Enzymatic synthesis of L-6-hydroxynorleucine
Enzymatic synthesis of L-6-hydroxynorleucine
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DOI：
10.1016/s0968-0896(99)00158-3
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发表时间：
1999-10-01
影响因子：
3.5
通讯作者：
Szarka, LJ
中科院分区：
文献类型：
--
作者：
Hanson, RL;Schwinden, MD;Szarka, LJ
l -6-羟基去甲亮氨酸是合成血管肽酶抑制剂的关键手性中间体，利用牛肝中的谷氨酸脱氢酶将2-酮-6-羟基己酸还原胺化，收率为89%，光学纯度为bb0 - 99%。用d -氨基酸氧化酶对5-（4-羟基丁基）海因水解制得的外消旋6-羟基去甲亮氨酸进行处理，制得2-酮-6-羟基己酸和l -6-羟基去甲亮氨酸的混合物，再进行还原胺化反应，将混合物全部转化为l -6-羟基去甲亮氨酸，收率为91 ~ 97%，光学纯度为bb0 ~ 99%。1999爱思唯尔科学有限公司版权所有。
L-6-Hydroxynorleucine, a key chiral intermediate used for synthesis of a vasopeptidase inhibitor, was prepared in 89% yield and > 99% optical purity by reductive amination of 2-keto-6-hydroxyhexanoic acid using glutamate dehydrogenase from beef liver, In an alternate process, racemic 6-hydroxynorleucine produced by hydrolysis of 5-(4-hydroxybutyl)hydantoin was treated with D-annino acid oxidase to prepare a mixture containing 2-keto-6-hydroxyhexanoic acid and L-6-hydroxynorleucine followed by the reductive amination procedure to convert the mixture entirely to L-6-hydroxynorleucine, with yields of 91 to 97% and optical purities of >99%. (C) 1999 Elsevier Science Ltd. All rights reserved.