Kinetic resolution of amines by (R)-selective omega-transaminase from Mycobacterium vanbaalenii

Giyoung Shin; Sam Mathew; Hyungdon Yun

Journal of Industrial and Engineering Chemistry, Vol.23, 128-133, March, 2015

DOI10.1016/j.jiec.2014.08.003 Export Citation

Kinetic resolution of amines by (R)-selective omega-transaminase from Mycobacterium vanbaalenii

Giyoung Shin, Sam Mathew, and Hyungdon Yun^{1, †}

School of Biotechnology, Yeungnam University, Gyeongsan, Gyeongbuk 712-749, Republic of Korea
¹Department of Bioscience & Biotechnology, Konkuk University, Seoul 143-701, Republic of Korea

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Recently (R)-selective ω-transaminase ((R)-ω-TAMV) from Mycobacterium vanbaalenii was discovered and utilized for the asymmetric synthesis of (R)-amines from its corresponding ketones. In this study, (R)-ω-TAMV was used for the kinetic resolution of racemic amines to produce (S)-amines. (R)-ω-TAMV showed very low product inhibition by ketone product (acetophenone), which is beneficial for carrying out the kinetic resolution of racemic amines with high concentration. 100 mM racemic amines were successfully resolved into (S)-amines (>99% ee) by (R)-ω-TAMV with pyruvate. In addition, the kinetic resolution of α-MBA was successfully carried out by using acetone as an amino acceptor which is cheaper than pyruvate.

Keywords:Chiral amine;Enantioselectivity;Enzyme catalysis;Kinetic resolution;ω-Transaminase

[References]

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Truppo MD, Turner NJ, Rozzell JD, Chem. Commun., 28, 2127 (2009)
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[1] Schatzle S, Steffen-Munsberg F, Thontowi A, Hohne M, Robins K, Bornscheuer UT, Adv. Synth. Catal., 353, 2439 (2011)

[2] Paetzold J, Backvall JE, J. Am. Chem. Soc., 127(50), 17620 (2005)

[3] Hohne M, Bornscheuer UT, ChemCatChem, 1, 42 (2009)

[4] Mathew S, Yun H, ACS Catal., 2, 993 (2012)

[5] Deepankumar K, Shon M, Nadarajan SP, Shin G, Mathew S, Ayyadurai N, Kim BG, Choi SH, Lee SH, Yun H, Adv. Synth. Catal., 356, 993 (2014)

[6] Paul CE, Rodrıguez-Mata M, Busto E, Lavandera I, Gotor-Fernandez V, Gotor V, Garcıa-Cerrada S, Mendiola J, Frutos O, Collado I, Org. Process Res. Dev., 18, 788 (2014)

[7] Simon RC, Richter N, Busto E, Kroutil W, ACS Catal., 4, 129 (2014)

[8] Kroutil W, Fischereder EM, Fuchs CS, Lechner H, Mutti FG, Pressnitz D, Rajagopalan A, Sattler JH, Simon RC, Siirola E, Org. Process Res. Dev., 17, 751 (2013)

[9] Bea HS, Park HJ, Lee SH, Yun H, Chem. Commun., 47, 5894 (2011)

[10] Mutti FG, Fuchs CS, Pressnitz D, Sattler JH, Kroutil W, Adv. Synth. Catal., 353, 3227 (2011)

[11] Mathew S, Shin G, Shon M, Yun H, Biotechnol. Bioprecess E, 18, 1 (2013)

[12] Malik MS, Park ES, Shin JS, Green Chem., 14, 2137 (2012)

[13] Desai AA, Angew. Chem.-Int. Edit., 50, 1974 (2011)

[14] Koszelewski D, Tauber K, Faber K, Kroutil W, Trends Biotechnol., 28, 324 (2010)

[15] Malik MS, Park ES, Shin JS, Appl. Microbiol. Biotechnol., 94(5), 1163 (2012)

[16] Shin G, Mathew S, Shon M, Kim BG, Yun H, Chem. Commun., 49, 8629 (2013)

[17] Yun H, Kim BG, Biosci. Biotechnol. Biochem., 72, 3030 (2008)

[18] Shin JS, Kim BG, Biotechnol. Bioeng., 65(2), 206 (1999)

[19] Truppo MD, Turner NJ, Rozzell JD, Chem. Commun., 28, 2127 (2009)

[20] Iwasaki A, Yamada Y, Kizaki N, Ikenaka Y, Hasegawa J, Appl. Microbiol. Biotechnol., 69(5), 499 (2006)

[21] Iwasaki A, Matsumoto K, Hasegawa J, Yasohara Y, Appl. Microbiol. Biotechnol., 93(4), 1563 (2012)

[22] Hohne M, Schatzle S, Jochens H, Robins K, Bornscheuer UT, Nat. Chem. Biol., 6, 807 (2010)

[23] Bea HS, Seo YM, Cha MH, Kim BG, Yun H, Biotechnol. Bioprocess E, 15, 429 (2010)

[24] Shin JS, Kim BG, Biosci. Biotechnol. Biochem., 65, 1782 (2001)

[25] Park ES, Shin JS, Appl. Environ. Microbiol., 79, 4141 (2013)