Enzymatic synthesis of L-6-hydroxynorleucine

被引：61

作者：

Hanson, RL

Schwinden, MD

Banerjee, A

Brzozowski, DB

Chen, BC

Patel, BP

McNamee, CG

Kodersha, GA

Kronenthal, DR

Patel, RN

Szarka, LJ

机构：

[1] Bristol Myers Squibb, Dept Microbial Technol, New Brunswick, NJ 08903 USA

[2] Bristol Myers Squibb, Chem Proc Res, Princeton, NJ 08540 USA

[3] Bristol Myers Squibb, Chem Proc Dev, New Brunswick, NJ 08903 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 1999年 / 7卷 / 10期

关键词：

L-6-hydroxynorleucine; glutamate dehydrogenase; phenylalanine dehydrogenase; D-amino acid oxidase; 2-keto-6-hydroxyhexanoic acid;

D O I：

10.1016/S0968-0896(99)00158-3

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

引用

页码：2247 / 2252

页数：6

共 18 条

[1] A NOVEL SYNTHETIC ROUTE TO ENANTIOMERS OF EPSILON-HYDROXYNORLEUCINE AND EPSILON-CHLORONORLEUCINE FROM L-LYSINE AND D,L-LYSINE [J].