Multi-Enzymatic Synthesis of Optically Pure β-Hydroxy α-Amino Acids

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바이오화학분류

- 바이오플라스틱
  1. 고무
  2. 플라스틱
- 바이오정밀화학
  1. 용매
  2. 화학제품
- 화장품용 기능성소재
  1. 계면활성제⁄증점제
- 의료용 화학소재
  1. 식품첨가제

논문

Multi-Enzymatic Synthesis of Optically Pure β-Hydroxy α-Amino Acids

학술지

Advanced synthesis & catalysis

저자명

Hibi, Makoto; Kasahara, Takuya; Kawashima, Takashi; Yajima, Hiroko; Kozono, Shoko; Smirnov, Sergey V.; Kodera, Tomohiro; Sugiyama, Masakazu; Shimizu, Sakayu; Yokozeki, Kenzo; Ogawa, Jun

초록

AbstractA novel enzymatic production system of optically pure β‐hydroxy α‐amino acids was developed. Two enzymes were used for the system: an N‐succinyl L‐amino acid β‐hydroxylase (SadA) belonging to the iron(II)/α‐ketoglutarate‐dependent dioxygenase superfamily and an N‐succinyl L‐amino acid desuccinylase (LasA). The genes encoding the two enzymes are part of a gene set responsible for the biosynthesis of peptidyl compounds found in the Burkholderia ambifaria AMMD genome. SadA stereoselectively hydroxylated several N‐succinyl aliphatic L‐amino acids and produced N‐succinyl β‐hydroxy L‐amino acids, such as N‐succinyl‐L‐β‐hydroxyvaline, N‐succinyl‐L‐threonine, (2S,3R)‐N‐succinyl‐L‐β‐hydroxyisoleucine, and N‐succinyl‐L‐threo‐β‐hydroxyleucine. LasA catalyzed the desuccinylation of various N‐succinyl‐L‐amino acids. Surprisingly, LasA is the first amide bond‐forming enzyme belonging to the amidohydrolase superfamily, and has succinylation activity towards the amino group of L‐leucine. By combining SadA and LasA in a preparative scale production using N‐succinyl‐L‐leucine as substrate, 2.3 mmol of L‐threo‐β‐hydroxyleucine were successfully produced with 93% conversion and over 99% of diastereomeric excess. Consequently, the new production system described in this study has advantages in optical purity and reaction efficiency for application in the mass production of several β‐hydroxy α‐amino acids.

발행연도

2015

ISSN

1615-4150

ISSN

1615-4169

권

357

호

페이지

pp.767-774

DOI