Pitsch C, Simon H
Hoppe Seylers Z Physiol Chem. 1982 Oct;363(10):1253-7. doi: 10.1515/bchm2.1982.363.2.1253.
(2R,3R)-[3-3H]- and (2R,3S)-[3-3H]- phenyllactate were synthesized from phenylpyruvate with the help of phenylpyruvate tautomerase and an NADH-dependent 2-oxo-acid reductase from Clostridium 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, the former transformation leads from phenyllactate, or an activated derivative of it, 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.
在产孢梭菌的苯丙酮酸互变异构酶和一种依赖NADH的2-氧代酸还原酶的帮助下，由苯丙酮酸合成了(2R,3R)-[3-³H]-和(2R,3S)-[3-³H]-苯乳酸。对于产孢梭菌的全细胞，两种(2R)-苯乳酸主要转化为苯丙酸，少量转化为苯丙氨酸。根据最近发表的结果，前一种转化从苯乳酸或其活化衍生物生成(E)-肉桂酸，后者在快速连续反应中还原为苯丙酸。由(2R,3R)-[3-³H,U-¹⁴C]苯乳酸生成的苯丙酸的³H/¹⁴C比值约为苯乳酸的85%，而由(2R,3S)-[3-³H,U-¹⁴C]苯乳酸生成的苯丙酸的相应比值约为7%。假设肉桂酸的E-构型直接由(2R)-苯乳酸形成，则水的消除以顺式方式发生。
