The Stereochemical Course of the Water Elimination from (2R)-Phenyllactate in the Amino Acid Fermentation ofClostridium sporogenes

Publisher Website
Google Scholar
Abstract
(2R,3R)-[3-3H]- and (2R,3S)-[3-3H]-phenyllactate were synthesized from phenylpyruvate with the help of phenylpyruvate tautomerase (EC 5.3.2.1.) and an NADH-dependent 2-oxo-acid reductase from C. sporogenes. With whole cells of C. sporogenes both (2R)-phenyllactates are mainly transformed to phenylpropionate and to a minor extent to phenylalanine. According to recently published results, transformation of phenyllactate to phenylpropionate, or an activated derivative of it, leads to (E)-cinnamate which is reduced to phenylpropionate in a fast consecutive reaction. The 3H/14C-ratio of phenylpropionate deriving from (2R,3R)-[3-3H,U-14C]phenyllactate was about 85% of that of the phenyllactate and the corresponding ratio for phenylpropionate deriving from the (2R,3S)-[3-3H,U-14C]phenyllactate about 7%, respectively. Assuming that the E-configuration of cinnamate is formed directly from (2R)-phenyllactate, the water elimination occurs in a syn fashion.

This publication has 6 references indexed in Scilit: