Residue size at position 87 of cytochrome P450 BM‐3 determines its stereoselectivity in propylbenzene and 3‐chlorostyrene oxidation

FEBS Letters

Ogawa, Jun¹  Shimizu, Sakayu¹  Li, Qing-Shan¹  Schmid, Rolf D² 

[1] Division of Applied Life Science, Graduate School of Agriculture, Kyoto University, Kitashirakawa-oiwakecho, Sakyo-ku, Kyoto 606-8502, Japan;Institut für Technische Biochemie, Universität Stuttgart, Allmandring 31, D-70459 Stuttgart, Germany

关键词: Cytochrome P450;    Cytochrome P450 BM-3;    Oxidation;    Stereoselectivity;    Propylbenzene;    3-Chlorostyrene;    P450;    cytochrome P450;    WT;    wild-type P450 BM-3;    F87V;    F87A;    and F87G;    P450 BM-3 mutants;   

DOI  :  10.1016/S0014-5793(01)03074-5

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

We report here oxidation of propylbenzene and 3-chlorostyrene by wild-type cytochrome P450 BM-3 with high turnover (479 nmol 1-phenyl-1-propanol/min/nmol P450 and 300 nmol 3-chlorostyrene oxide/min/nmol P450). Furthermore, the residue size at position 87 of P450 BM-3 was found to play critical roles in determining stereoselectivity in oxidation of propylbenzene and 3-chlorostyrene. Replacement of Phe87 with Val, Ala and Gly resulted in decreases in optical purity of produced (R)-(+)-1-phenyl-1-propanol from 90.0 to 37.4, 26.0 and −15.6% e.e., respectively, and in increases in those of produced (R)-(+)-3-chlorostyrene oxide from −61.0 to −38.0, 67.0 and 94.6% e.e., respectively.

【 授权许可】

Unknown