Stereochemistry of the conversion of methacrylate to β-hydroxyisobutyrate in Pseudomonas putida
- 1 January 1979
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- Vol. 4 (4), 939-942
- https://doi.org/10.1039/p19790000939
Abstract
Stereospecifically labelled (2S,3S+ 2R,3R)-[2,3-2H2]-β-hydroxyisobutyric acid methyl ester benzoate was synthesized and used to assign the Eu(fod)3 shifted n.m.r. signals of the C-3 hydrogens of the unlabelled analogue. (E)-[3-2H1]Methacrylic acid was converted by Pseudomonas putida(ATCC 21244) to (2S,3S)-[3-2H1]-β-hydroxyisobutyric acid. The results show that the hydration of methacrylate to S-(+)-β-hydroxyisobutyric acid in this organism, probably via methacrylyl-CoA, proceeds stereospecifically by syn hydration.This publication has 3 references indexed in Scilit:
- A stereochemical study on the metabolism of isobutyrate in Pseudomonas putidaBioorganic Chemistry, 1977
- The Absolute Configuration of Methylmalonyl Coenzyme A and Stereochemistry of the Methylmalonyl Coenzyme A Mutase ReactionJournal of Biological Chemistry, 1966
- ZUR BIOCHEMISCHEN FUNKTION DES BIOTINS .9. DER STERISCHE VERLAUF DER CARBOXYLIERUNG VON PROPIONYL-COA1965