Isolation, identification and characterization of marine bacteria exhibiting complementary enantioselective epoxide hydrolase activity for preparing chiral chlorinated styrene oxide derivatives

Jung-Hee Woo; Kyoung-Myoung Kang; Tae-Hyung Kwon; Nyun-Ho Park; Eun Yeol Lee

Journal of Industrial and Engineering Chemistry, Vol.28, 225-228, August, 2015

DOI10.1016/j.jiec.2015.02.018 Export Citation

Isolation, identification and characterization of marine bacteria exhibiting complementary enantioselective epoxide hydrolase activity for preparing chiral chlorinated styrene oxide derivatives

Jung-Hee Woo^†, Kyoung-Myoung Kang, Tae-Hyung Kwon, Nyun-Ho Park, and Eun Yeol Lee^{1, †}

Gyeongbuk Institute for Marine Bio-Industry (GIMB), Uljin 767-813, Gyeongbuk, Republic of Korea
¹Department of Chemical Engineering, Kyung Hee University, Gyeonggi-do 446-701, Republic of Korea

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Marine bacteria possessing epoxide hydrolase (EH) activity were isolated from the oil-spilled foreshore of South Korea. While the isolated Rhodococcus sp. YSMI04 and YSNA32 showed different enantioselectivities to racemic styrene oxide (SO), two strains exhibited same enantiopreference to 3-chlorostyrene oxide (3-CSO) and 4-CSO. In the case of 3-CSO, Rhodococcus sp. YSMI04 and YSNA32 exhibited (R)-3-CSO preferred hydrolysis activity, whereas Roseobacter sp. TSBP12 showed a preference for (S)-3-CSO. In the case of 4-CSO, Rhodococcus sp. YSMI04 and YSNA32 showed enantiopreference to (S)-4-CSO, Roseobacter sp. TSBP12 exhibited (R)-4-CSO preferred activity. (S)-4-CSO was obtained with 35% yield (theoretically 50%) using Roseobacter sp. TSBP12.

Keywords:Epoxide hydrolase;Rhodococcus sp. YSMI04;Rhodococcus sp. YSNA32;Roseobacter sp. TSBP12;Styrene oxide

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Yoon TP, Jacobsen EN, Science, 299, 1691 (2003)
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Yildirim D, Tukel SS, Alagoz D, Alptekin O, Enzyme Microb. Technol., 49(6-7), 555 (2011)
Kim YH, Lee I, Choi SH, Lee OK, Sim J, Lee J, Kim J, Lee EY, J. Mol. Catal. B-Enzym., 89, 48 (2013)
Reetz MT, Adv. Catal., 49, 1 (2006)
van Loo B, Spelberg JHL, Kingma J, Sonke T, Wubbolts MG, Janssen DB, Chem. Biol., 11, 981 (2004)
Kotik M, Stepanek V, Kyslık P, Maresova H, J. Biotechnol., 132, 8 (2007)
Weijers CAGM, de Bont JAM, J. Mol. Catal. B-Enzym., 6, 199 (1999)
Xu X, Xu JH, Pan J, Gu O, Wu XY, Org. Lett., 8, 1737 (2006)
Woo JH, Kang JH, Kang S, Hwang YO, Kim SJ, Appl. Microbiol. Biotechnol., 82(5), 873 (2009)
Woo JH, Kang JH, Hwang YO, Cho JC, Kim SJ, Kang SG, J. Biosci. Bioeng., 109(6), 539 (2010)
Woo JH, Kwon TH, Kim JT, Kim CG, Lee EY, Biotechnol. Lett., 35(4), 599 (2013)

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[1] Breuer M, Ditrich K, Habicher T, Hauer B, Kesseler M, Sturmer R, Zelinski T, Angew. Chem.-Int. Edit., 43, 788 (2004)

[2] Yoon TP, Jacobsen EN, Science, 299, 1691 (2003)

[3] de Vries EJ, Janssen DB, Curr. Opin. Biotechnol., 14, 414 (2003)

[4] Lee EY, Shuler ML, Biotechnol. Bioeng., 98(2), 318 (2007)

[5] Lee KS, Woo MH, Kim HS, Lee EY, Lee IS, Chem. Commun., 25, 3780 (2009)

[6] Yildirim D, Tukel SS, Alagoz D, Alptekin O, Enzyme Microb. Technol., 49(6-7), 555 (2011)

[7] Kim YH, Lee I, Choi SH, Lee OK, Sim J, Lee J, Kim J, Lee EY, J. Mol. Catal. B-Enzym., 89, 48 (2013)

[8] Reetz MT, Adv. Catal., 49, 1 (2006)

[9] van Loo B, Spelberg JHL, Kingma J, Sonke T, Wubbolts MG, Janssen DB, Chem. Biol., 11, 981 (2004)

[10] Kotik M, Stepanek V, Kyslık P, Maresova H, J. Biotechnol., 132, 8 (2007)

[11] Weijers CAGM, de Bont JAM, J. Mol. Catal. B-Enzym., 6, 199 (1999)

[12] Xu X, Xu JH, Pan J, Gu O, Wu XY, Org. Lett., 8, 1737 (2006)

[13] Woo JH, Kang JH, Kang S, Hwang YO, Kim SJ, Appl. Microbiol. Biotechnol., 82(5), 873 (2009)

[14] Woo JH, Kang JH, Hwang YO, Cho JC, Kim SJ, Kang SG, J. Biosci. Bioeng., 109(6), 539 (2010)

[15] Woo JH, Kwon TH, Kim JT, Kim CG, Lee EY, Biotechnol. Lett., 35(4), 599 (2013)