Catabolism of 2,4,5-trimethyoxybenzoic acid and 3-methoxycrotonic acid

4-Methoxygentisic acid was an intermediate formed when Arthrobacter degraded, 2,4,5-trimethoxybenzoic acid. Isolates of Pseudomonas and Arthrobacter from soil grew at the expense of 3-methoxycrotonic acid. Evidence is presented that enzymatic hydration, with elimination of methanol, accounted for replacement of the methoxyl group of 3-methoxycrotonic acid and also of one methoxyl group of 2,4,5-trimethoxybenzoic acid.     

Identification of oxindole-3-acetic acid,and metabolic conversion of indole-3-acetic acid to oxindole-3-acetic acid in Pinus sylvestris seeds

Oxindole-3-acetic acid (OxIAA) has been identified in germinating seeds of Scots pine (Pinus sylvestris) using gas chromatography-mass spectrometry. Seeds germinated for 5 d contained 2.7 ng OxIAA·g^-1 (dry weight) whereas ungerminated seeds contained 0.2 ng·g^-1. Isotopically labelled OxIAA was formed in seeds incubated with [1-¹⁴C]-, [2-¹⁴C]- or [²H₅]indole-3-acetic acid.Abbreviations DDC sodium diethyldithiocarbamate - GC gas chromatography - HPLC high-performance liquid chromatography - IAA indole-3-acetic acid - MS mass spectrometry - OxIAA oxindole-3-acetic acid - PVP polyvinylpyrrolidone - TMS trimethylsilyl     

Failure of 3-hydroxy-3-phenylpropanoic acid and cinnamic acid to serve as precursors of tropic acid in Datura innoxia

Datura innoxia plants were fed the R- and S-isomers of [3-¹⁴C]-3-hydroxy-3-phenylpropanoic acid, and [3-¹⁴C]cinnamic acid along with dl-[4-³H]phenylalanine. The hyoscyamine and scopolamine isolated from the plants 7 days later were labeled with tritium, but devoid of ¹⁴C, indicating that 3-hydroxy-3-phenylpropanoic acid and cinnamic acid are not intermediates between phenylalanine and tropic acid. The [³H] tropic acid obtained by hydrolysis of the hyoscyamine was degraded and shown to have essentially all its tritium located at the para position of its phenyl group, a result consistent with previous work.     

New phosphonoformic acid derivatives of 3'-azido-3'-deoxythymidine

New 5'-alkyl ethoxy- and aminocarbonylphosphonates of 3'-azido-3'-deoxythymidine (AZT) were synthesized, and their antiviral properties in HIV-1-infected cell cultures and stability to chemical hydrolysis were studied. The AZT 5'-aminocarbonylphosphonates were shown to be significantly more stable in phosphate buffer (pH 7.2) than the corresponding ethoxycarbonylphosphonates. The therapeutic (selectivity) index of some of the compounds exceeded that of the parent AZT due to their higher antiviral activity. The English version of the paper: Russian Journal of Bioorganic Chemistry, 2004, vol. 30, no. 3; see also http://www.maik.ru.     

Catabolism of 2,4,5-trimethyoxybenzoic acid and 3-methoxycrotonic acid.

4-Methoxygentisic acid was an intermediate formed when Arthrobacter degraded, 2,4,5-trimethoxybenzoic acid. Isolates of Pseudomonas and Arthrobacter from soil grew at the expense of 3-methoxycrotonic acid. Evidence is presented that enzymatic hydration, with elimination of methanol, accounted for replacement of the methoxyl group of 3-methoxycrotonic acid and also of one methoxyl group of 2,4,5-trimethoxybenzoic acid.     

Synthesis of homohypotaurine (3-aminopropansulfinic acid) and homothiotaurine (3-aminopropanthiosulfonic acid)

A method is described for the chemical synthesis of homohypotaurine starting from homocystamine. By reaction of homohypotaurine with elemental sulfur, the corresponding thiosulfonic derivative, homothiotaurine, may be easily obtained. Homohypotaurine and homothiotaurine may be well separated from each other by paper or ion-exchange chromatography, and by paper electrophoresis, and are easily identified by some specific reactions.     

A role for 3-hydroxy-3-methyl-glutaric acid in the biosynthesis of pseudomonic acid A

Abstract [3-¹⁴C]3-Hydroxy-3-methyl-glutaric acid (HMG) was incorporated (0.9%) into pseudomonic acid A when administered to a shaken flask fermentation of Pseudomonas fluorescens 4, 9 and 14 h after inoculation. [2-¹⁴C]-Mevalonic acid was not incorporated into pseudomonic acid. Experimental evidence supports the previous deduction that pseudomonic acid biosynthesis might directly involve HMG, an apparently unusual intermediary metabolite in prokaryotes.     

Enzymatic esterification of 3-hydroxybutyric acid

Summary Candida cylindracea lipase catalysed esterification of (±)-3-hydroxybutyric acid (1) with n-butanol was studied in different solvents. This provided an alternative preparative method for the versatile chiron. butyl (S)-3-hydroxybutyrate (2) via kinetic resolution of (±)-1 With toluene as the reaction medium, the enantioselection was found to be excellent for 2 and moderate for the resolved acid (1).     

Synthesis of indole-3-acetylaspartic acid

A simple synthesis of indole-3-acetyl-d,l-aspartic acid and its l-isomer is described and their physical properties are listed.     

Production of a co-polyester of 3-hydroxybutyric acid and 3-hydroxyvaleric acid from succinic acid by Rhodococcus ruber: biosynthetic considerations

The biosynthesis of the 3-hydroxyvalerate (3HV) monomer of polyhydroxyalkanoate by Rhodococcus ruber from succinic acid was investigated using nuclear magnetic resonance analysis. Polymer produced from [2,3-¹³C]- and [1,4-¹³C]succinate showed that the C-1-C-2 and C-4-C-5 fragments of 3HV were derived from carbons 2 and 3 of succinate, essentially without bond cleavage, and carbon 3 of 3HV was derived from a carboxyl carbon of succinate. Using [1,2-¹³C]succinate it was demonstrated that the C-1-C-2 bond of succinate was cleaved during polymer biosynthesis. Methylmalonyl-coenzyme A (CoA) mutase activity was detected in cell-free extracts of R. ruber by enzyme assay and HPLC analysis of reaction products. A pathway, involving the known methylmalonyl-CoA pathway for propionate formation in Propionibacteria, followed by the established pathway for PHA biosynthesis from propionyl-CoA and acetyl-CoA, is proposed for the biosynthesis of 3HV from succinate by R. ruber. Correspondence to: A. J. Anderson     

Bile acid synthesis. Metabolism of 3 beta-hydroxy-5-cholenoic acid to chenodeoxycholic acid

Metabolism of 3 beta-hydroxy-5-cholenoic acid to chenodeoxycholic acid has been found to occur in rabbits and humans, species that cannot 7 alpha-hydroxylate lithocholic acid. This novel pathway for chenodeoxycholic acid synthesis from 3 beta-hydroxy-5-cholenoic acid led to a reinvestigation of the pathway for chenodeoxycholic acid from 3 beta-hydroxy-5-cholenoic acid in the hamster. Simultaneous infusion of equimolar [1,2-3H]lithocholic acid and 3 beta-hydroxy-5-[14C]cholenoic acid indicated that the 14C enrichment of chenodeoxycholic acid was much greater than that of lithocholic acid. Thus, in all these species, a novel 7 alpha-hydroxylation pathway exists that prevents the deleterious biologic effects of 3 beta-hydroxy-5-cholenoic acid.