Browse > Article
http://dx.doi.org/10.4014/jmb.1105.05049

Enzymatic Synthesis of L-tert-Leucine with Branched Chain Aminotransferase  

Seo, Young-Man (School of Biotechnology, Yeungnam University)
Yun, Hyung-Don (School of Biotechnology, Yeungnam University)
Publication Information
Journal of Microbiology and Biotechnology / v.21, no.10, 2011 , pp. 1049-1052 More about this Journal
Abstract
In this study, we demonstrated the asymmetric synthesis of L-tert-leucine from trimethylpyruvate using branched-chain aminotransferase (BCAT) from Escherichia coli in the presence of L-glutamate as an amino donor. Since BCAT was severely inhibited by 2-ketoglutarate, in order to overcome this here, we developed a BCAT/aspartate aminotransferase (AspAT) and BCAT/AspAT/pyruvate decarboxylase (PDC) coupling reaction. In the BCAT/AspAT/PDC coupling reaction, 89.2 mM L-tert-leucine (ee>99%) was asymmetrically synthesized from 100 mM trimethylpyruvate.
Keywords
Aminotransferase; branched-chain aminotransferase; coupling reaction; L-tert-leucine; unnatural amino acid;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By Web Of Science : 0  (Related Records In Web of Science)
연도 인용수 순위
1 Turner, N. J., J. R. Winterman, R. McCague, J. S. Parratt, and S. J. C. Taylor. 1995. Synthesis of homochiral $_L-$(S)-tert-leucine via a lipase catalysed dynamic resolution process. Tetrahedron Lett. 36: 1113-1136.   DOI   ScienceOn
2 Yun, H. and B. G. Kim. 2008. Enzymatic production of (R)- phenylacetylcarbinol by pyruvate decarboxylase from Zymomonas mobilis. Biotechnol. Bioprocess Eng. 13: 372-376.   DOI   ScienceOn
3 Zhu, D. and L. Hua. 2009. Biocatalytic asymmetric amination of carbonyl functional groups - a synthetic biology approach to organic chemistry. Biotechnol. J. 4: 1420-1431.   DOI   ScienceOn
4 Seo, Y. M., Y. H. Khang, and H. Yun. 2011. Kinetic resolution of 3-fluoroalanine using a fusion protein of $_D-amino$ acid oxidase with vitreoscilla hemoglobin. Biosci. Biotechnol. Biochem. 75: 820-822.   DOI   ScienceOn
5 Steward, J. D. 2001. Dehydrogenases and transaminases in asymmetric synthesis. Curr. Opin. Chem. Biol. 5: 120-129.   DOI   ScienceOn
6 Taylor, P. P., D. P. Pantaleone, R. F. Senkpeil, and I. G. Fotheringham. 1998. Novel biosynthetic approaches to the production of unnatural amino acids using transaminases. Trends Biotechnol. 16: 412-418.   DOI   ScienceOn
7 Hong, E. Y., M. Cha, H. Yun, and B. G. Kim. 2010. Asymmetric synthesis of $_L$-tert-leucine and $_L$-3-hydroxyadamantylglycine using branched chain aminotransferase. J. Mol. Catal. B Enzym. 66: 228-233.   DOI   ScienceOn
8 Li, T., A. B. Kootstra, and I. G. Fotheringham. 2002. Nonproteinogenic $\alpha$-amino acid preparation using equilibrium shifted transamination. Org. Proc. Res. Dev. 6: 533-538.   DOI   ScienceOn
9 Liu, S. L., Q. X. Song, D. Z. Wei, Y. W. Zhang, and X. D. Wang. 2006. Preparation of optically pure tert-leucine by penicillin G acylase-catalyzed resolution. Prep. Biochem. Biotech. 36: 235-241.   DOI   ScienceOn
10 Liu, S. L., D. Z. Wei, Q. X. Song, Y. W. Zhang, and X. D. Wang. 2006. Effect of organic cosolvent on kinetic resolution of tert-leucine by penicillin G acylase from Kluyvera citrophila. Bioproc. Biosyst. Eng. 28: 285-289.   DOI   ScienceOn
11 Ma, J. A. 2003. Recent developments in the catalytic asymmetric synthesis of $\alpha-$ and $\beta-$amino acids. Angew. Chem. Int. Edit. 42: 4290-4299.   DOI   ScienceOn
12 Schmidt, E., B. Bossow, R. Wichmann, and C. Wandrey. 1986. Enzyme membrane reactor - an alternative approach for continuous operation with enzymes. Kem. Ind. 35: 71-77.
13 Hwang, B. Y., B. K. Cho, H. Yun, K. Koteshwar, and B. G. Kim. 2005. Revisit of aminotransferase in the genomic era and its application to biocatalysis. J. Mol. Catal. B Enzym. 37: 47-55.   DOI   ScienceOn
14 Allenmark, S. and B. Lamm. 2001. A useful route to (R)- and (S)-tert-leucine. Chirality 13: 43-47.   DOI   ScienceOn
15 Bea, H. S., H. J. Park, S. H. Lee, and H. Yun. 2011. Kinetic resolution of aromatic $\beta$-amino acids by $\omega$-transaminase. Chem. Commun. 47: 5894-5896.   DOI   ScienceOn
16 Bommarius, A. S., M. Schwarm, and K. Drauz. 1998. Biocatalysis to amino acid-based chiral pharmaceuticals - examples and perspectives. J. Mol. Catal. B Enzym. 5: 1-11.   DOI