Wang Mei-Xiang, Wu Yan
Laboratory of Chemical Biology, Centre for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China.
Org Biomol Chem. 2003 Feb 7;1(3):535-40. doi: 10.1039/b209791e.
Catalysed by the nitrile hydratase/amidase-containing Rhodococcus sp. AJ270 cells, a number of beta-aryl- and beta-alkyl- beta-hydroxy-alpha-methylenepropiononitriles (the Baylis-Hillman nitriles) 1 underwent hydrolysis under mild conditions to produce the corresponding enantiomerically enriched Baylis-Hillman amides 2 and acids 3. The enantioselectivity of the biotransformations was strongly determined by the steric effect of the substituents at the beta-position of the substrates. The protection of the free hydroxy of beta-phenyl-beta-hydroxy-alpha-methylenepropiononitrile 1a by methylation led to the enhancement of enantiocontrol of the biohydrolysis.
在含有腈水合酶/酰胺酶的红球菌属AJ270细胞的催化下，多种β-芳基和β-烷基-β-羟基-α-亚甲基丙腈（贝利斯-希尔曼腈）1在温和条件下发生水解，生成相应的对映体富集的贝利斯-希尔曼酰胺2和酸3。生物转化的对映选择性很大程度上由底物β位取代基的空间效应决定。β-苯基-β-羟基-α-亚甲基丙腈1a的游离羟基通过甲基化进行保护，导致生物水解的对映体控制增强。
