Transaminase-catalyzed asymmetric synthesis of L-2-aminobutyric acid from achiral reactants

Biotechnology Letters

Volumn 31, Issue 10, 2009, Pages 1595-1599

  Shin, Jong Shik ^a   Kim, Byung Gee ^b  

^a Yonsei University   (South Korea)

^b Seoul National University   (South Korea)

Author keywords

2 Aminobutyric acid; Asymmetric synthesis; Biphasic reaction; Product inhibition; Transaminase

Indexed keywords

2-AMINOBUTYRIC ACID; ASYMMETRIC SYNTHESIS; BIPHASIC REACTION; PRODUCT INHIBITION; TRANSAMINASE;

ALDEHYDES; AMINES; ELECTRON TRANSITIONS; HEXANE; ORGANIC ACIDS; SYNTHESIS (CHEMICAL);

AMINO ACIDS;

2 OXOBUTYRIC ACID; ALPHA-KETOBUTYRIC ACID; AMINOBUTYRIC ACID DERIVATIVE; AMINOTRANSFERASE; BENZALDEHYDE; BENZALDEHYDE DERIVATIVE; BENZYLAMINE; BENZYLAMINE DERIVATIVE; BUTYRIC ACID DERIVATIVE; BUTYRINE; ENZYME INHIBITOR;

ARTICLE; ENZYMOLOGY; METABOLISM; STEREOISOMERISM; VIBRIO;

AMINOBUTYRIC ACIDS; BENZALDEHYDES; BENZYLAMINES; BUTYRIC ACIDS; ENZYME INHIBITORS; STEREOISOMERISM; TRANSAMINASES; VIBRIO;

VIBRIO FLUVIALIS;

EID: 70350116632     PISSN: 01415492     EISSN: 15736776     Source Type: Journal    
DOI: 10.1007/s10529-009-0057-7     Document Type: Article

References (14)

1. Ager DJ, Fotheringham IG (2001) Methods for the synthesis of unnatural amino acids. Curr Opin Drug Discov Dev 4:800-807.
2. Cho BK, Cho HJ, Park SH, Yun H, Kim BG (2003) Simultaneous synthesis of enantiomerically pure (S)-amino acids and (R)-amines using coupled transaminase reactions. Biotechnol Bioeng 81:783-789.
3. Gonalves LPB, Antunes OAC, Pinto GF, Oestreicher EG (2000) Simultaneous enzymatic synthesis of (S)-3-fluoroalanine and (R)-3-fluorolactic acid. Tetrahedron Asymmetry 11:1465-1468.
4. Hanzawa S, Oe S, Tokuhisa K, Kawano K, Kobayashi T, Kudo T, Kakidani H (2001) Chemo-enzymatic synthesis of 3-(2-naphthyl)-l-alanine by an aminotransferase from the extreme thermophile, Thermococcus profundus. Biotechnol Lett 23:589-591.
5. Li T, Kootstra AB, Fotheringham IG (2002) Nonproteinogenic α-amino acid preparation using equilibrium shifted transamination. Org Proc Res Dev 6:533-538.
6. Rouhi AM (2004) Chiral chemistry. Chem Eng News 82:47-62.
7. Schmid A, Dordick JS, Hauer B, Kiener A, Wubbolts M, Witholt B (2001) Industrial biocatalysis today and tomorrow. Nature 409:258-268.
8. Schoemaker HE, Mink D, WubboLts MG (2003) Dispelling the myths-biocatalysis in industrial synthesis. Science 299:1694-1697.
9. Shin JS, Kim BG (2002a) Exploring the active site of amine:pyruvate aminotransferase on the basis of the substrate structure-reactivity relationship: How the enzyme controls substrate specificity and stereoselectivity. J Org Chem 67:2848-2853.
10. Shin JS, Kim BG (2002b) Substrate inhibition mode of ω-transaminase from Vibrio fluvialis JS17 is dependent on the chirality of substrate. Biotechnol Bioeng 77:832-837.
11. Shin JS, Kim BG, Liese A, Wandrey C (2001) Kinetic resolution of chiral amines with ω-transaminase using an enzyme-membrane reactor. Biotechnol Bioeng 73:179-187.
12. Shin JS, Yun H, Jang JW, Park I, Kim BG (2003) Purification, characterization, and molecular cloning of a novel amine: pyruvate transaminase from Vibrio fluvialis JS17. Appl Microbiol Biotechnol 61:463-471.
13. Stewart JD (2001) Dehydrogenases and transaminases in asymmetric synthesis. Curr Opin Chem Biol 5:120-129.
14. Taylor PP, Pantaleone DP, Senkpeil RF, Fotheringham IG (1998) Novel biosynthetic approaches to the production of unnatural amino acids using transaminases. Trends Biotechnol 16:412-418.