, half of the maximum fluorescence intensity is recovered at a fructose concentration of 17.2 ± 4.7 μM, while, for D-glucose, a concentration of 50.6 ± 2.5 μM is required for the same effect. Indeed, all combinations of analyte–host–dye (seven analytes, one host, three dyes) show a unique dose–response relationship in water at pH 8.0. However, in the presence of naphthalene and pyrene, fluorescein⸦MR1 shows a different behavior, acting as an indicator displacement assay with the full recovery of fluorescence. All data were analyzed by unsupervised machine learning technologies (PCA and cluster analysis), suggesting that such systems with multiple analyte–response behaviors are offering new perspectives for the development of highly sensitive, easily tunable, water-soluble, fluorescent-based sensing arrays for biomolecules and other analytes. [ABSTRACT FROM AUTHOR]

The selective functionalization of carbohydrates holds a central position in synthetic carbohydrate chemistry, driving the ongoing quest for ideal approaches to manipulate these compounds. In this study, we introduce a general strategy that enables the regiodivergent functionalization of saccharides. The use of electron‐deficient photoactive 4‐tetrafluoropyridinylthio (SPyf) fragment as an adaptable activating group, facilitated efficient functionalization across all saccharide sites. More importantly, this activating group can be directly installed at the C1, C5 and C6 positions of biomass‐derived carbohydrates in a single step and in a site‐selective manner, allowing for the efficient and precision‐oriented modification of unprotected saccharides and glycans. [ABSTRACT FROM AUTHOR]

ABSTRACT Malting quality of barley is a complex characteristic, which is influenced by a combination of interacting traits that are regulated by various genetic and environmental factors. The activities of various enzymes play pivotal roles in determining the malting quality, as they drive the biochemical processes responsible for converting barley saccharides and proteins into fermentable sugars and amino acids during the malting process. In this study, 14 malting barley cultivars were used to investigate the relationship between enzyme activities and malting quality traits. The results revealed a significant correlation between α‐amylase activity and malt extract (MEX), viscosity (VIS), free α‐amino nitrogen (FAN), and Kolbach index (KI). In contrast, β‐amylase activity exhibited a significant correlation solely with diastatic power (DP). β‐glucanase activity was significantly correlated with FAN and KI. The elevated expression levels of both HvBmy1 and HvBmy2 contributed to high DP, and the activation of α‐amylase genes (HvAmy1 and HvAmy2) and β‐glucanase genes (HvGlb1 and HvGlb2) played a crucial role in producing high FAN and KI. These results enhance our understanding of the relations between enzyme activity and malting quality traits and thereby may facilitate further breeding for malt barley cultivars. [ABSTRACT FROM AUTHOR]

Conversion of hemicellulose streams and the constituent monosaccharides, xylose, arabinose, glucose, mannose, and galactose, was conducted to produce value‐added chemicals, including furfural, hydroxymethylfurfural (HMF), levulinic acid and anhydrosugars. The study aimed at developing a kinetic model relevant for direct post‐Organosolv hemicellulose conversion. Monosaccharides served as a tool to in detail describe the kinetic behavior and segregate contribution of hydrothermal decomposition and acid catalyzed dehydration at the temperature range of 120–190 °C. Catalyst free aqueous media demonstrated enhanced formation of furanics, while elevated temperatures led to significant saccharide isomerization. The introduction of sulfuric and formic acids maximized furfural yield and significantly reduced HMF concentration by facilitating its rehydration into levulinic acid (46 mol%). Formic acid additionally substantially enhanced formation of anhydrosaccharides. An excellent correlation between modeled and experimental data enabled process optimization to maximize furanic yield in two distinct hemicellulose streams. Sulfuric acid‐containing hemicellulose stream achieved the highest furfural yield after 30 minutes at 238 °C, primarily due to the high Ea for pentose dehydration (150–160 kJ mol−1). Contrarily, formic acid‐containing hemicellulose stream enabled maximal furfural yield at more moderate temperature and extended reaction time due to its lower Ea for the same reaction step (115–125 kJ mol−1). [ABSTRACT FROM AUTHOR]

At present, most synthetic graphite materials commonly used as anode active ingredients in lithium‐ion cells are produced by graphitization of petroleum cokes. The carbon footprint associated with synthetic graphite production is significant. Thus, bio‐derived and cheap precursors, such as saccharides, would be an attractive alternative for the sustainable production of graphitic carbons. However, they are non‐graphitizing at temperatures as high as 3000 °C, preserving the curved, fullerene‐like structure of graphene layers and microporosity. Consequently, many lithium ions are consumed during the formation of solid electrolyte interphase films and passivated in the nanovoids. Here, a method for the production of pure, crystalline, graphitic materials based on sucrose disposed of microporosity is presented, which also works with a variety of saccharides and other organic precursors of hard carbons—generally considered incapable of such transformation. This process employs catalytic graphitization by Si particles at high temperatures. The electrochemical response of such derived sucrose‐based graphite in Li‐ion half‐cells demonstrated its feasibility to serve as an anode active material for rechargeable Li‐ion batteries. [ABSTRACT FROM AUTHOR]

Simple Summary: The purpose of this study was to investigate the saccharides profile in muskrat scented glands in different secretion seasons. The significant changes in the metabolic pathways of nine saccharide substances in the scented gland were detected. The regulatory changes in saccharides metabolism in the scented gland ensure its metabolism and energy requirements during the secretion season. These results will help elucidate the regulatory mechanism of the gland during the musk secretion season. The adult male muskrat has a pair of scented glands, which show clear seasonal changes in their developmental status between the secretion season and non-secretion season. During the secretion season, the scented glands are much larger than in the non-secretion season, with the metabolism of glandular cells increasing and a large amount of musk being produced. In this work, the blood, musk, and scented gland tissue were collected from three healthy adult male muskrats during secretion season (September). And the blood and scented gland tissue from another three healthy adult male muskrats during the non-secretion season (November) were also sampled. The saccharides from blood and musk were detected by liquid chromatography–mass spectrometry (LC-MS), indicating the saccharides are concentrated in the scented glands during the secretion season. What is more, transcriptome analysis was employed to investigate the expression patterns of saccharides' pathways, suggesting some saccharides' metabolism-related genes undergo significant seasonal changes. Above all, scented gland saccharides' metabolism displays seasonal differences, and the enhancement in saccharides' metabolic activity during the secretion phase maintains glandular proliferation and secretion function. [ABSTRACT FROM AUTHOR]

Carbohydrates constitute the largest source of biomass on Earth, but their synthetic modification is challenging due to their high content in oxygen functionalities. The site‐ and stereoselective modification of native sugars is a definite goal of glycochemistry research. Recent efforts to bypass the need for protecting groups, leveraging selective activation through photochemical mechanisms for site‐selective C−C bond formation from native sugars, are likely to largely impact all glycochemistry‐related areas. Davis, Koh, and co‐workers have recently presented their use of photocatalysis to develop a "cap and glycosylate" approach for the site‐ and stereoselective C‐glycosylation of native sugars. A modernized direct radical functionalization of in situ formed thioglycoside using photocatalysis was used in the synthetic manipulation of unprotected carbohydrates. This allowed reaching complex saccharides, and post‐translational modification of proteins. [ABSTRACT FROM AUTHOR]

We developed a pyridine–acetylene–phenol macrocycle in which a fluorine atom was introduced in place of a hydroxy group, as a host for the selective binding to epimers of glucose. The fluorine atom was expected to work as a negatively charged infill repelling oxygen atoms of saccharides and prevent the efficient formation of a hydrogen‐bond network with a glucoside, whose cross‐section size is larger than those of the corresponding epimers, especially of a mannoside. UV–Vis and fluorescence titration experiments revealed that this host showed a higher affinity for a mannoside than a glucoside. 1H NMR and molecular modeling suggested that the fluorine atom acts as a moderate infill weakening the binding to a glucoside. This result indicates that selectivity for guest molecules can be modified by replacing a hydroxy group and a hydrogen atom in host molecules with a fluorine atom. [ABSTRACT FROM AUTHOR]

Brewer's spent grains (BSG) are a by-product of the beer industry and can be used to produce biofuels. In this case, the objective of this study was to obtain reducing sugars from this biomass by subcritical water hydrolysis in a semi-continuous mode after steam explosion. Temperatures of 120–180 °C, reaction times of 1–5 min, and pressures of 15–25 MPa were used for the steam explosion without CO2. Moistures of 10–50% (w/v), temperatures of 120–180 °C, reaction times of 1–5 min, and pressures of 15–25 MPa were used for the steam explosion with CO2. Subcritical water hydrolysis of solid-exploded material was developed at 210 °C, 15 MPa, a solid/feed ratio of 16 g/g, and a flow rate of 20 mL/min. The characterization of BSG, reducing sugar yields, kinetic profiles, the composition of monosaccharides and furanic moieties, and the characterization of remaining solid by Fourier transform infrared (FTIR) spectroscopy and scanning electron microscopy (SEM) were performed. For steam explosion with CO2, the significant variables were the temperature and moisture, and the optimized conditions were moisture of 50% (w/v), 120 °C, pretreatment for 1 min, and 15 MPa, with a reducing sugars yield of 18.41 ± 1.02 g/100 g BSG. For steam explosion without CO2, the significant variables were the time and temperature, and the optimized conditions were 120 °C, pretreatment for 1 min, and 15 MPa, with a reducing sugars yield of 17.05 ± 0.48 g/100 g BSG. The process was successful because the steam explosion ruptured the lignocellulosic matrix, and the subsequent process of subcritical water hydrolysis could dissociate the polymers into low-chain saccharides. [ABSTRACT FROM AUTHOR]

In this study, the taste quality difference between high (Ninghong-Jinhao tea, JH, unfolded fresh leaves) and low (Ninghong-Congou tea, CG, unfurled fresh leaves) grades of Ninghong tea (unique black tea) was analyzed from the perspective of sensory omics, non-targeted metabolomics, and chemical dose. JH was characterized by sweetness and mellowness with umami, while CG was characterized by sweetness and thickness. A total of 94 differential metabolites contribute to the quality difference between two grades. Further quantitative analysis revealed that JH exhibited a high accumulation of amino acids, catechins, and theaflavins, while CG demonstrated a high accumulation of water extract, tea polyphenols, flavonol glycosides, and saccharides. Taste activity values (TAVs) analysis revealed that the key taste components of JH and CG were catechin, epigallocatechin gallate, three theaflavins, caffeine, myrictin-3-O-glucoside, quercetin-3-O-rutinoside, quercetin-3-O-glucoside, quercetin-3-O-galactoside, kaempferol-3-O-rutinoside, kaempferol-3-O-glucoside, and gallic acid. Among the identified compounds, the TAVs of five flavonol glycosides in Ninghong tea were found to be greater than 10 for the first time. This study is helpful to understand the taste quality difference between different grades of Ninghong tea from the molecular sensory level, providing a scientific foundation for quality improvement and targeted regulation. [ABSTRACT FROM AUTHOR]

During the production of Wuyi rock tea, withering and fermentation play a crucial role in the primary processing of the tea, greatly influencing the development of its distinct taste characteristics. In this study, Rougui (Camellia sinensis) was selected as the research object to investigate the effects of withering and fermentation on metabolites and taste characteristics in tea leaves. The findings revealed that a total of 1249 metabolites were detected in Rougui leaves at various processing stages, of which only 40 key metabolites were significantly altered. The process of withering and fermentation is crucial to increase the content of organic acids, plumerane, alkaloids, nucleotides and derivatives, amino acids and derivatives, and free fatty acids in the leaves of Rougui and to decrease the content of saccharides, phenolic acids, flavonols, flavones, and flavanols, which in turn enhances the mellowness, fresh and brisk taste, and aroma of tea and attenuates the saccharides, bitterness, and astringency. Withering and fermentation had the greatest effect on the bitterness and astringency of Rougui taste characteristics, followed by mellowness. It can be seen that withering and fermentation were extremely important for the development of Rougui's special taste characteristics. The present study provides important support for optimizing Rougui processing and the formation of its special taste characteristics. [ABSTRACT FROM AUTHOR]

To date, humans are looking for suitable energy sources to meet the global demand for fuels. Among many candidates, biohydrogen (bio‐H2), a future fuel perspective, is expected to grow critically and receive considerable attention to replace fossil fuels. This review focuses on biohydrogen production via post‐method photocatalytic reforming of ideal feedstock and abundant lignocellulosic biomass. Renewable biomass precursors are used without net greenhouse gas emissions. This idea holds great promise as a sustainable and environmentally friendly energy solution. In particular, many saccharide substrates, including monosaccharides, disaccharides, polysaccharides, etc., have been used as sacrificial reagents in photocatalytic reforming over the past few decades. Among the various substrates, cellulose has attracted worldwide attention since it is the most abundant polymeric biomass resource that can be obtained from many sources. Following, photo‐reforming of renewable lignocellulosic biomass, which aligns with the requirements of sustainable development, is successfully proposed. The overall catalytic efficiency will be discussed regarding the biohydrogen evolution rate (mmol gcat−1 h−1). Finally, the review concluded with challenges and potential opportunities to enhance biohydrogen are also given. [ABSTRACT FROM AUTHOR]

Electrode materials based on zinc molybdenum oxides were designed by the saccharide-assisted sol-gel procedure for electrochemical hydrogen storage (EHS). By using different characterization methods to observe the formation of nanostructures, it was possible to determine that carbon texture was present on the nanostructured surfaces of zinc molybdenum oxides. The effects of employing various saccharides (mono, di, and poly saccharides) as carbon sources and fuel on the microstructure, electrochemical behaviors, and purity of synthesized samples were compared. The growth of nanocomposites including Zn 2 Mo 3 O 8 , ZnMo 8 O 10 , and Mo 8 O 23 phases was facilitated by the saccharide. A charge-discharge method was used to build three-electrode cells and expose them to galvanostatic cycling. To ascertain the stability of electrode architectures, cycling performance at various rates was carried out. The samples' hydrogen storage capabilities were examined, and the sample generated with glucose showed an optimum capacity about 1017 mAhg−1 after 15th cycle. • Saccharide assisted sol-gel synthesis of carbonous zinc molybdate nanocomposites as electrode materials. • Investigation of crystallinity, microstrain and structural parameters. • The assessment of hydrogen storage activity using comparative chronopotentiometry study. • Understanding of redox and physisorption-based efficient storage mechanisms. [ABSTRACT FROM AUTHOR]

A novel metal–organic framework functionalized with amino and triazole moieties, namely Zn-TDA, has been synthesized. It represents the first example of a MOF-based sensor for highly selective sensing of cellobiose over other saccharides. Furthermore, Zn-TDA was used as a catalyst for the conversion of cellobiose to 5-hydroxymethylfurfural (5-HMF), achieving an excellent yield of 68.7% within 90 min under mild conditions. [ABSTRACT FROM AUTHOR]

Extensive utilization of renewable biomass is crucial for the progress of carbon neutral and carbon peak implementation. Wheat straw, as an important by-product of crops, is hardly ever efficiently utilized by conventional processes. Here, we proposed a mild acid-coupled-with-enzymatic-treatment process to realize the utilization of lignin and hemicelluloses from pulping liquor on the basis of the chemical–mechanical pulping process. The pulping liquor was treated with acid first to precipitate lignin, and it was further hydrolyzed with xylanase to obtain XOSs. The recovered lignin was characterized by FT-IR, 2D-HSQC, GPC, etc. It was found that lignin undergoes depolymerization and condensation during acid treatment. Also, saccharide loss enhanced with the decrease in pH due to the presence of the LCC structure. As a result, an optimized pH of 4 for the acid treatment ensured that the removal rate of lignin and loss rate of polysaccharides achieved 77.15% and 6.13%, respectively. Moreover, further xylanase treatment of the pulping liquor attained a recovery rate of 51.87% for XOSs. The study presents a new insight for the efficient utilization of lignin and hemicellulose products from non-woody materials in the prevailing biorefinery concept. [ABSTRACT FROM AUTHOR]

Summary: The study explores the enhanced functional and bioactive properties of Konjac Glucomannan Hydrolysate (KGMH) by partially degrading Konjac Glucomannan (KGM) using β‐mannanase over 60 min. KGM concentrations (40% and 50% w/w) were treated with 200–300 U g−1 of the enzyme over 60 min. The hydrolysis of KGM was monitored by colorimetry, with DP values ranging from 4.20 to 6.16 for 40% KGM and 4.10 to 4.60 for 50% KGM. MALDI‐TOF‐MS analysis confirmed typical oligosaccharides with DP values from 2 to 9 and some acetyl substitutions. The optimal conditions of 40% KGM with 250 U g−1 enzyme and varying hydrolysis times produced KGMHs with a wide range of DPs, demonstrating in vitro antioxidant and anti‐glycation activities. The results showed significant bioactivities (P < 0.05) positively correlated with lower DP values. This study emphasises the potential of KGMH as a novel functional food ingredient, highlighting its bioactive properties and the significant impact of DPs on the biological functionality of saccharides. [ABSTRACT FROM AUTHOR]

Summary: This study investigated the enhancement of food proteins through glycation with bioactive saccharides derived from Konjac glucomannan hydrolysate (KGMH) via the Maillard reaction. The focus was on how the degree of polymerisation (DP) of KGMH influences the glycation process and the properties of conjugates with chicken breast and soy proteins. KGMH samples with low, medium, and high DPs (4.20, 5.21, and 6.11, respectively) were glycated under wet‐heating conditions with varying pH levels (8, 9, and 10) at 70 °C for 15 min to 6 h. Results demonstrated that higher pH and longer reaction times significantly enhanced (P < 0.05) glycation and browning, particularly with lower DP saccharides. The optimal conjugates markedly improved protein solubility (1.3 to 1.9 times), heat stability (1.1 to 2.4 times), and emulsification properties (1.2 to 1.5 times), with the highest DP showing the strongest correlation. Additionally, these conjugates exhibited significantly enhanced in vitro bioaccessibility (58.69% to 66.65%) and antioxidant activity (P < 0.05). This study highlights the novel potential of KGMH‐protein conjugation through the Maillard reaction for developing functional food ingredients with superior quality. [ABSTRACT FROM AUTHOR]

The present study evaluated the potential of a saccharide mixture (galactose, glucose, fructose, and sucrose in a 2:1:1:1 ratio) as a chemoattractant (attraction) or/and feeding stimulant (ingestion) for the purple mud crab Scylla tranquebarica. In Experiment I, the S. tranquebarica appetitive response toward the 3%, 5%, or 7% (w/v) saccharide mixture solutions was examined and evaluated by a scoring method. The 5% and 7% treatments yielded the highest mean score (2.05 out of 3.00), with 20% of the S. tranquebarica exhibiting the highest response order (probing movement) in the latter treatment. In Experiment II, the S. tranquebarica feeding response toward the pelleted feeds containing the saccharide mixture at 3%, 5%, or 7% (SAC3, SAC5, or SAC7) was examined and evaluated using a scoring method. No significant difference (P > 0.05) was found among the mean scores of SAC3, SAC5, and SAC7. However, the mean score of the SAC7 diet was significantly higher (P < 0.05) than that of the control feed (without saccharide mixture inclusion), with 25% of the S. tranquebarica ingesting the feed. These findings highlight the potency of the saccharide mixture as a feeding effector for S. tranquebarica. [ABSTRACT FROM AUTHOR]

Glycoconjugate vaccines have been effective in preventing numerous bacterial infectious diseases and have shown recent potential to treat cancers through active immunotherapy. Soluble polysaccharides elicit short-lasting immune responses and are usually covalently linked to immunogenic carrier proteins to enhance the antigen-specific immune response by stimulating T-cell-dependent mechanisms. Nonetheless, the conjugation of purified polysaccharides to carrier proteins complexifies vaccine production, and immunization with protein glycoconjugates can lead to the undesirable immunogenic interference of the carrier. Recently, the use of nanoparticles and nanoassemblies for the delivery of antigenic saccharides has gathered attention from the scientific community. Nanoparticles can be easily functionalized with a diversity of functionalities, including T-cell epitope, immunomodulator and synthetic saccharides, allowing for the modulation and polarization of the glycoantigen-specific immune response. Notably, the conjugation of glycan to nanoparticles protects the antigens from degradation and enhances their uptake by immune cells. Different types of nanoparticles, such as liposomes assembled from lipids, inorganic nanoparticles, virus-like particles and dendrimers, have been explored for glycovaccine design. The versatility of nanoparticles and their ability to induce robust immune responses make them attractive delivery platforms for antigenic saccharides. The present review aims at summarizing recent advancements in the use of nano-scaled systems for the delivery of synthetic glycoantigens. After briefly presenting the immunological mechanisms required to promote a robust immune response against antigenic saccharides, this review will offer an overview of the current trends in the nanoparticle-based delivery of glycoantigens. [ABSTRACT FROM AUTHOR]

The industrial processes used to produce paper and cellulose generate many lignocellulosic residues. These residues are usually burned to produce heat to supply the energy demands of other processes, increasing greenhouse gas emissions and resulting in a high environmental impact. Instead of burning these lignocellulosic residues, they can be converted into saccharides, which are feedstock for high-value products and biofuels. Keggin heteropolyacids are efficient catalysts for obtaining saccharides from cellulose and hemicellulose and converting them into bioproducts or biofuel. Furfural, 5-hydroxymethylfurfural, levulinic acid, and alkyl levulinates are important platform molecules obtained from saccharides and raw materials in the biorefinery processes used to produce fine chemicals and biofuels. This review discusses the significant progress achieved in the development of the processes based on heteropolyacid-catalyzed reactions to convert biomass and their residues into furfural, 5-hydroxymethylfurfural, levulinic acid, and alkyl levulinates in homogeneous and heterogeneous reaction conditions. The different modifications that can be performed to a Keggin HPA structure, such as the replacement of the central atom (P or Si) with B or Al, the doping of the heteropolyanion with metal cations, and a proton exchange with metal or organic cations, as well as their impact on the catalytic activity of HPAs, are detailed and discussed herein. [ABSTRACT FROM AUTHOR]

Synthesis of Galβ1 → 3GlcNAc-repeating saccharides is limited mainly by the formation of less-reactive oxazolines. We herein report an expeditious approach that requires trichloroacetyloxazolines as reactive glycosyl donors. Using only two disaccharide building blocks, the iterative oxazoline formation and glycosylation synthesized hexa- and octasaccharides with overall yields of 47% and 26% in four and six steps, respectively. [ABSTRACT FROM AUTHOR]

Saccharides are involved in nearly all life processes. However, due to the complexity and diversity of saccharide structures, their selective recognition is one of the most challenging tasks. Distinct from conventional receptor designs that rely on delicate and complicated molecular structures, here a novel and precise ternary co‐assembled strategy is reported for achieving saccharide recognition, which originates from a halogen ions‐driven aggregation‐induced emission module called p‐Toluidine, N, N′‐1‐propen‐1‐yl‐3‐ylidene hydrochloride (PN‐Tol). It exhibits ultra‐strong self‐assembly capability and specifically binds to 4‐mercaptophenylboronic acid (MPBA), forming highly ordered co‐assemblies. Subsequent binding of various saccharides results in heterogeneous ternary assembly behaviors, generating cluster‐like, spherical, and rod‐like microstructures with well‐defined crystalline patterns, accompanied by significant enhancement of fluorescence. Owing to the excellent expandability of the PN module, an array sensor is constructed that enables easy classification of diverse saccharides, including epimer and optical isomers. This strategy demonstrates wide applicability and paves a new avenue for saccharide recognition, analysis, and sequencing. [ABSTRACT FROM AUTHOR]

The GT99 domain of the membrane‐anchored WbbB glycosyltransferase (WbbBGT99) catalyzes the transfer of 3‐deoxy‐D‐manno‐oct‐2‐acid (β‐Kdo) to an O‐antigen saccharide acceptor with retention of stereochemistry. It has been proposed that the enzyme follows an unprecedented double‐displacement mechanism involving the formation of covalent adduct between the Kdo sugar and an active site residue (Asp232) that is properly oriented for nucleophilic attack. Here we use QM/MM metadynamics simulations on recently reported crystal structures to provide theoretical evidence for the formation of such adduct and unveil the atomic details of the chemical reaction. Our results support the interpretation made on the basis of X‐ray and mass spectrometry analyses. Moreover, we show that the formation of the β‐Kdo‐Asp232 adduct is assisted by the sugar Kdo‐carboxylate group, which mediates the transfer of a proton from Asp232 towards the phosphate leaving group, alleviating electrostatic repulsion between the two negatively charged carboxylate groups. The computed mechanism also explains why His265, previously proposed to act as a general acid, does not impair catalysis. This mechanism can be extended to other related enzymes, expanding the repertoire of GT mechanisms in Nature. [ABSTRACT FROM AUTHOR]

The synthesis of 5‐(halomethyl)furfurals (XMFs, X=F, Cl, Br, I), including 5‐(chloromethyl)furfural (CMF), 5‐(bromomethyl)furfural (BMF), 5‐(iodomethyl)furfural (IMF), and 5‐(fluoromethyl)furfural (FMF), from biomass represents a pivotal advancement in renewable chemistry and engineering. Harnessing waste biomass as a raw material offers a sustainable alternative to fossil‐based resources, mitigating environmental degradation and addressing pressing energy needs. CMF and BMF, characterized by their enhanced stability over the hydroxyl analog, 5‐(hydroxymethyl)furfural (HMF), exhibit promise as renewable building blocks for scale‐up and commercialization. The surge in research interest, particularly from 2010 to 2024, reflects a growing recognition of XMFs′ potential as novel platform chemicals. This review highlights the evolution of XMF synthesis methods, focusing on their transformation from saccharides and lignocellulosic biomass. Mechanistic insights and experimental setups are scrutinized for industrial feasibility and scalability, shedding light on technical challenges and avenues for further research. The analysis underscores the burgeoning significance of XMFs in the transition towards sustainable chemical production, emphasizing the importance of process optimization and mechanistic understanding for commercial deployment. [ABSTRACT FROM AUTHOR]

Lipophosphoglycans (LPGs) are found on the surface of Leishmania, a protozoan parasite, and are immunologically important. Herein, disaccharide 1‐phosphate repeating units of LPGs were successfully synthesized on a solid support with high anomeric purity using a disaccharide α‐1‐phosphoramidite building block. To enhance solubility in the reaction solvent, hydroxy‐protecting groups in the form of para‐t‐butylbenzoyl were introduced to the building block. The saccharide chain was elongated via stable glycosyl boranophosphate linkages, followed by the conversion of inter‐sugar linkages to phosphodiester counterparts using an oxaziridine derivative. The addition of a silylating reagent post‐reaction with the oxaziridine derivative efficiently facilitated the conversion of boranophosohodiesters to phosphodiesters. This method enabled the α‐selective synthesis of up to 15 repeating units, marking the longest homogeneous repeating units of LPGs synthesized chemically. Given the chain length equivalence to native LPGs, the method developed herein holds promise for advancing anti‐Leishmanial pharmaceuticals and vaccines. [ABSTRACT FROM AUTHOR]

Autophagy of glycogen (glycophagy) is crucial for the maintenance of cellular glucose homeostasis and physiology in mammals. STBD1 can serve as an autophagy receptor to mediate glycophagy by specifically recognizing glycogen and relevant key autophagic factors, but with poorly understood mechanisms. Here, we systematically characterize the interactions of STBD1 with glycogen and related saccharides, and determine the crystal structure of the STBD1 CBM20 domain with maltotetraose, uncovering a unique binding mode involving two different oligosaccharide-binding sites adopted by STBD1 CBM20 for recognizing glycogen. In addition, we demonstrate that the LC3-interacting region (LIR) motif of STBD1 can selectively bind to six mammalian ATG8 family members. We elucidate the detailed molecular mechanism underlying the selective interactions of STBD1 with ATG8 family proteins by solving the STBD1 LIR/GABARAPL1 complex structure. Importantly, our cell-based assays reveal that both the STBD1 LIR/GABARAPL1 interaction and the intact two oligosaccharide binding sites of STBD1 CBM20 are essential for the effective association of STBD1, GABARAPL1, and glycogen in cells. Finally, through mass spectrometry, biochemical, and structural modeling analyses, we unveil that STBD1 can directly bind to the Claw domain of RB1CC1 through its LIR, thereby recruiting the key autophagy initiation factor RB1CC1. In all, our findings provide mechanistic insights into the recognitions of glycogen, ATG8 family proteins, and RB1CC1 by STBD1 and shed light on the potential working mechanism of STBD1-mediated glycophagy. [ABSTRACT FROM AUTHOR]

Multi-functional cysteine-targeting covalent warheads possess significant therapeutic potential in medicinal chemistry and chemical biology. Herein, we present novel unsaturated and asymmetric ketone (oxazolinosene) scaffolds that selectively conjugate cysteine residues of peptides and bovine serum albumin under normal physiological conditions. This unsaturated saccharide depletes GSH in NCI-H1299 cells, leading to anti-tumor effects in vitro. The acetyl group of the ketal moiety on the saccharide ring can be converted to other carboxylic acids in a one-pot synthesis. In this way, the loaded acid can be click-released during cysteine conjugation, making the oxazolinosene a potential multifunctional therapeutic agent. The reaction kinetic model for oxazolinosene conjugation to GSH is well established and was used to evaluate oxazolinosene reactivity. The aforementioned oxazolinosenes were stereoselectively synthesized via a one-step reaction of nitriles with saccharides and conveniently converted into a series of α, β-unsaturated ketone N-glycosides as prevalent synthetic building blocks. The reaction mechanisms of oxazolinosene synthesis were investigated through calculations and validated with control experiments. Overall, these oxazolinosenes can be easily synthesized and developed as cysteine-targeted covalent warheads carrying useful click-releasing groups. Multifunctional cysteine targeting covalent warheads possess significant therapeutic potential in medicinal chemistry and chemical biology. Here, the authors develop an oxazolinosene scaffold from nitrile groups and saccharides that can selectively conjugate cysteine residues within peptides and proteins under physiological conditions, as well as deplete glutathione in cancer cells. [ABSTRACT FROM AUTHOR]

In this investigation, we detail the synthesis of silver nanoparticles (AgNPs) via a precise chemical vacuum deposition (CVD) methodology, aimed at augmenting the analytical performance of laser desorption/ionization mass spectrometry (LDI-MS) for the detection of low-molecular-weight analytes. Employing a precursor supply rate of 0.0014 mg/s facilitated the formation of uniformly dispersed AgNPs, characterized by SEM and AFM to have an average diameter of 33.5 ± 1.5 nm and a surface roughness (Ra) of 11.8 nm, indicative of their homogeneous coverage and spherical morphology. XPS and SEM-EDX analyses confirmed the metallic silver composition of the nanoparticles with Ag peak splitting, reflecting the successful synthesis of metallic Ag. Comparative analytical evaluation with traditional MALDI matrices revealed that AgNPs significantly reduce signal suppression, thereby enhancing the sensitivity and specificity of LDI-MS for low-molecular-weight compounds such as triglycerides, saccharides, amino acids, and carboxylic acids. Notably, the application of AgNPs demonstrated a superior linear response for triglyceride signals with regression coefficients surpassing 0.99, markedly outperforming conventional matrices. The study further extends into quantitative analysis through nanoparticle-based laser desorption/ionization (NALDI), where AgNPs exhibited enhanced ionization efficiency, characterized by substantially lower limits of detection (LOD) and quantification (LOQ) for tested standards. Particular attention was paid to lipids with a detailed examination of their fragmentation pathways. These results highlight the significant potential of AgNPs synthesized via CVD to transform the analytical detection and quantification of low-molecular-weight compounds using NALDI. This approach offers a promising avenue for expanding the scope of analytical applications in mass spectrometry and introducing innovative methodologies for enhanced precision and sensitivity. [ABSTRACT FROM AUTHOR]

Background The use of stable carbon isotope ratios (δ13C) of sugar fractions of honey is a powerful tool to detect adulteration with sugar syrups. This is accomplished by calculating differences of the δ13C values between individual honey saccharides and comparing them to published purity criteria. A liquid chromatography–isotope ratio mass spectrometry (LC-IRMS) method for the determination of δ13C values of sugars in honey was previously validated by an interlaboratory comparison, but no further guidance was given how to include the obtained precision figures of the compound-specific δ13C values in the purity assessment of honey. Objective To use existing data to estimate the standard deviation of the repeatability (sr) and reproducibility (sR) of differences (Δ δ13C) between the δ13C values of individual honey saccharides. Methods Previously published δ13C values were used to calculate differences (Δ δ13C values) between δ13C fructose—δ13C glucose, δ13C glucose—δ13C disaccharides, etc. in a honey sample; sr and sR of Δ δ13C values were calculated according to ISO 5725–2:2019. Results The Δ δ13C sr and sR values were essentially of the same magnitude as the sr and sR values of δ13C values of the sugar fractions. The precision of the Δ δ13C values was used to estimate the critical difference for comparing a test result with a reference value according to ISO 5725–6:1994. This varied between 0.26 and 1.10‰. Conclusion The estimated critical differences can be used to determine whether a honey test result complies with published Δ δ13C purity criteria. Highlight The proposed procedure will increase confidence in decisions based on compound-specific δ13C values regarding the conformity of honey with published purity criteria. [ABSTRACT FROM AUTHOR]

Quasi‐tetrahedral o‐azophenylboronic acid (azoB‐ROH), which contains the protic solvent ROH, is a key species in the colorimetric sensing of saccharides by o‐azophenylboronic acid (azoB). In this study, we compared the reactivity of azoB‐ROH with that of trigonal azoB and tetrahedral o‐azophenylboronate (azoB‐OH−), and clarified the reaction mechanism of azoB‐ROH with cis‐1,2‐cyclopentanediol and D‐glucose. Analysis of the kinetics of the reactions of azoB with cis‐1,2‐cyclopentanediol and D‐glucose in DMSO:water = 1:9 and azoB with cis‐1,2‐cyclopentanediol in tetrahydrofuran containing a small amount of methanol revealed that there was not much difference in the reactivity of azoB‐H2O and azoB‐OH−, although the reactivity of azoB was higher than that of azoB‐MeOH, that is, the reaction mechanism of azoB‐H2O was essentially the same as that of azoB‐OH−. [ABSTRACT FROM AUTHOR]

As a protein extracted from soybeans, soy protein isolate (SPI) may undergo the Maillard reaction (MR) with co-existing saccharides during the processing of soy-containing foods, potentially altering its structural and functional properties. This work aimed to investigate the effect of mono- and polysaccharides on the structure and functional properties of SPI during MR. The study found that compared to oat β-glucan, the reaction rate between SPI and D-galactose was faster, leading to a higher degree of glycosylation in the SPI–galactose conjugate. D-galactose and oat β-glucan showed different influences on the secondary structure of SPI and the microenvironment of its hydrophobic amino acids. These structural variations subsequently impact a variety of the properties of the SPI conjugates. The SPI–galactose conjugate exhibited superior solubility, surface hydrophobicity, and viscosity. Meanwhile, the SPI–galactose conjugate possessed better emulsifying stability, capability to produce foam, and stability of foam than the SPI–β-glucan conjugate. Interestingly, the SPI–β-glucan conjugate, despite its lower viscosity, showed stronger hypoglycemic activity, potentially due to the inherent activity of oat β-glucan. The SPI–galactose conjugate exhibited superior antioxidant properties due to its higher content of hydroxyl groups on its molecules. These results showed that the type of saccharides had significant influences on the SPI during MR. [ABSTRACT FROM AUTHOR]

Chemical-nose/tongue technologies are emerging as promising analytical tools for glycan analysis. After briefly introducing the importance of glycans and their analytical methods, including the lectin microarray (LMA) as one of the gold standards, the fundamental principles underlying chemical noses/tongues are explained and various applications for monosaccharides and glycans are introduced. Then, the similarities and differences of these two approaches are discussed. While both technologies aim to comprehensively profile biospecimens based on ‘interaction patterns’ between multiple recognition probes and analytes, each has its own strengths. LMAs excel at specific, targeted analysis based on defined lectin–glycan interactions, whereas chemical nose/tongue offers greater flexibility and expandability in terms of system design, making it well-suited for discovering unknown glycan profiles and detecting broader differences in glycan mixtures. In the future, chemical-nose/tongue technologies may be applied to niche areas in glycan analysis and become powerful tools that complement LMA techniques.

The quest for environmentally benign flame-retardant plastic additives has gained significant attention in recent years due to the harmful environmental effects of conventional flame-retardant additives on human health and the environment. Discussed in this review are the very latest developments in multi-component flame retardants comprising at least one of their elements as a bio-derived phenol, a poly/saccharide derivative, or a greener phosphorus source. Chief among these green additives discussed are tannins, lignin/lignans, alginate, cellulose, starch, chitosan, and phytic acid. The representative studies discussed herein demonstrate the potential of these greener alternatives to enhance the flame retardancy, thermal stability, and smoke suppression properties of various polymers, including polyurethane, polylactic acid, epoxy resin, and polypropylene. A table summarizing key metrics for assessing fire retardancy is provided as a convenient reference. In concluding the review, several future directions and cautionary notes for future work in the field are discussed, including the need to optimize flame-retardant systems, assessing the impact of flame retardant additives on polymer mechanical properties, the practical, technical, and economic factors involved in scaling up production of plastics incorporating green flame-retardant additives, and assessing the long-term environmental impact of such additives.

In this paper, the effects of three postharvest treatments (aerobic,vacuum,vacuum+1-MCP) on browning, active oxygen metabolism and saccharides during storage of deastringent persimmon were researched. Meanwhile, the correlations between browning and other indexes were analyzed. BI of vacuum and vacuum+1-MCP was lower than that in aerobic group, and the browning degree in vacuum+1-MCP group was the lowest. The SOD and APX activities of the three kinds of persimmon treated after harvest decreased and increased respectively, and the SOD activities of the vacuum group were the lowest，the APX activities under vacuum and vacuum+1-MCP conditions were higher than that in aerobic group. At vacuum and vacuum+1-MCP conditions，the increase of CAT activity of persimmon was inhibited, and the accumulation of H2O2 was reduced, with lower ability to inhibit hydroxyl radical and ascorbic acid content. The reducing sugar content of persimmon in vacuum and vacuum+1-MCP groups was lower than that in aerobic group, and the increase in vacuum+1-MCP group was the slowest, from 14.10% at the beginning of storage to 14.87% on 12 d. The pectin content of persimmon in vacuum+1-MCP group decreased slowly. Correlation analysis showed that the correlations between browning and various indexes under different postharharvest treatments were different. The persimmon BI was always negatively correlated with pectin, meanwhile positively correlated with reducing sugar. It can be concluded that vacuum and vacuum+1-MCP conditions are more conducive to inhibiting the browning of persimmon after deastringent.

Glycoconjugate vaccines are based on chemical conjugation of pathogen‐associated carbohydrates with immunogenic carrier proteins and are considered a very cost‐effective way to prevent infections. Most of the licensed glycoconjugate vaccines are composed of saccharide antigens extracted from bacterial sources. However, synthetic oligosaccharide antigens have become a promising alternative to natural polysaccharides with the advantage of being well‐defined structures providing homogeneous conjugates. Haemophilus influenzae (Hi) is responsible for a number of severe diseases. In recent years, an increasing rate of invasive infections caused by Hi serotype a (Hia) raised some concern, because no vaccine targeting Hia is currently available. The capsular polysaccharide (CPS) of Hia is constituted by phosphodiester‐linked 4‐β‐d‐glucose‐(1→4)‐d‐ribitol‐5‐(PO4→) repeating units and is the antigen for protein‐conjugated polysaccharide vaccines. To investigate the antigenic potential of the CPS from Hia, we synthesized related saccharide fragments containing up to five repeating units. Following the synthetic optimization of the needed disaccharide building blocks, they were assembled using the phosphoramidite approach for the installation of the phosphodiester linkages. The resulting CPS‐based Hia oligomers were conjugated to CRM197 carrier protein and evaluated in vivo for their immunogenic potential, showing that all glycoconjugates were capable of raising antibodies recognizing Hia synthetic fragments. [ABSTRACT FROM AUTHOR]

Saccharides, being one of the fundamental molecules of life, play essential roles in the physiological and pathological functions of cells. However, their intricate structures pose challenges for detection. Nanopore technology, with its high sensitivity and capability for single-molecule-level analysis, has revolutionized the identification and structural analysis of saccharide molecules. This review focuses on recent advancements in nanopore technology for carbohydrate detection, presenting an array of methods that leverage the molecular complexity of saccharides. Biological nanopore techniques utilize specific protein binding or pore modifications to trigger typical resistive pulses, enabling the high-sensitivity detection of monosaccharides and oligosaccharides. In solid-state nanopore sensing, boronic acid modification and pH gating mechanisms are employed for the specific recognition and quantitative analysis of polysaccharides. The integration of artificial intelligence algorithms can further enhance the accuracy and reliability of analyses. Serving as a crucial tool in carbohydrate detection, we foresee significant potential in the application of nanopore technology for the detection of carbohydrate molecules in disease diagnosis, drug screening, and biosensing, fostering innovative progress in related research domains. [ABSTRACT FROM AUTHOR]

Leaf litter microbes collectively degrade plant polysaccharides, influencing land–atmosphere carbon exchange. An open question is how substrate complexity—defined as the structure of the saccharide and the amount of external processing by extracellular enzymes—influences species interactions. We tested the hypothesis that monosaccharides (i.e. xylose) promote negative interactions through resource competition, and polysaccharides (i.e. xylan) promote neutral or positive interactions through resource partitioning or synergism among extracellular enzymes. We assembled a three-species community of leaf litter-degrading bacteria isolated from a grassland site in Southern California. In the polysaccharide xylan, pairs of species stably coexisted and grew equally in coculture and in monoculture. Conversely, in the monosaccharide xylose, competitive exclusion and negative interactions prevailed. These pairwise dynamics remained consistent in a three-species community: all three species coexisted in xylan, while only two species coexisted in xylose, with one species capable of using peptone. A mathematical model showed that in xylose these dynamics could be explained by resource competition. Instead, the model could not predict the coexistence patterns in xylan, suggesting other interactions exist during biopolymer degradation. Overall, our study shows that substrate complexity influences species interactions and patterns of coexistence in a synthetic microbial community of leaf litter degraders. [ABSTRACT FROM AUTHOR]

The global demand for plant oil has reached unprecedented levels and is relevant in all industrial sectors. Driven by the growing awareness for environmental issues of traditional plant oils and the need for eco-friendly alternatives, microbial oil emerges as a promising product with significant potential. Harnessing the capabilities of oleaginous microorganisms is an innovative approach for achieving sustainable oil production. To increase economic feasibility, it is crucial to explore feedstocks such as agricultural waste streams as renewable resource for microbial bioprocesses. The fungal model Ustilago maydis is one promising organism in the field of microbial triglyceride production. It has the ability to metabolize a wide variety of carbon sources for cell growth and accumulates high amounts of triglycerides intracellularly. In this study we asked whether this large variety of usable carbon sources can also be utilized for triglyceride production, using corn stover saccharides as a showcase. Our experiments revealed metabolization of the major saccharide building blocks present in corn stover, demonstrating the remarkable potential of U. maydis. The microorganism exhibited the capacity to synthesize triglycerides using the saccharides glucose, fructose, sucrose, xylose, arabinose, and galactose as carbon source. Notably, while galactose has been formerly considered as toxic to U. maydis, we found that the fungus can metabolize this saccharide, albeit with an extended lag phase of around 100 hours. We identified two distinct methods to significantly reduce or even prevent this lag phase, challenging previous assumptions and expanding the understanding of U. maydis metabolism. Our findings suggest that the two tested methods can prevent long lag phases on feedstocks with high galactose content and that U. maydis can produce microbial triglycerides very efficiently on many different carbon sources. Looking forward, exploring the metabolic capabilities of U. maydis on additional polymeric components of corn stover and beyond holds promise for innovative applications, marking a significant step toward environmentally sustainable bioprocessing technologies. [ABSTRACT FROM AUTHOR]

We report the synthesis of arsenic heterocycles derived from saccharides 2–4 and AsCl3. Compounds 5 and 6 are stable in aqueous solutions, DMSO, or methanolic solutions. However, NMR and HPLC studies revealed that intramolecular trans‐esterification processes leads to dynamic equilibria. Theoretical studies revealed that three arsenates and two arsoranes participate in these intramolecular equilibria and account for the experimental spectroscopy and HPLC results. Through the correlation between the experimental and theoretical 13C NMR spectra, we proposed the speciation of arsenic Compounds 5 and 6. Moreover, experimental and theoretical IR spectra demonstrated that arsenates 5 A and 6 A predominate in the solid state. QTAIM studies were performed to explain the chemical shifts in the 13C NMR spectra. Biological studies suggest that the structural flexibility of Compounds 5 and 6 increase the cytotoxic and antiproliferative activities of these compounds. [ABSTRACT FROM AUTHOR]

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Herein based on literature available a hypothesis is provided about molecular basis for initial events in establishment interactions. This hypothesis asserts that: "recognition and interaction that occur between organisms is prearranged. There are membrane receptors with or without soluble components derived from the respective organisms that bridge specific interactions". Organisms' prearranged recognition theory (OPRT) can be specifically applied to host-microbe interactions where most microbes are coated (opsonised) by soluble components (opsonins) from the host, but there are also some microbes that can bypass host opsonization expressing receptors for the host cells or secreting host's opsonin-like molecules. The receptors involved in organism's interactions, their specificity and repertoire depend on saccharides from glycoproteins, glycolipids, and polysaccharides (glycans) which are abundant extracellular components. Based in OPRT is possible to explain species-specific interactions and several other phenomena, such as hyper-infectivity, tissue tropism, differential sensitivity to disease depending on type O-blood, and tumoral cell promiscuity. The lipid raft domain in cellular membrane is proposed as the main location where interactions will trigger cellular responses. Possible scientific and biotechnology applications and alternative routes to modify organism's interactions and consequences are discussed. It is a novel hypothesis regarding the degree to which an organism's interactions are prearranged and the role of saccharides epitopes. [ABSTRACT FROM AUTHOR]

Due to the presence of the boronic acid moieties, poly-3-thienylboronic acid has an affinity for saccharides and other diol-containing compounds. Thin films of this novel chemosensitive polymer were synthesized electrochemically on the gold surface. The adhesion of the polymer was enhanced by the deposition of a monomolecular layer of thiophenol. The technology was used to fabricate conductometric sensors for glucose and other diol-containing compounds. Simultaneous two- and four-electrode conductivity measurements were performed. The chemical sensitivity to sorbitol, fructose, glucose, and ethylene glycol was studied at different pH and electrode potentials, and the corresponding binding constants were obtained. Depending on the electrode potential, the reciprocal values of the binding constants of glucose to poly-3-thienylboronic acid at neutral pH are in the range of 0.2 mM–1.0 mM. The affinity for glucose has been studied in buffer solutions and in solutions containing the major components of human blood. It was shown that the presence of human serum albumin increases the affinity of poly-3-thienylboronic acid for diol-containing compounds. [ABSTRACT FROM AUTHOR]