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

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.