Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 357, Issue 4, Pages 767-774Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201400672
Keywords
enzymatic synthesis; beta-hydroxy alpha-amino acids; iron(II)/alpha-ketoglutarate-dependent dioxygenase; N-succinyl L-amino acid desuccinylase
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Funding
- Ministry of Education, Culture, Sports, Science and Technology of Japan [21780070]
- Project for Development of a Technological Infrastructure for Industrial Bioprocesses on R&D of New Industrial Science and Technology Frontiers from the New Energy and Industrial Technology Development Organization (NEDO) of Japan
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A novel enzymatic production system of optically pure beta-hydroxy alpha-amino acids was developed. Two enzymes were used for the system: an N-succinyl l-amino acid beta-hydroxylase (SadA) belonging to the iron(II)/alpha-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 beta-hydroxy l-amino acids, such as N-succinyl-l-beta-hydroxyvaline, N-succinyl-l-threonine, (2S, 3R)-N-succinyl-l beta-hydroxyisoleucine, and N-succinyl-l-threo-beta-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-beta-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 beta-hydroxy alpha-amino acids.
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