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2. A perfusion host‐microbe bioreactor (HMB) system that captures dynamic interactions of secreted metabolites between epithelial cells cocultured with a human gut anaerobe.

Author

Yang, Jingyun, Cassaday, Jason, Wyche, Thomas P., Squadroni, Brian, Newhard, William, Trinh, Huong, Cabral, Damien, Hett, Erik, Sana, Theodore R., Lee, Kyongbum, and Kasper, Stephen

Abstract

The human microbiota impacts a variety of diseases and responses to therapeutics. Due to a lack of robust in vitro models, detailed mechanistic explanations of host‐microbiota interactions cannot often be recapitulated. We describe the design and development of a novel, versatile and modular in vitro system that enables indirect coculture of human epithelial cells with anaerobic bacteria for the characterization of host‐microbe secreted metabolite interactions. This system was designed to compartmentalize anaerobes and human cells in separate chambers conducive to each organism's requisite cell growth conditions. Using perfusion, fluidic mixing, and automated sample collection, the cells continuously received fresh media, while in contact with their corresponding compartments conditioned supernatant. Supernatants from each chamber were collected in a cell‐free time‐resolved fashion. The system sustained low oxygen conditions in the anaerobic chamber, while also supporting the growth of a representative anaerobe (Bacteroides thetaiotaomicron) and a human colonic epithelial cell line (Caco‐2) in the aerobic chamber. Caco‐2 global gene expression changes in response to coculture with B. thetaiotaomicron was characterized using RNA sequencing. Extensive, targeted metabolomics analysis of over 150 central carbon metabolites was performed on the serially collected supernatants. We observed broad metabolite changes in host‐microbe coculture, compared to respective mono‐culture controls. These effects were dependent both on sampling time and the compartment probed (apical vs. basolateral). Coculturing resulted in the depletion of several important metabolites, including guanine, uridine 5'‐monophosphate, asparagine, and thiamine. Additionally, while Caco‐2 cells cultured alone predominantly affected the basolateral metabolite milieu, increased abundance of 2,3‐dihydroxyisovalerate and thymine on the basolateral side, occurred when the cells were cocultured with B. thetaiotaomicron. Thus, our system can capture the dynamic, competitive and cooperative processes between host cells and gut microbes. [ABSTRACT FROM AUTHOR]

Published
2024
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3. Discovery of Reactive Microbiota-Derived Metabolites that Inhibit Host Proteases.

Author

Guo, Chun-Jun, Chang, Fang-Yuan, Wyche, Thomas P, Backus, Keriann M, Acker, Timothy M, Funabashi, Masanori, Taketani, Mao, Donia, Mohamed S, Nayfach, Stephen, Pollard, Katherine S, Craik, Charles S, Cravatt, Benjamin F, Clardy, Jon, Voigt, Christopher A, and Fischbach, Michael A

Subjects
Feces, Animals, Humans, Bacteria, Bacillus subtilis, Escherichia coli, Pyrazines, Peptide Synthases, Phylogeny, Microbiota, Gastrointestinal Microbiome, biosynthetic gene cluster, metagenomics, microbiome, natural products, peptide aldehyde, protease inhibitor, synthetic biology, Developmental Biology, Biological Sciences, Medical and Health Sciences
Abstract

The gut microbiota modulate host biology in numerous ways, but little is known about the molecular mediators of these interactions. Previously, we found a widely distributed family of nonribosomal peptide synthetase gene clusters in gut bacteria. Here, by expressing a subset of these clusters in Escherichia coli or Bacillus subtilis, we show that they encode pyrazinones and dihydropyrazinones. At least one of the 47 clusters is present in 88% of the National Institutes of Health Human Microbiome Project (NIH HMP) stool samples, and they are transcribed under conditions of host colonization. We present evidence that the active form of these molecules is the initially released peptide aldehyde, which bears potent protease inhibitory activity and selectively targets a subset of cathepsins in human cell proteomes. Our findings show that an approach combining bioinformatics, synthetic biology, and heterologous gene cluster expression can rapidly expand our knowledge of the metabolic potential of the microbiota while avoiding the challenges of cultivating fastidious commensals.

Published
2017

5. Near-Infrared Photoredox Catalyzed Fluoroalkylation Strategy for Protein Labeling in Complex Tissue Environments

Author

Ryu, Keun Ah, primary, Reyes-Robles, Tamara, additional, Wyche, Thomas P., additional, Bechtel, Tyler J., additional, Bertoch, Jayde M., additional, Zhuang, Jin, additional, May, Christopher, additional, Scandore, Cody, additional, Dephoure, Noah, additional, Wilhelm, Sharon, additional, Quasem, Ishtiaque, additional, Yau, Annika, additional, Ingale, Sampat, additional, Szendrey, Andrew, additional, Duich, Margaret, additional, Oslund, Rob C., additional, and Fadeyi, Olugbeminiyi O., additional

Published
2024
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7. Metabolomics and Lipidomics Analyses Aid Model Classification of Type 2 Diabetes in Non-Human Primates.

Author

Tao, Peining, Conarello, Stacey, Wyche, Thomas P., Zhang, Nanyan Rena, Chng, Keefe, Kang, John, and Sana, Theodore R.

Subjects
TYPE 2 diabetes, LIPIDOMICS, METABOLOMICS, BILE acids, ANIMAL diseases, BLOOD lipids, FARNESOID X receptor, GLYCOCONJUGATES, CALPROTECTIN
Abstract

Type 2 diabetes (T2D) is a global public health issue characterized by excess weight, abdominal obesity, dyslipidemia, hyperglycemia, and a progressive increase in insulin resistance. Human population studies of T2D development and its effects on systemic metabolism are confounded by many factors that cannot be controlled, complicating the interpretation of results and the identification of early biomarkers. Aged, sedentary, and overweight/obese non-human primates (NHPs) are one of the best animal models to mimic spontaneous T2D development in humans. We sought to identify and distinguish a set of plasma and/or fecal metabolite biomarkers, that have earlier disease onset predictability, and that could be evaluated for their predictability in subsequent T2D studies in human cohorts. In this study, a single plasma and fecal sample was collected from each animal in a colony of 57 healthy and dysmetabolic NHPs and analyzed for metabolomics and lipidomics. The samples were comprehensively analyzed using untargeted and targeted LC/MS/MS. The changes in each animal's disease phenotype were monitored using IVGTT, HbA1c, and other clinical metrics, and correlated with their metabolic profile. The plasma and fecal lipids, as well as bile acid profiles, from Healthy, Dysmetabolic (Dys), and Diabetic (Dia) animals were compared. Following univariate and multivariate analyses, including adjustments for weight, age, and sex, several plasma lipid species were identified to be significantly different between these animal groups. Medium and long-chain plasma phosphatidylcholines (PCs) ranked highest at distinguishing Healthy from Dys animals, whereas plasma triglycerides (TG) primarily distinguished Dia from Dys animals. Random Forest (RF) analysis of fecal bile acids showed a reduction in the secondary bile acid glycoconjugate, GCDCA, in diseased animals (AUC 0.76[0.64, 0.89]). Moreover, metagenomics results revealed several bacterial species, belonging to the genera Roseburia, Ruminococcus, Clostridium, and Streptococcus, to be both significantly enriched in non-healthy animals and associated with secondary bile acid levels. In summary, our results highlight the detection of several elevated circulating plasma PCs and microbial species associated with fecal secondary bile acids in NHP dysmetabolic states. The lipids and metabolites we have identified may help researchers to differentiate individual NHPs more precisely between dysmetabolic and overtly diabetic states. This could help assign animals to study groups that are more likely to respond to potential therapies where a difference in efficacy might be anticipated between early vs. advanced disease. [ABSTRACT FROM AUTHOR]

Published
2024
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8. Very early life microbiome and metabolome correlates with primary vaccination variability in children

Author

Shaffer, Michael, primary, Best, Katharine, additional, Tang, Catherine, additional, Liang, Xue, additional, Schulz, Steven, additional, Gonzalez, Eduardo, additional, White, Cory H., additional, Wyche, Thomas P., additional, Kang, John, additional, Wesseling, Hendrik, additional, Topçuoğlu, Begüm D., additional, Cairns, Thomas, additional, Sana, Theodore R., additional, Kaufhold, Robin M., additional, Maritz, Julia M., additional, Woelk, Christopher H., additional, Swaminathan, Gokul, additional, Norton, James E., additional, and Pichichero, Michael E., additional

Published
2023
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10. Near-Infrared Photoredox Catalyzed Tryptophan Functionalization for Peptide Stapling and Protein Labeling in Complex Tissue Environments

Author

Ryu, Keun Ah, primary, Reyes-Robles, Tamara, additional, Wyche, Thomas P., additional, Bechtel, Tyler J., additional, Bertoch, Jayde M., additional, Zhuang, Jin, additional, May, Christopher, additional, Wilhelm, Sharon, additional, Quasem, Ishtiaque, additional, Yau, Annika, additional, Ingale, Sampat, additional, Szendrey, Andrew, additional, Duich, Margaret, additional, Oslund, Rob C., additional, and Fadeyi, Olugbeminiyi O., additional

Published
2022
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17. Bacterial Autoimmune Drug Metabolism Transforms an Immunomodulator into Structurally and Functionally Divergent Antibiotics

Author

Park, Hyun Bong, primary, Goddard, Tyler N., additional, Oh, Joonseok, additional, Patel, Jaymin, additional, Wei, Zheng, additional, Perez, Corey E., additional, Mercado, Brandon Q., additional, Wang, Rurun, additional, Wyche, Thomas P., additional, Piizzi, Grazia, additional, Flavell, Richard A., additional, and Crawford, Jason M., additional

Published
2020
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18. MS-Derived Isotopic Fine Structure Reveals Forazoline A as a Thioketone-Containing Marine-Derived Natural Product

Author

Zhang, Fan, primary, Wyche, Thomas P., additional, Zhu, Yanlong, additional, Braun, Doug R., additional, Yan, Jia-Xuan, additional, Chanana, Shaurya, additional, Ge, Ying, additional, Guzei, Ilia A., additional, Chevrette, Marc G., additional, Currie, Cameron R., additional, Thomas, Michael G., additional, Rajski, Scott R., additional, and Bugni, Tim S., additional

Published
2020
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19. Characterization of Autoinducer-3 Structure and Biosynthesis in E. coli

Author

Kim, Chung Sub, primary, Gatsios, Alexandra, additional, Cuesta, Santiago, additional, Lam, Yick Chong, additional, Wei, Zheng, additional, Chen, Haiwei, additional, Russell, Regan M., additional, Shine, Emilee E., additional, Wang, Rurun, additional, Wyche, Thomas P., additional, Piizzi, Grazia, additional, Flavell, Richard A., additional, Palm, Noah W., additional, Sperandio, Vanessa, additional, and Crawford, Jason M., additional

Published
2020
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20. Discovery of Reactive Microbiota-Derived Metabolites that Inhibit Host Proteases

Author

Massachusetts Institute of Technology. Department of Biological Engineering, Massachusetts Institute of Technology. Synthetic Biology Center, Chang, Fang-Yuan, Voigt, Christopher A., Guo, Chun-Jun, Wyche, Thomas P., Backus, Keriann M., Acker, Timothy M., Funabashi, Masanori, Taketani, Mao, Donia, Mohamed S., Nayfach, Stephen, Pollard, Katherine S., Craik, Charles S., Cravatt, Benjamin F., Clardy, Jon, Fischbach, Michael A., Massachusetts Institute of Technology. Department of Biological Engineering, Massachusetts Institute of Technology. Synthetic Biology Center, Chang, Fang-Yuan, Voigt, Christopher A., Guo, Chun-Jun, Wyche, Thomas P., Backus, Keriann M., Acker, Timothy M., Funabashi, Masanori, Taketani, Mao, Donia, Mohamed S., Nayfach, Stephen, Pollard, Katherine S., Craik, Charles S., Cravatt, Benjamin F., Clardy, Jon, and Fischbach, Michael A.

Abstract

The gut microbiota modulate host biology in numerous ways, but little is known about the molecular mediators of these interactions. Previously, we found a widely distributed family of nonribosomal peptide synthetase gene clusters in gut bacteria. Here, by expressing a subset of these clusters in Escherichia coli or Bacillus subtilis, we show that they encode pyrazinones and dihydropyrazinones. At least one of the 47 clusters is present in 88% of the National Institutes of Health Human Microbiome Project (NIH HMP) stool samples, and they are transcribed under conditions of host colonization. We present evidence that the active form of these molecules is the initially released peptide aldehyde, which bears potent protease inhibitory activity and selectively targets a subset of cathepsins in human cell proteomes. Our findings show that an approach combining bioinformatics, synthetic biology, and heterologous gene cluster expression can rapidly expand our knowledge of the metabolic potential of the microbiota while avoiding the challenges of cultivating fastidious commensals. Keywords: microbiome; natural products; synthetic biology; metagenomics; biosynthetic gene cluster; peptide aldehyde; protease inhibitor

Published
2018

22. Chemical Metagenomics of an Anti-HIV Compound From Uncultivated Symbionts

Author

Smith, Thomas E., primary, Pond, Christopher D., additional, Pierce, Elizabeth, additional, Harmer, Zachary P., additional, Kwan, Jason, additional, Zachariah, Malcom M., additional, Harper, Mary Kay, additional, Wyche, Thomas P., additional, Matainaho, Teatulohi K., additional, Bugni, Tim S., additional, Barrows, Louis R., additional, Ireland, Chris M., additional, and Schmidt, Eric W., additional

Published
2018
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23. Accessing chemical diversity from the uncultivated symbionts of small marine animals

Author

Smith, Thomas E, primary, Pond, Christopher D, additional, Pierce, Elizabeth, additional, Harmer, Zachary P, additional, Kwan, Jason, additional, Zachariah, Malcolm M, additional, Harper, Mary Kay, additional, Wyche, Thomas P, additional, Matainaho, Teatulohi K, additional, Bugni, Tim S, additional, Barrows, Louis R, additional, Ireland, Chris M, additional, and Schmidt, Eric W, additional

Published
2018
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24. Macrotermycins A-D, glycosylated macrolactams from a termite-associated Amycolatopsis sp. M39

Author

Beemelmanns, Christine, Ramadhar, Timothy R., Kim, Ki Hyun, Klassen, Jonathan L., Cao, Shugeng, Wyche, Thomas P., Hou, Yanpeng, Thomas-Poulsen, Michael, Bugni, Tim S., Currie, Cameron R., Clardy, Jon, Beemelmanns, Christine, Ramadhar, Timothy R., Kim, Ki Hyun, Klassen, Jonathan L., Cao, Shugeng, Wyche, Thomas P., Hou, Yanpeng, Thomas-Poulsen, Michael, Bugni, Tim S., Currie, Cameron R., and Clardy, Jon

Published
2017

26. Chemical Genomics, Structure Elucidation, and in Vivo Studies of the Marine-Derived Anticlostridial Ecteinamycin

Author

Wyche, Thomas P., primary, Alvarenga, René F. Ramos, additional, Piotrowski, Jeff S., additional, Duster, Megan N., additional, Warrack, Simone R., additional, Cornilescu, Gabriel, additional, De Wolfe, Travis J., additional, Hou, Yanpeng, additional, Braun, Doug R., additional, Ellis, Gregory A., additional, Simpkins, Scott W., additional, Nelson, Justin, additional, Myers, Chad L., additional, Steele, James, additional, Mori, Hirotada, additional, Safdar, Nasia, additional, Markley, John L., additional, Rajski, Scott R., additional, and Bugni, Tim S., additional

Published
2017
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27. Progressive Stereo Locking (PSL): A Residual Dipolar Coupling Based Force Field Method for Determining the Relative Configuration of Natural Products and Other Small Molecules

Author

Cornilescu, Gabriel, primary, Ramos Alvarenga, René F., additional, Wyche, Thomas P., additional, Bugni, Tim S., additional, Gil, Roberto R., additional, Cornilescu, Claudia C., additional, Westler, William M., additional, Markley, John L., additional, and Schwieters, Charles D., additional

Published
2017
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31. Chemical Genomics, Structure Elucidation, and in VivoStudies of the Marine-Derived Anticlostridial Ecteinamycin

Author

Wyche, Thomas P., Alvarenga, René F. Ramos, Piotrowski, Jeff S., Duster, Megan N., Warrack, Simone R., Cornilescu, Gabriel, De Wolfe, Travis J., Hou, Yanpeng, Braun, Doug R., Ellis, Gregory A., Simpkins, Scott W., Nelson, Justin, Myers, Chad L., Steele, James, Mori, Hirotada, Safdar, Nasia, Markley, John L., Rajski, Scott R., and Bugni, Tim S.

Abstract

A polyether antibiotic, ecteinamycin (1), was isolated from a marine Actinomadurasp., cultivated from the ascidian Ecteinascidia turbinata. 13C enrichment, high resolution NMR spectroscopy, and molecular modeling enabled elucidation of the structure of 1, which was validated on the basis of comparisons with its recently reported crystal structure. Importantly, ecteinamycin demonstrated potent activity against the toxigenic strain of Clostridium difficileNAP1/B1/027 (MIC = 59 ng/μL), as well as other toxigenic and nontoxigenic C. difficileisolates both in vitroand in vivo. Additionally, chemical genomics studies using Escherichia colibarcoded deletion mutants led to the identification of sensitive mutants such as trkAand kdpDinvolved in potassium cation transport and homeostasis supporting a mechanistic proposal that ecteinamycin acts as an ionophore antibiotic. This is the first antibacterial agent whose mechanism of action has been studied using E. colichemical genomics. On the basis of these data, we propose ecteinamycin as an ionophore antibiotic that causes C. difficiledetoxification and cell death viapotassium transport dysregulation.

Published
2024
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32. Progressive Stereo Locking (PSL): A Residual Dipolar Coupling Based Force Field Method for Determining the Relative Configuration of Natural Products and Other Small Molecules

Author

Cornilescu, Gabriel, Ramos Alvarenga, René F., Wyche, Thomas P., Bugni, Tim S., Gil, Roberto R., Cornilescu, Claudia C., Westler, William M., Markley, John L., and Schwieters, Charles D.

Abstract

Establishing the relative configuration of a bioactive natural product represents the most challenging part in determining its structure. Residual dipolar couplings (RDCs) are sensitive probes of the relative spatial orientation of internuclear vectors. We adapted a force field structure calculation methodology to allow free sampling of both Rand Sconfigurations of the stereocenters of interest. The algorithm uses a floating alignment tensor in a simulated annealing protocol to identify the conformations and configurations that best fit experimental RDC and distance restraints (from NOE and J-coupling data). A unique configuration (for rigid molecules) or a very small number of configurations (for less rigid molecules) of the structural models having the lowest chiral angle energies and reasonable magnitudes of the alignment tensor are provided as the best predictions of the unknown configuration. For highly flexible molecules, the progressive locking of their stereocenters into their statistically dominant Ror Sstate dramatically reduces the number of possible relative configurations. The result is verified by checking that the same configuration is obtained by initiating the locking from different regions of the molecule. For all molecules tested having known configurations (with conformations ranging from mostly rigid to highly flexible), the method accurately determined the correct configuration.

Published
2024
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37. Forazoline A: marine-derived polyketide with antifungal in vivo efficacy

Author

Wyche, Thomas P., Piotrowski, Jeff S., Hou, Yanpeng, Braun, Doug, Deshpande, Raamesh, McIlwain, Sean, Ong, Irene M., Myers, Chad L., Guzei, Ilia A., Westler, William M., Andes, David R., Bugni, Tim S., Wyche, Thomas P., Piotrowski, Jeff S., Hou, Yanpeng, Braun, Doug, Deshpande, Raamesh, McIlwain, Sean, Ong, Irene M., Myers, Chad L., Guzei, Ilia A., Westler, William M., Andes, David R., and Bugni, Tim S.

Abstract

Forazoline A, a novel antifungal polyketide with in vivo efficacy against Candida albicans, was discovered using LCMS-based metabolomics to investigate marine-invertebrate-associated bacteria. Forazoline A had a highly unusual and unprecedented skeleton. Acquisition of 13C–13C gCOSY and 13C–15N HMQC NMR data provided the direct carbon–carbon and carbon–nitrogen connectivity, respectively. This approach represents the first example of determining direct 13C–15N connectivity for a natural product. Using yeast chemical genomics, we propose that forazoline A operated through a new mechanism of action with a phenotypic outcome of disrupting membrane integrity.

Published
2014
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38. Natural Product Discovery Using Planes of Principal Component Analysis in R (PoPCAR).

Author

Chanana, Shaurya, Thomas, Chris S., Braun, Doug R., Yanpeng Hou, Wyche, Thomas P., and Bugni, Tim S.

Subjects
BACTERIAL metabolites, NATURAL products, ACTINOBACTERIA, PRINCIPAL components analysis, METABOLOMICS
Abstract

Rediscovery of known natural products hinders the discovery of new, unique scaffolds. Efforts have mostly focused on streamlining the determination of what compounds are known vs. unknown (dereplication), but an alternative strategy is to focus on what is different. Utilizing statistics and assuming that common actinobacterial metabolites are likely known, focus can be shifted away from dereplication and towards discovery. LC-MS-based principal component analysis (PCA) provides a perfect tool to distinguish unique vs. common metabolites, but the variability inherent within natural products leads to datasets that do not fit ideal standards. To simplify the analysis of PCA models, we developed a script that identifies only those masses or molecules that are unique to each strain within a group, thereby greatly reducing the number of data points to be inspected manually. Since the script is written in R, it facilitates integration with other metabolomics workflows and supports automated mass matching to databases such as Antibase. [ABSTRACT FROM AUTHOR]

Published
2017
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39. Evidence that oxidative dephosphorylation by the nonheme Fe( II), α-ketoglutarate: UMP oxygenase occurs by stereospecific hydroxylation.

Author

Goswami, Anwesha, Liu, Xiaodong, Cai, Wenlong, Wyche, Thomas P., Bugni, Tim S., Meurillon, Maïa, Peyrottes, Suzanne, Perigaud, Christian, Nonaka, Koichi, Rohr, Jürgen, and Van Lanen, Steven G.

Subjects
DEPHOSPHORYLATION, GLUTARIC acid, STEREOSPECIFICITY, HYDROXYLATION, OXYGENASES
Abstract

LipL and Cpr19 are nonheme, mononuclear Fe( II)-dependent, α-ketoglutarate (α KG): UMP oxygenases that catalyze the formation of CO2, succinate, phosphate, and uridine-5′-aldehyde, the last of which is a biosynthetic precursor for several nucleoside antibiotics that inhibit bacterial translocase I (MraY). To better understand the chemistry underlying this unusual oxidative dephosphorylation and establish a mechanistic framework for LipL and Cpr19, we report herein the synthesis of two biochemical probes-[1′,3′,4′,5′,5′-2H] UMP and the phosphonate derivative of UMP-and their activity with both enzymes. The results are consistent with a reaction coordinate that proceeds through the loss of one 2H atom of [1′,3′,4′,5′,5′-2H] UMP and stereospecific hydroxylation geminal to the phosphoester to form a cryptic intermediate, (5′ R)-5′-hydroxy- UMP. Thus, these enzyme catalysts can additionally be assigned as UMP hydroxylase-phospholyases. [ABSTRACT FROM AUTHOR]

Published
2017
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40. Forazoline A: Marine‐Derived Polyketide with Antifungal In Vivo Efficacy

Author

Wyche, Thomas P., primary, Piotrowski, Jeff S., additional, Hou, Yanpeng, additional, Braun, Doug, additional, Deshpande, Raamesh, additional, McIlwain, Sean, additional, Ong, Irene M., additional, Myers, Chad L., additional, Guzei, Ilia A., additional, Westler, William M., additional, Andes, David R., additional, and Bugni, Tim S., additional

Published
2014
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43. Microtermolides A and B from termite-associated Streptomyces sp. and structural revision of vinylamycin

Author

Carr, Gavin, Poulsen, Michael, Klassen, Jonathan L., Hou, Yanpeng, Wyche, Thomas P., Bugni, Tim S., Currie, Cameron R., Clardy, Jon, Carr, Gavin, Poulsen, Michael, Klassen, Jonathan L., Hou, Yanpeng, Wyche, Thomas P., Bugni, Tim S., Currie, Cameron R., and Clardy, Jon

Abstract

Microtermolides A (1) and B (2) were isolated from a Streptomyces sp. strain associated with fungus-growing termites. The structures of 1 and 2 were determined by 1D- and 2D-NMR spectroscopy and high-resolution mass spectrometry. Structural elucidation of 1 led to the re-examination of the structure originally proposed for vinylamycin (3). Based on a comparison of predicted and experimental (1)H and (13)C NMR chemical shifts, we propose that vinylamycin's structure be revised from 3 to 4.

Published
2012

45. Structure elucidation of uniformly 13C labeled small molecule natural products.

Author

Reibarkh, Mikhail, Wyche, Thomas P., Saurí, Josep, Bugni, Tim S., Martin, Gary E., and Thomas Williamson, R.

Subjects
*MOLECULAR structure, *SMALL molecules, *NATURAL products, *ENTEROCINS, *NUCLEAR magnetic resonance
Abstract

Utilization of 2H, 13C, and 15N isotopically labeled proteins and peptides is now routine in biomolecular NMRinvestigations. The widespread availability of inexpensive, uniformly 13C enriched glucose now makes it possible to isolate uniformly 13C labeled natural products from microbial fermentation. We now wish to describe an approach for the rapid structural characterization of uniformly 13C labeled natural products that avoids the pitfalls of relying on parameters typically employed in biomolecular NMR studies. [ABSTRACT FROM AUTHOR]

Published
2015
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46. Structure and Biosynthesis of the Antibiotic Bottromycin D

Author

Hou, Yanpeng, primary, Tianero, Ma. Diarey B., additional, Kwan, Jason C., additional, Wyche, Thomas P., additional, Michel, Cole R., additional, Ellis, Gregory A., additional, Vazquez-Rivera, Emmanuel, additional, Braun, Doug R., additional, Rose, Warren E., additional, Schmidt, Eric W., additional, and Bugni, Tim S., additional

Published
2012
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