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Background and objective L-Ornithine phenylacetate is an intravenous formulation of the L-ornithine salt of phenylacetic acid under development for the treatment of hepatic encephalopathy. Very limited clinical data in patients are available, with a phase II study in target patients not designed for dose finding, to support phase III dose selection in a global development program. The objective of the present population pharmacokinetic modeling and simulation was to evaluate dose selection for target patient populations with a low body weight, ethnicity, and hepatic impairment in a global clinical study. Methods A population pharmacokinetic model was developed based on plasma concentrations of L-ornithine, phenylacetic acid, and phenylacetylglutamine data from four clinical trials in healthy subjects and patients with stable cirrhosis or hospitalized adult patients with liver cirrhosis and hepatic encephalopathy. A covariate analysis was conducted to identify source of variability to support dose selection for global clinical development of L-ornithine phenylacetate. Phenylacetylglutamine formation in the pharmacokinetic model also quantified pharmacodynamic effects measured by ammonia removal. Results Body weight and hepatic function were significant covariates determining phenylacetic acid exposure. After accounting for body weight, there was no difference between tested Caucasian and Asian populations in phenylacetic acid exposure. Renal dysfunction significantly reduced phenylacetylglutamine excretion. However, renal impairment had no impact on plasma phenylacetic acid and free ammonia levels. Exploratory modeling suggested that L-ornithine might enhance the removal of ammonia. Conclusions With a flat dosing algorithm, special consideration must be given to patients with a small body size (i.e., body weight ≤ 50 kg) and severe hepatic impairment.

Phytohormones play key roles in many aspects of plant growth and development, as well as in resistance to abiotic stresses. The presence of heavy metal limits phytohormone endogenous level; however, the application of brassinosteroids (BRs) restores phytohormone homeostasis and reduces unfavorable consequences of heavy metal on plant growth. Therefore, the aim of this study was to (1) broaden previously published analyses/findings to study the effect of 24-epibrassinolide (EBL) and/or lead (Pb) on Acutodesmus obliquus phytohormone level after 5 days of cultivation using LC-QToF-MS quantification technique and (2) extend the total amount of quantified phytohormones in A. obliquus. The study confirmed that exogenous EBL increased the contents of gibberellin A3 (GA3), auxins (AXs) (indole-3-acetic acid, phenylacetic acid), BRs brassinolide, 24-epibrassinolide (EBL), 28-homobrassinolide, castasterone, 24-epicastasterone, typhasterol, cathasterone, 6-deoxotyphasterol, as well as different types of cytokinins (CKs): free bases, ribosides, and conjugates (N- and O-glucosides). On the other hand, treatment with Pb had an opposite effect on BRs, GA3, AXs, and free bases, as well as ribosides of CKs. The abscisic acid (ABA) level decreased under EBL treatment but increased in response to Pb stress. The level of N-glucosides, as well as O-glucosides of CKs, also significantly increased in response to Pb alone. Interestingly, the co-application of EBL and Pb led to an increase in BRs, GA3, AXs, and CKs content in the algae. Principal component analysis revealed that based on treatments, increase of GA3, BRs, and AXs was found to be in the following order: 1 μM EBL > 0.01 μM Pb + 1 μM EBL > 500 μM Pb + 1 μM EBL > control > 0.01 μM Pb > 500 μM Pb. Moreover, very strong significant linear relations between almost all studied AXs and BRs were noted. Summarizing, this research did not only allow to detect the occurrence of ABA, GA3, AXs, BRs, and CKs in A. obliquus for the first time but also to study the combined action of EBL and Pb, as well as compare it with treatment alone.

A simple, efficient and environmentally benign method has been discussed for the synthesis of aldehydes and ketones by the oxidative decarboxylation of phenylacetic acid under ligand free condition using simple, efficient, preparatively easy, magnetically recoverable and low cost spinel CuFe2O4 nanoparticles. The catalyst was characterised using powder-XRD, FTIR, FE-SEM, EDX, VSM and HRTEM. The recyclability was examined and the results showed that the catalyst remained almost equally active up to five consecutive cycles. Spinel Structured Copper Ferrite is a very efficient nano catalyst for Oxidative decarboxylation of Phenyl acetic acids and can be reused up to five cycles without significant loss in catalytic activity.

Gluconobacter oxydans can be used as a whole-cell biocatalyst in many industrial processes focused on production of carbonyl and carboxylic compounds by oxidation of respective alcohols. However, high biocatalyst production costs limit its widespread industrial application. Therefore, the influence of Gluconobacter oxydans cultivation conditions on cell growth and the activity in biooxidation of 2-phenylethanol to phenylacetaldehyde and phenylacetic acid was investigated using batch and fed-batch cultivation cultures. The maximum total activity (given by the product of specific activity of cells and biomass concentration) was obtained by batch cultivation in a medium containing 25 g/L glycerol, at pH 4.5 and 20% oxygen saturation. In a fed-batch culture the best biomass growth was obtained with the feeding medium containing 125 g/L glycerol at a flow rate of 0.02 L/h per 0.5 L of starting culture volume. Although the final biomass concentration was around two times higher, the specific biotransformation activity of cells was only around 20% compared to the biocatalyst prepared by batch culture.

Two new coordination polymers, namely {[Cu(oba)(bpb)0.5](DMF)2}n [1, H2oba = 4,4′-oxybis(benzoic acid), bpb = 1,4-di(pyridin-4-yl)benzene] and {[Zn7(TPA)6(F)4(H2O)6](NO3)4(DMF)3}n (2, Htpa = 4-(1,2,4-triazol-4-yl)phenylacetic acid, DMF = N,N′-dimethylformamide) have been successfully constructed under solvothermal conditions. The in vitro anti-cancer activities of compounds 1 and 2 were evaluated on cancer cells in this study. The CCK-8 assay indicated both compounds 1 and 2 have excellent anti-cancer ability, but the activity of compound 1 is much stronger than compound 2. And the Annexin V-FITC/PI assay revealed that compounds exert anti-cancer effect via inducing cells apoptosis. Then, the further ROS assay revealed that the compound could induce human gastric cancer cells AGS apoptosis by up-regulating the ROS related genes and increasing the generation of ROS.

Several new N-containing epiandrosterone derivatives modified by phenylacetic acid chloride were synthesized for biological activity studies. Compounds with antiviral activity were discovered among them and 3β-hydroxy-1'-aryl-3'-methyl-5'-androstano[17,16-d]pyrazolines prepared by us earlier.

To investigate the antipyretic mechanism of Herba Ephedrae (Eph)-Ramulus Cinnamomi (RC) herb pair on yeast-induced pyrexia in rats. Totally 30 qualified male SD rats were randomly assigned to the normal control (NC) group, the pyrexia model (model) group, the Eph, RC and Eph-RC treatment groups by a random digital table, 6 rats in each group. Each rat received a 20% aqueous suspension of yeast (10 mL/kg) except the NC group. The 3 treatment groups were administered 8.1, 5.4 and 13.5 g/kg Eph, RC and Eph-RC respectively at 5 and 12 h after yeast injection, the NC group and the model groups were administered equal volume of distilled water. Rectal temperatures were measured at 0, 6, 8, 10, 12, 15, 18, 24 and 30 h and urine was collected prior to yeast injection and at 6, 10, 18, 24, 30, and 36 h after yeast injection. Then urine metabolomic profiling by gas chromatography tandem mass spectrometry, coupled with multivariate statistical analysis and pattern recognition techniques were used to explore the antipyretic effects of Eph-RC. Partial least squares discriminate analysis was used to analyze the metabolomics dataset including classification and regression in metabolomics plot profiling. Compared with the NC group, rectal temperatures were significantly higher in the model group (P

This study aimed at developing an efficient biotransformation process for phenylacetic acid production from phenylacetonitrile by using recombinant Escherichia coli M15 harboring a double mutant MG nitrilase (I113M/Y199G) from Burkholderia cenocepacia J2315. A yield of 2310 U/mL nitrilase was obtained by fermentation after the optimization of cultivation conditions, with a specific activity of 64 U/mg dcw. The MG nitrilase showed high substrate tolerance and completely hydrolyzed 100 mM phenylacetonitrile in 30 min under optimal conditions. To alleviate substrate inhibition, periodic or continuous batch-feeding of substrate was used during the biotransformation. Up to 164 g/L substrate was completely hydrolyzed in 9 h with continuous batch-feeding using resting cells, corresponding to 400 U/mL of nitrilase activity, and leading to production of 163.4 g/L phenylacetic acid. The hydrolysis process has potential application for phenylacetic acid production on a large scale.

Phenylacetic acid can be produced from 2-phenylethanol by selective oxidation. This process can be performed using Gluconobacter oxydans immobilized in LentiKats®, polyvinyl alcohol particles with lenticular shape. The biotransformation took place at non-growth conditions in an airlift bioreactor. The goal of this work was to examine the impact of the particles on the hydrodynamics and volumetric mass transfer coefficient for oxygen in the airlift reactor and to describe the activity of the immobilized biomass in such systems. For this purpose, the influence of aeration and 2-phenylethanol concentration on the activity of biomass was examined. Also, the effects of long-term storage of immobilized biomass, long duration of fermentation and repeated use of biomass on the rate of phenylacetic acid production were tested. The results were compared with the phenylacetic acid production by free cells of Gluconobacter oxydans. The results show that aeration of the airlift reactor has only a minor effect on the phenylacetic acid production for immobilized biomass but a significant one for free cells; however, the impact of 2-phenylethanol concentration on the production was notable for both forms of biocatalyst depending on the biomass concentration. Production ability of free cells was ten times higher than that of immobilized cells, but the production time was only a quarter of that of immobilized cells.

N-Methylpyridinium esters derivatives of 2-methylbenzothiazole hemicyanine dyes photoinitiators/photosensitizers derived from N-propyl-3-[N-2-methylbenzothiazolo]-4-pyridyno phenylacetic acid ester diiodide and N-propyl-3-[N-2-me]thylbenzothiazolo]-4-pyridino diphenylacetic acid ester diiodide were synthesized and proposed as new photoinitiators of polymerization of 2-ethyl-(2-hydroxymethyl)-1,3-propanediol triacrylate under argon laser exposure at 514 nm. These compounds exhibit a strong absorption around 520 nm. The dye/borate salt, dye/borate salt/N-methoxypyridinium salt, dye/borate salt/diphenyliodonium salt, and dye/borate salt/1,3,5-triazine derivative combinations are very efficient in initiating of radical photopolymerization of triacrylate. Excellent polymerization profiles were obtained. The effect of both sensitizer and co-initiator structure on the ability to initiate of free radical polymerization of photoinitiating systems was also presented. The mechanism was discussed for different multicomponent initiating systems. Graphical Abstract Two-cationic 2-methylbenzothiazole derivatives as green light absorbed sensitizers in initiation of free radical polymerization.

Phenylacetic acid (PAA) is a fine chemical with a high industrial demand for its widespread uses. Whereas, microorganic synthesis of PAA is impeded by the formation of by-product phenethyl alcohol due to quick, endogenous, and superfluous conversion of aldehydes to their corresponding alcohols, which resulted in less conversation of PAA from aldehydes. In this study, an Escherichia coli K-12 MG1655 strain with reduced aromatic aldehyde reduction (RARE) that does duty for a platform for aromatic aldehyde biosynthesis was used to prompt more PAA biosynthesis. We establish a microbial biosynthetic pathway for PAA production from the simple substrate phenylalanine in E. coli with heterologous coexpression of aminotransferase (ARO8), keto acid decarboxylase (KDC) and aldehyde dehydrogenase H (AldH) gene. It was found that PAA transformation yield was up to ~94% from phenylalanine in E. coli and there was no by-product phenethyl alcohol was detected. Our results reveal the high efficiency of the RARE strain for production of PAA and indicate the potential industrial applicability of this microbial platform for PAA biosynthesis.

Background Lignin is the most abundant aromatic biopolymer in the biosphere and it comprises up to 30% of plant biomass. Although lignin is the most recalcitrant component of the plant cell wall, still there are microorganisms able to decompose it or degrade it. Fungi are recognized as the most widely used microbes for lignin degradation. However, bacteria have also been known to be able to utilize lignin as a carbon or energy source. Bacillus ligniniphilus L1 was selected in this study due to its capability to utilize alkaline lignin as a single carbon or energy source and its excellent ability to survive in extreme environments. Results To investigate the aromatic metabolites of strain L1 decomposing alkaline lignin, GC–MS analysis was performed and fifteen single phenol ring aromatic compounds were identified. The dominant absorption peak included phenylacetic acid, 4-hydroxy-benzoicacid, and vanillic acid with the highest proportion of metabolites resulting in 42%. Comparison proteomic analysis was carried out for further study showed that approximately 1447 kinds of proteins were produced, 141 of which were at least twofold up-regulated with alkaline lignin as the single carbon source. The up-regulated proteins contents different categories in the biological functions of protein including lignin degradation, ABC transport system, environmental response factors, protein synthesis, assembly, etc. Conclusions GC–MS analysis showed that alkaline lignin degradation of strain L1 produced 15 kinds of aromatic compounds. Comparison proteomic data and metabolic analysis showed that to ensure the degradation of lignin and growth of strain L1, multiple aspects of cells metabolism including transporter, environmental response factors, and protein synthesis were enhanced. Based on genome and proteomic analysis, at least four kinds of lignin degradation pathway might be present in strain L1, including a Gentisate pathway, the benzoic acid pathway and the β-ketoadipate pathway. The study provides an important basis for lignin degradation by bacteria. Electronic supplementary material The online version of this article (doi:10.1186/s13068-017-0735-y) contains supplementary material, which is available to authorized users.

Eight metal–organic complexes were synthesized, characterized and evaluated as catalysts for the synthesis of phenylacetic acid. After tests on catalytic activity and catalyst recovery, two Co(II) complexes were proved to be good catalysts in the carbonylation reaction for their enhanced thermal stability and easy recovery from the reaction mixture. The novel catalysts show broad application prospects as they could be used in both homogeneous and two-phase catalytic systems. The catalytic stability of the complexes was also studied by performing consecutive batch runs with the same catalyst sample. The yield was reduced by 2 % first, then by 5 %. After the third batch, it was observed that the phenylacetic acid yield was reduced by less than 10 %, which indicated a high catalytic stability. Orthogonal tests were carried out to optimize experimental conditions. Moreover, the possible mechanism of the catalyzed carbonylation reaction was proposed. In the catalytic cycle, the cobalt complexes are first coordinated by carbon monoxide, and then are attacked by the electrophilic benzyl chloride, react with carbon monoxide afterwards, finally obtain the phenylacetic acid salt under alkaline conditions. During the catalytic cycle, the catalyzed carbonylation reaction has three transition states as carbonyl cobalt complexes, benzyl cobalt complexes and benzyl carbonyl cobalt complexes.

Bamboo varieties are very difficult to improve by traditional breeding methods. Here, we established an efficient plant-regeneration system for Dendrocalamus latiflorus (tropical giant bamboo) by anther culture. Culture conditions, especially the plant growth regulators required for callus induction and shoot differentiation, were optimized by orthogonal design. M8 medium supplemented with 5.37 μΜ α-naphthaleneacetic acid (NAA), 1.33 μM N 6 -benzyladenine (BA), 110.17 μM phenylacetic acid (PAA), and a pretreatment time of 3 d produced the highest rate (5.08 ± 0.61%) of callus induction. The maximum shoot differentiation rate reached 28.3 ± 4.29% in M8 medium supplemented with 2.32 μM kinetin (KT), 8.89 μM BA, 1.08 μM NAA, and 110.17 μM PAA. The results of the ploidy level test showed that most of the regenerated plants were dodecaploid (96/100), a few were hexaploid (3/100), and one was triploid (1/100). The average chlorophyll content of dodecaploid lines was significantly higher than that of hexaploid lines. The present study provides an innovative method for bamboo ploidy breeding and a useful method for genetic improvement.

A series of novel N-arylpyrazole derivatives, 5a–5i, were achieved from substituted phenylacetic acid via Vilsmeier–Haack reaction, hydrolysis, condensation, and aromatic substitution reaction. Their chemical structures were confirmed by 1H NMR, 13C NMR, FTIR, HRMS, and elemental analysis. The newly synthesized compounds were tested for their in vitro cytotoxic activity against Bel-7402, KB, HL-60, and BGC-823 cell lines and found to possess moderate activity.

A series of novel N-arylpyrazole derivatives, 5a–5i, were achieved from substituted phenylacetic acid via Vilsmeier–Haack reaction, hydrolysis, condensation, and aromatic substitution reaction. Their chemical structures were confirmed by 1H NMR, 13C NMR, FTIR, HRMS, and elemental analysis. The newly synthesized compounds were tested for their in vitro cytotoxic activity against Bel-7402, KB, HL-60, and BGC-823 cell lines and found to possess moderate activity.

A series of new hydantoin compounds was synthesized with 3-bromo phenylacetic acid and 3,4-dimethylbromobenzene as starting material, 7-bromo-2-tetralone and 2-bromo-5,6,8,9-tetrahydro-7-benzocyclo-heptenone as intermediate and Ullmann reaction, Suzuki reaction and Bucherer-Berg’s reaction as key steps. The structures of the key intermediate and target compounds were confirmed by 1H NMR, 13C NMR, IR and MS. Bioactivity research showed that target compounds 6a, 6c, 6d, 6e and 15i had significant antitussive effect on the ammonia-induced cough of mice.

Cardiovascular disease (CVD) is prevalent in patients with chronic kidney disease (CKD). In hemodialysis (HD) patients, some protein-bound uremic toxins are considered to be associated with CVD. However, it is not yet known which uremic toxins are important in terms of endothelial toxicity. Serum samples were obtained from 45 HD patients before and after HD. Total and free serum concentrations of indoxyl sulfate, indoxyl glucuronide, indoleacetic acid, p-cresyl sulfate, p-cresyl glucuronide, phenyl sulfate, phenyl glucuronide, phenylacetic acid, phenylacetyl glutamine, hippuric acid, 4-ethylphenyl sulfate, and 3-carboxy-4-methyl-5-propyl-2-furanpropionic acid (CMPF) were simultaneously measured by liquid chromatography/electrospray ionization–mass spectrometry/mass spectrometry (LC/ESI-MS/MS). The effects of these solutes at their pre-HD mean and maximum serum concentrations on reactive oxygen species (ROS) production in human umbilical vein endothelial cells (HUVEC) were measured with a ROS probe. Serum levels of 11 of the solutes (all except 4-ethylphenyl sulfate) were significantly increased in HD patients compared to healthy subjects. All 12 solutes showed changes in their protein-binding ratios. In particular, indoxyl sulfate, p-cresyl sulfate, CMPF, and 4-ethylphenyl sulfate showed high protein-binding ratios (>95 %) and low reduction rates by HD (

In the last step of penicillin biosynthesis, acyl-CoA:isopenicillin N acyltransferase (IAT) (E.C. 2.3.1.164) catalyzes the conversion of isopenicillin N (IPN) to penicillin G. IAT substitutes the α-aminoadipic acid side chain of IPN by a phenylacetic acid phenolate group (from phenylacetyl-CoA). Having a three-dimensional (3D) structure of IAT helps to determine the steps involved in side chain exchange by identifying the atomic details of substrate recognition. We predicted the IAT 3-D structure (α- and β-subunits), as well as the manner of IPN and phenylacetyl-CoA bind to the mature enzyme (β-subunit). The 3D IAT prediction was achieved by homology modeling and molecular docking in different snapshots, and refined by molecular dynamic simulations. Our model can reasonably interpret the results of a number of experiments, where key residues for IAT processing as well as strictly conserved residues most probably involved with enzymatic activity were mutated. Based on the results of docking studies, energies associated with the complexes, and binding constants calculated, we identified a site located in the region generated by β1, β2 and β5 strands, which forms part of the central structure of β-subunit, as the potential binding site of IPN. The site comprises the amino acid residues Cys103, Asp121, Phe122, Phe123, Ala168, Leu169, His170, Gln172, Phe212, Arg241, Leu262, Asp264, Arg302, Ser309, and Arg310. Through hydrogen bonds, the IPN binding site establishes interactions with Cys103, Leu169, Gln172, Asp264 and Arg310. Our model is also validated by a recently revealed crystal structure of the mature enzyme.

1H NMR metabolic profiles of urine from sheep exposed to prenatal nutritional restriction (n = 19) and a control group with normal prenatal nutritional requirements (n = 19), followed by either conventional (n = 10 + 10) or high carbohydrate high fat postnatal diet (n = 9 + 9), were studied. Urine was sampled from 2, 6, 19 and 24-month-old animals receiving differential dietary treatments during the first 6 months and the same normal diet later. Principal component analysis of 1H NMR spectra (n = 164) showed a V-shaped metabolic trajectory as a function of age and diet, starting with urines with a high amount of glucose, indicative of monogastric-like metabolism, and exhibiting concomitant increase of metabolites related to rumen microflora (mainly glycine conjugates of benzoic and phenylacetic acid) as the ruminal metabolism developed. Urines from young (2-month-old) animals exposed to prenatal undernutrition followed by normal postnatal diet showed metabolic patters that are ahead in time on the metabolic trajectory relative to the prenatal control group. No long-term effects of fetal undernutrition, alone or in combination with postnatal hypernutrition were observed.

This work describes the degradation of phenylalanine and tryptophane catalysed by their complexes with Fe(II), Co(II), and Cu(II). The influences of the central atom and of the reaction conditions on the degradation of the amino acids were observed. The necessary condition of the degradation is the possibility of a redox reaction on the central atom between M(II) and M(III). Moreover, the coordination sphere of the central cation of the transition metal must not be sterically shielded. The necessary conditions are fulfilled only in the Fe(II) complexes. The degradation is strictly anaerobic because due to the influence of oxygen, an irreversible oxidation of Fe(II) to Fe(III) proceeds. This reaction results in 5-hydroxy-1H-indol instead of the mixture of the degradation products, such as benzaldehyde, phenylacetaldehyde, and phenylacetic acid. The influence of the temperature on the catabolism is very important because the reaction accelerates with temperature increase. The phenylalanine anion acts as a reducing agent, and Fe(II) is spontaneously reduced to Fe(0).

The effects of β-lactam antibiotics (penicillin, carbenicillin and cefotaxime), cytokinins, and auxins including phenylacetic acid, a β-lactam breakdown product, were evaluated during in vitro shoot morphogenesis in two hybrid aspens; P. tremuloides × P. tremula (XTTa) and P. x canescens × P. grandidentata (XCaG). Although different callus and shoot induction media were used for both hybrids, the β-lactams often engendered similar responses. At concentrations of 1,000 mg l−1, carbenicillin adversely impacted shoot elongation and, to a lesser degree, shoot regeneration. Cefotaxime enhanced caulogenesis for all of the concentrations evaluated (125–500 mg l−1) especially when the cytokinin thidiazuron was used for shoot induction. The shoots formed faster and in greater numbers; and the improvements were significant (α = 0.05) for both hybrids. However, hyperhydricity was more problematic when cefotaxime was included in the media. The incidence of shoot hyperhydricity for the XCaG hybrid was more than twice as great for the highest cefotaxime concentration evaluated (500 mg l−1) than for the control (>90% vs. ~40%). Penicillin had an opposite effect. Hyperhydricity frequencies for the XCaG hybrid were lower when the media were supplemented with penicllin and the reductions were statistically significant at concentrations of 500–1,000 mg l−1. The effects of the antibiotics were generally not reproduced by the auxins (0.1–100 μM), including phenylacetic acid, or the other potential β-lactam degradation products evaluated (e.g. phenylmalonic acid, aminopenicillanic acid). The antibiotics may have affected shoot hyperhydicity indirectly via changes in the time course of shoot regeneration.

The heterocyclization of 2-acetyl-3-indolylacetic acid hydrazones and its amides, in contrast to similar derivatives of phenylacetic acid, does not lead to 2,3-dihydro-2-oxo-5-R1-1H-[1,2]diazepino-[4,5-b]indoles but rather to 2-aminoindolo[2,3-c]pyridin-3(2H)-one or azines of 2-acetyl-3-indolyl-acetic acid. 2,3-Dihydro-2-oxo-5-R1-1H-[1,2]diazepino[4,5-b]indoles were obtained by the reaction of 1-alkylaminoacetylindolo[2,3-c]pyrilium perchlorates and of methyl esters of 2-acetyl- and 2-propionyl-3-indolylacetic acid with hydrazine hydrate.

Several (E)- and (Z)-3-styrylchromones were prepared by two different methodologies, the Wittig reaction of chromone-3-carboxaldehyde with benzylic ylides and the Knoevenagel condensation of chromone-3-carboxaldehyde with phenylacetic acids in the presence of potassium tert-butoxide under microwave irradiation. The Knoevenagel reaction followed by a decarboxylation offered an efficient and diastereoselective method for preparing (E)-3-styrylchromones in a shorter reaction time. It was also demonstrated that phenylacetic acid can also be substituted with success by phenylmalonic acid. The stereochemistry of all products was assigned by NMR experiments.

Arthrobacter oxydans CECT386 is a Gram-positive bacterium able to use either phenylacetic acid or phenylacetaldehyde as the sole carbon and energy source for aerobic growth. Genes responsible for the catabolism of these compounds have been located at two chromosomal regions and were organized in one isolated paaN gene and two putative paa operons, one consisting of the paaD, paaF, tetR and prot genes, and one consisting of the paaG, paaH, paaI, paaJ, paaK and paaB genes. The identity of the paaF and paaN genes was supported by functional complementation experiments. A comparison with the paa catabolic genes and/or gene clusters of other bacteria that degrade these aromatic compounds is presented. The results of this study broaden the knowledge regarding the range of metabolic potential of this strain and eventually make it attractive for environmental applications.

With a combination of dichloromethane extraction and analysis by gas chromatography-mass spectrometry (GC-MS), we found 39 compounds (corresponding to 38 GC peaks) in the anogenital gland secretion (AGS) of captive adult giant pandas, Ailuropoda melanoleuca, during the non-mating season. In addition to indole, squalene, and some of the straight-chain fatty acids that had been characterized previously from the AGS of giant pandas, we identified several new compounds such as decenal, two isomers of decadienal, phenylacetic acid, 5-methylhydantoin, hydroquinone, phenylpropanoic acid, and erucic acid. Quantitative comparison of the relative abundances of the 20 main GC peaks revealed that 5-methylhydantoin, indole, and erucic acid are putative female pheromones, whereas squalene and hydroquinone are putative male pheromones. In addition to the presence of a few individual-specific compounds, the relative abundances of most of the 21 constituents varied more among individuals than within individuals. This suggests that individual identity might be coded in both digital and analog form. The chemical composition of different AGS samples from the same pandas consistently displayed a minimum cluster distance, much smaller than that between samples from different individuals in a hierarchical linkage cluster (average linkage) dendrogram. Our results indicate that the AGS might contain an "odor fingerprint." Although putative sex pheromones such as squalene and erucic acid should be assessed further by bioassay, our study suggests that synthetic chemosignals might be useful in modulating the behavior and physiology of giant pandas.

Cladosporium sp. isolate N5 was isolated as a dominant fungus from the healthy conchocelis of Porphyra yezoensis. In the re-infection test, it did not cause any pathogenic symptoms in the alga. Twenty-one cultural conditions were chosen to test its antimicrobial activity in order to obtain the best condition for large-scale fermentation. Phenylacetic acid, p-hydroxyphenylethyl alcohol, and L-beta-phenyllactic acid were isolated from the crude extract as strong antimicrobial compounds and they are the first reported secondary metabolites for the genus Cladosporium. In addition, the Cladosporium sp. produced the reported Porphyra yezoensis growth regulators phenylacetic acid and p-hydroxyphenylacetic acid. No cytotoxicity was found in the brine shrimp lethality test, which indicated that the environmental-friendly Cladosporium sp. could be used as a potential biocontrol agent to protect the alga from pathogens.

Penicillium chrysogenum npe10 (Deltapen; lacking the 56.8-kbp amplified region containing the penicillin gene cluster), complemented with one, two, or three penicillin biosynthetic genes, was used for in vivo studies on transport of benzylpenicillin intermediates. 6-Aminopenicillanic acid (6-APA) was taken up efficiently by P. chrysogenum npe10 unlike exogenous delta(L: -alpha-aminoadipyl)-L: -cysteinyl-D: -valine or isopenicillin N (IPN), which were not taken up or were taken up very poorly. Internalization of exogenous IPN and 6-APA inside peroxisomes was tested by quantifying their peroximal conversion into benzylpenicillin in strains containing only the penDE gene. Exogenous 6-APA was transformed efficiently into benzylpenicillin, whereas IPN was converted very poorly into benzylpenicillin due to its weak uptake. IPN was secreted to the culture medium. IPN secretion decreased when increasing levels of phenylacetic acid were added to the culture medium. The P. chrysogenum membrane permeability to exogenous benzylpenicillin was tested in the npe10 strain. Penicillin is absorbed by the cells by an unknown mechanism, but its intracellular concentration is kept low.

Density data for dilute aqueous solutions of phenylacetic acid, benzene-1, 2-dicarboxylic acid (phtalic acid), benzene-1,2,4-tricarboxylic acid and 1,2,3-trihydroxy- benzene (pyrogallol) are presented together with the partial molar volumes at infinite dilution calculated from the experimental data. The measurements were performed at temperatures from T=298.15 K up to T=373.15 K and at three pressures up to 30 MPa. The data were obtained using a high-temperature, high-pressure flow vibrating-tube densimeter.

The volatile fraction of commercial cocoa powders was isolated using thin-layer high-vacuum distillation (TLHVD) of Soxhlet extracts. Calculated and experimental recovery of the internal standard n-undecanoic acid methylester did agree, and a good reproducibility was found for the procedure. Around 70 volatile compounds were identified and semi-quantified using internal standard-based gas chromatography (GC), coupled GC–mass spectrometry (GC–MS) and GC-olfactometry (GC-O). Dehydromevalonic acid lactone, (R)-(−)-pantolactone and two diastereomer solerols were identified for the first time after purification by micropreparative GC and re-analysis using GC–MS and chiral GC. Strong sensory contributions also came from acetic acid, 2/3-methyl butanoic acid, phenylacetaldehyde, furaneol, dihydroxymaltol, vanillin and phenylacetic acid.

The penicillin G amidase (PGA) activity of a parent strain of E. coli (PCSIR-102) was enhanced by chemical mutagenization with N-methyl-N′-nitro-N-nitrosoguanidine (MNNG). After screening and optimization, a penicillinase deficient mutant (MNNG-37) was isolated and found effective for the production of penicillin G amidase as compared to the parent strain of E. coli (PCSIR-102). Penicillin G amidase activity of MNNG-37 appeared during an early stage of growth, whereas PCSIR-102 did not exhibit PGA activity due to the presence of penicillinase enzyme which inhibits the activity of enzyme PGA. However, MNNG-37 gave a three-fold increase in enzyme activity (231 IU mg−1) as compared to PCSIR-102 (77 IU mg−1) in medium containing 0.15 and 0.1% concentrations of phenylacetic acid, respectively which was added after 6 h of cultivation. The difference in K m values of the enzyme produced by parent strain PCSIR-102 (0.26 mM) and mutant strain MNNG-37 (0.20 mM) is significant (1.3-fold increase in K m value) which may show the superiority of the latter in terms of better enzyme properties.

Zinc complexes of meso-phenyltetrabenzoazaporphyrins were prepared by the reaction of iso-indoline-1,3-diimine with phenylacetic acid in the presence of zinc oxide. Treatment of the products with sulfuric acid gave metal-free compounds.

Lyophilized mycelia of Aspergillus oryzae CBS 102.07, Aspergillus oryzae MIM, Rhizopus oryzae CBS 112.07, Rhizopus oryzae CBS 391.34, Rhizopus oryzae CBS 260.28 and Rhizopus oryzae CBS 328.47 were tested in this study to select the best biocatalysts for ethanol acylation with phenylacetic acid. The mycelium-bound carboxylesterase activity of A. oryzae MIM, which exhibited the best performances, was initially investigated at 50 degrees C, either in 0.1 M phosphate buffer or in n-heptane to catalyse the hydrolysis or the synthesis, respectively, of ethyl phenylacetate. The results in terms of product and substrate concentrations versus time were used to estimate the maximum molar conversions at equilibrium, the equilibrium constants, and the times needed to reach half maximum conversions, thus providing sufficient information about this biotransformation. The values of the apparent equilibrium constants, estimated at 20 degrees CT50 degrees C, were finally used to estimate the thermodynamic parameters of ethanol acylation by this biocatalyst.

Candida antarctica lipase fraction B (CAL-B) showed substrate specificity in the synthesis of esters in hexane involving reactions of short-chain acids having linear (acetic and butyric acids) and branched chain (isovaleric acid) structures, an unsaturated (tiglic acid) fatty acid, and phenylacetic acid with n-butanol and geraniol. The variation in the conversion to the esters was ca. 10%. Similar results were observed in a study of the alcohol specificity of the enzyme for esterification of acetic and butyric acids with four alcohols: n-butyl, isopentyl, 2-phenylethyl, and geraniol. Enantioselectivity of CAL-B in hexane with a range of chiral alpha-substituted or beta-substituted carboxylic acids and n-butyl alcohol was analyzed. The results show that CAL-B can be employed as a robust biocatalyst in esterification reactions due to the high conversions obtained in the synthesis of short-chain flavor esters in an organic solvent, although this enzyme exhibited modest enantioselectivity with chiral short-chain carboxylic acids.

Micromonospora sp. M39 was selected as a producer of antifungal substances. Cell mass and antifungal activity of the organism was dependent on the carbon and nitrogen sources used. A combination of glucose, starch and glycerol as carbon sources at 1%(w/v) and corn steep powder as a nitrogen source at 0.25%(w/v) concentration in basal medium gave a maximum growth of 17.2 PCV/50 ml and in vitro an antifungal activity of 19.0 mm against the rice blast pathogen Pyricularia oryzaeMPO 293. In the selected production medium, optimum antifungal activity of the crude extract of the strain M39 was on day 16 of fermentation at 28 ± 2 °C. The crude extract of the strain M39 was analyzed and characterized by HPLC-DAD-UV–visible spectra. The peaks with a retention time of 4.88 min had a u.v. spectrum identical to that of 2,3-dihydroxybenzoic acid. The peak with a retention time of 6.08 min was confirmed by an automated spectral library search as phenylacetic acid. Two other peaks in the chromatogram were identified as cervinomycin A1 with a retention time at 12.78 min and cervinomycin A2 with a retention time at 13.46 min.

2-Phenylethylamine is an endogenous constituent of human brain and is implicated in cerebral transmission. It is also found in certain foodstuffs and may cause toxic side-effects in susceptible individuals. Metabolism of 2-phenylethylamine to phenylacetaldehyde is catalyzed by monoamine oxidase and the oxidation of the reactive aldehyde to its acid derivative is catalyzed mainly by aldehyde dehydrogenase and perhaps aldehyde oxidase, with xanthine oxidase having minimal transformation. The present investigation examines the metabolism of 2-phenylethylamine to phenylacetaldehyde in liver slices and compares the relative contribution of aldehyde oxidase, xanthine oxidase and aldehyde dehydrogenase activity in the oxidation of phenylacetaldehyde with precision-cut fresh liver slices in the presence/absence of specific inhibitors of each enzyme. In liver slices, phenylacetaldehyde was rapidly converted to phenylacetic acid. Phenylacetic acid was the main metabolite of 2-phenylethylamine, via the intermediate phenylacetaldehyde. Phenylacetic acid formation was completely inhibited by disulfiram (specific inhibitor of aldehyde dehydrogenase), whereas isovanillin (specific inhibitor of aldehyde oxidase) inhibited acid formation to a lesser extent and allopurinol (specific inhibitor of xanthine oxidase) had little or no effect. Therefore, in liver slices, phenylacetaldehyde is rapidly oxidized by aldehyde dehydrogenase and aldehyde oxidase with little or no contribution from xanthine oxidase.

A bacterial strain, B65-1, which showed strong antimicrobial activity, was isolated from Chungkook-Jang, a traditional Korean fermented-soybean food with antimicrobial properties. Based on carbon utilization pattern and partial 16S rRNA sequence analysis, the B65-1 strain was identified as Bacillus licheniformis. An antibiotic compound, active against bacteria and yeast such as Staphylococcus aureus, Escherichia coli, and Candida albicans, was isolated by various chromatographic procedures from culture filtrates of B. licheniformis B65-1. The purified antibiotic was identified to be phenylacetic acid, with the molecular formula C(8)H(8)O(2) by analyses of EI-MS and NMR. The phenylacetic acid was detected in fermented soybean made with the strain B65-1 as a starter, but was not present in extracts of nonfermented soybean. Our results indicated that the phenylacetic acid produced by B. licheniformis during fermentation of soybean is one of the main compounds of antimicrobial activity of Chungkook-Jang.

A reaction of phthalimide with phenylacetic acid in the presence of zinc oxide furnished 3-oxoisoindolenyl-3'-oxoisoindolinylidene-1,1'-benzylidine which at heating with 1-naphthylacetic acid in the presence of zinc oxide provided zinc meso-trans-diphenyldi(1-naphthyl)tetrabenzoporphin complex. Proceeding from this compound a meso-trans-diphenyldi(1-naphthyl)tetrabenzoporphin was prepared. The spectral characteristics of compounds obtained were studied.

A bacterial strain producing a beta-lactam antibiotic acylase, able to hydrolyze ampicillin to 6-aminopenicillanic acid more efficiently than penicillin G, was isolated from soil and characterized. The isolate was identified as Achromobacter sp. using the phenotypic characteristics, composition of cellular fatty acids and 16S rRNA gene sequence. The enzyme synthesis was fully induced by phenylacetic acid (PAA) at a concentration of 2 g l(-1). PAA at concentrations up to 12 g l(-1) had no negative effect on the specific activity of acylase and biomass production, but slowed down the specific growth rate. Benzoic or 4-hydroxyphenylacetic acids can also induce synthesis of the enzyme. The inducers were metabolized in all cases. Acylase activity in cell-free extracts was determined with various substrates; ampicillin, cephalexin and amoxicillin were hydrolyzed 1.5- and 2-times faster than penicillin G. A high stability of acylase activity was observed over a wide range of pH (5.0-8.5) and at temperatures above 55 degrees C.

We reported previously that a 3.6-kb double-stranded RNA, designated as M2, is associated with hypovirulence in the Rhizoctonia solani isolate Rhs 1A1 and proposed that the M2-encoded putative polypeptide A (pA) might interfere with the regulation of the quinate and shikimate pathways. In this study, Western blot analysis showed that a protein band of the predicted size (83 kDa) binds antibodies specific to a pA epitope and is detectable in M2-containing but not in M2-lacking cultures. A mRNA, associated with Rhs 1A1 polysomes immunoprecipitated with anti-pA antibodies, has a sequence basically identical to that of the sense-strand of M2. The normally inducible quinate pathway was constitutively expressed, whereas the shikimate pathway was down-regulated in the M2-containing, hypovirulent Rhs 1A1. Finally, the relative concentration of phenylalanine, precursor of the virulence determinant phenylacetic acid, was correlated with the degree of pathogenicity in the virulent Rhs 1AP but not in the hypovirulent Rhs 1A1.

A broad-host range metabolic cassette has been designed that, under the control of the Ptac promoter, expresses the styABCD catabolic genes from Pseudomonas sp. Y2, which are responsible for the transformation of styrene into phenylacetic acid (styrene upper pathway). This novel cassette confers to phenylacetic acid-degrading bacteria the ability to grow efficiently on styrene as the sole carbon and energy source. By combining both the sty cassette and the archetypal pWW0 TOL plasmid into the well-known Pseudomonas putida F1 aromatic biodegrader, we have constructed a novel derivative strain that shows one of the largest degradative potentials so far described for aromatic hydrocarbons, because it is able to use BTEX compounds (benzene, toluene, ethylbenzene and xylenes) and styrene as a source of carbon and energy. Furthermore, the sty cassette was engineered within a mini-transposon and endowed with a gene containment system, based on the toxic effect of the colicin E3 RNase, to reduce its lateral spread to other hosts. This contained cassette lacks defined transcriptional regulatory signals and, thus, it becomes an alternative strategy to select recombinant strains that efficiently express the desired phenotype from housekeeping regulatory elements.

A Bacillus sp. producing a high level of intracellular penicillin G acylase (PAC) was isolated. The PAC production in this strain was induced by phenylacetic acid. Various carbon and nitrogen sources were evaluated for their effect on growth and PAC production at 28 °C and pH 7.0. Cells grown in medium supplemented with sucrose as carbon source and tryptone as nitrogen source produced maximum activity of 6.45 and 8.92 U mg−1, respectively. Maximum concentration of PAC (10.1 Umg−1) was produced by the cells grown in the medium containing sucrose and tryptone, which was twofold higher than the production in basal medium.

The de novo formation of organochlorines was observed in a municipalsewage treatment plant. Due to this formation, the amount of organically boundhalogens (AOX) increased 15-fold inside the sewage treatment plant. Per day,more than 6 kg of organically-bound chlorine were produced. Thisformation is not based on a metabolism of present organochlorines, it is a denovo formation out of inorganic chloride and organic substrates. The AOXtriggerconcentration in sewage sludge in Germany is 500 mgkg−1 and was sometimes exceeded by a factor of 10. Noknown anthropogenic organohalogens were found which could explain the elevatedAOX concentrations. Instead many chlorinated compounds could be identifiedwhichwere not known to be of anthropogenic origin. The compound with the highestconcentration was the 3,4-dichlorophenylacetic acid (3,4-CPAc). In one case,more than 1 g kg−1 of this compound was detected.A slaughterhouse that emits phenylacetic acid is probably the origin of thatformation. In model experiments phenylacetic acid was chlorinated with HOCl butchlorinated phenylacetic acids other than 3,4-CPAc were found. Therefore it canbe excluded that the chlorination in the sewage treatment plant takes place byan abiotic reaction with hypochlorite that might have been introduced there. Weassume that the occurring microorganisms are responsible for the de novoformation in the sewage treatment plant. The obtained knowledge could also beuseful to understand natural chlorination processes.

The aerobic metabolism of phenylacetic acid (PA) and 4-hydroxyphenylacetic acid (4-OHPA) was investigated in the beta-proteobacterium Azoarcus evansii. Evidence for the existence of two independent catabolic pathways for PA and 4-OHPA is presented. 4-OHPA metabolism involves the formation of 2,5-dihydroxyphenylacetate (homogentisate) and maleylacetoacetate catalyzed by specifically induced 4-OHPA 1-monooxygenase and homogentisate 1,2-dioxygenase. The metabolism of PA starts by its activation to phenylacetyl-CoA (PA-CoA) via an aerobically induced phenylacetate-coenzyme A ligase. Phenylalanine (Phe) aerobic metabolism in this bacterium proceeds also via PA and PA-CoA. Whole cells of A. evansii transformed [1-(14)C]PA to (14)C-phenylacetyl-CoA and subsequently to a number of unknown labeled products, which were also observed in PA-degrading bacteria from different phylogenetic groups, i.e. Escherichia coli, Rhodopseudomonas palustrisand Bacillus stearothermophilus. A chromosomal region from A. evansiiof 11.5 kb containing a cluster of 11 phenylacetic acid catabolic ( paa) genes ( paaYZGHIKABCDE) was sequenced and characterized. The derived gene products were similar to the characterized putative gene products involved in PA catabolism in E. coli and Pseudomonas putida and to other putative PA catabolic gene products of diverse bacteria. RT-PCR analysis of the paa genes of A. evansiigrowing aerobically with PA showed a probable organization of the paa genes in three operons. The similarity of the PA metabolic products pattern and of gene sequences suggests a common aerobic bacterial PA pathway.

Volatiles collections and cuticular extracts of the wheat stem sawfly, Cephus cinctus Norton (Hymenoptera: Cephidae), were analyzed by coupled gas chromatographic–electroantennographic detection (GC-EAD) in order to detect possible pheromone components of this species. Volatiles collections from male and female sawflies contained the same 13 GC-EAD-active compounds that stimulated both male and female antennae. GC-EAD-active compounds were identified by mass spectrometry, and the identities were verified by acquiring or synthesizing authentic standards with identical GC retention times and mass spectra. 9-Acetyloxynonanal gave the strongest EAD response. Additional GC-EAD-active compounds included 13-acetyloxytridecanal, aldehydes with 9–16 carbon chain lengths, acids with 8–10 carbon chain lengths, and phenylacetic acid. The last was instantly detectable by human nose when several males were allowed to interact, but not from isolated insects. On a per-insect basis, grouped males overall released higher amounts of the GC-EAD-active compounds than grouped females. Notable quantitative differences between the sexes were relatively higher amounts of 9-acetyloxynonanal, phenylacetic acid, and tetradecanal from males and hexadecanal from females. In the absence of an absolute, qualitative difference between sexes, these relative differences might be important for sex recognition. Field bioassay demonstrated the attractiveness of 9-acetyloxynonanal for male and female C. cinctus. The major compounds of male and female cuticular extracts showed no GC-EAD activity, but ozonolysis of extracts gave dramatically increased amounts of GC-EAD-active material. Hence, double-bond-containing cuticular compounds are suggested as precursors of the aldehydic pheromone components.

Magnesium complexes of highly soluble meso-phenyl-substituted tetrabenzoazaporphins were prepared from 1,3-diiminoisoindoline and phenylacetic acid in the presence of magnesium oxide. Some physicochemical and spectral properties of the compounds were investigated.

Saussurea superba Anthony belongs to the Compositae family and is one of the major medicinal plants in China. Its roots have long been used as folk medicine to treat influenza, pharyngeal swelling, measles, urticaria, and food poisoning [1]. The present research deals with the isolation and elucidation of compounds 1–20 from the whole plant of S. superba. The compounds isolated were identified as follows: stigmast-1,4-dien-3-one (1) [2], stigmast-4-en-3-one (2) [3], 6 -hydroxystigmast-4-en-3-one (3) [3], -sitosterol (4) [3], sitosterol-5-en-3 ,7 -diol (5) [3], 3 -hydroxystigmast-5-en7-one (6) [3, 4], 5,6 -epoxy-5 -sitostan-3 -ol (7) [5], 5,6 -epoxy-5 -sitostan-3 -ol (8) [12], 5 ,8 -epidioxy-24(S)methylcholesterol-6,22-dien-3 -ol (9) [6], lupeol (10) [7, 8], -amyrin (11) [9], 3 -hydroxy-urs-12-en-11-one (12) [10], luteolin (13) [11], luteolin-3 -O-D-glucopyranoside (14) [12], umbelliferone (15) [13], scopoletin (16) [14], skimmin (17) [13, 15], scopolin (18) [13, 15], 2-hydroxy-4-acetoanisole (19) [16], and phenylacetic acid (20) [17]. These compounds were characterized by spectral data and comparison with those reported in previous work. Plant Materials. The whole plant of Saussurea superba was collected in Huzhu county, Qinghai province, P. R. China, in August 2002. It was identified by Dr. Huan-Yang Qi. The voucher specimens (2002002) were deposited in the Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, P. R. China. Extract, Isolation, and Purification. The dried plant material (2.0 kg) was powdered and extracted with 95% of industrial ethanol at 60 C for 24 h and then evaporated. The residue (120 g) was mixed with 500 mL water and extracted with petroleum ether, EtOAc, and n-butanol, respectively, to yield three parts (A, B, and C). Part A (30 g) was chromatographed on a silica gel column, eluting with petroleum ether (60–90 C)–acetone (v/v = 30:1, 20:1, 15:1, 10:1, 5:1, 3:1, 1:1, each about 3.0 L), to give four fractions (A1–A4) after concentration at reduced pressure. Fraction A1 was applied to a silica gel column, eluting with petroleum ether–EtOAc (v/v, from 30:1 to 25:1), to yield compounds 19 (600 mg), 4 (168 mg), and 10 (20 mg). Fraction A2 was eluted on a silica gel column with CHCl3–acetone (40:1) to give compounds 1 (7 mg ) and 3 (5 mg) after purified by pre-TLC. Compounds 2 (27 mg) and 11 (4 mg) were subsequently crystallized from fraction A3, eluting with CHCl3–acetone (20:1). Fraction A4 was eluted on a silica gel column with CHCl3–EtOAc (15:1) to afford a crude mixture of 5, 9, and 6 (10 mg) and 12 (3 mg). The mixture was processed by pre-TLC to give crystals 5 (2 mg) and 9 (7 mg). Part B (20 g) was eluted on a silica gel column with petroleum ether–EtOAc (6:1) and petroleum ether–acetone (v/v, from 10:1 to 7:1) to afford compounds 13 (14 mg), 15 (1 g), and 16 (14 mg), and then by pre-TLC (petroleum ether–EtOAc, 8:1) to give white solids 20 (120 mg), 7 (2 mg), and 8 (2 mg). Part C (54 g) was applied to a silica gel column, eluting with a CHCl3–CH3OH gradient to yield 14 (272 mg), 17 (19 mg), and 18 (7 g), respectively.

Benzylpenicillin filtered broths purified by ultrafiltration and fermented broths clarified by ultrafiltration and afterwards concentrated by reverse osmosis were used directly for enzymatic conversion of benzylpenicillin to 6-aminopenicillanic acid and phenylacetic acid by immobilised penicillin G acylase or amidase. It was concluded that, when the ultrafiltration operation retained 100% of protein, the concentrates from reverse osmosis could be successfully directly fed to the enzymatic reactor, giving high enzymatic conversion yield of benzylpenicillin to 6-aminopenicillanic acid.

Di- and triesters of saccharose with aromatic acids are synthesized by transesterification of the methyl esters of the corresponding acids with saccharose. The structures of the resulting compounds are confirmed by IR spectroscopy, PMR, and 13 C NMR.

Penicillin G (Pen-G) was hydrolyzed to 6-aminopenicillanic acid (6-APA) and phenylacetic acid (PAA) in a chromatographic reactor-separator using the mixture of immobilized Escherichia coli cells and a macroporous adsorbent as stationary phase and a phosphate buffer of pH 7.8 as eluant. Pen-G conversion of 98% was observed without adjustment of the eluant pH due to the effective separation of 6-APA from Pen-G and PAA. At a sample load of 600 mg Pen-G, the volume overload gave higher Pen-G conversion (86%) than the mass overload (68%), while their difference in product resolution (0.9 and 1.0, respectively) was insignificant.