Chiral-substrate-assisted stereoselective epoxidation catalyzed by H 2O 2-dependent cytochrome P450 SPα

Takashi Fujishiro, Osami Shoji, Norifumi Kawakami, Takahiro Watanabe, Hiroshi Sugimoto, Yoshitsugu Shiro, Yoshihito Watanabe

研究成果: Article査読

20 被引用数 (Scopus)

抄録

The stereoselective epoxidation of styrene was catalyzed by H 2O 2-dependent cytochrome P450 SPα in the presence of carboxylic acids as decoy molecules. The stereoselectivity of styrene oxide could be altered by the nature of the decoy molecules. In particular, the chirality at the α-positions of the decoy molecules induced a clear difference in the chirality of the product: (R)-ibuprofen enhanced the formation of (S)-styrene oxide, whereas (S)-ibuprofen preferentially afforded (R)-styrene oxide. The crystal structure of an (R)-ibuprofen-bound cytochrome P450 SPα (resolution 1.9 Å) revealed that the carboxylate group of (R)-ibuprofen served as an acid-base catalyst to initiate the epoxidation. A docking simulation of the binding of styrene in the active site of the (R)-ibuprofen-bound form suggested that the orientation of the vinyl group of styrene in the active site agreed with the formation of (S)-styrene oxide. The stereoselective epoxidation of styrene was catalyzed by H 2O 2-dependent cytochrome P450 SPα in the presence of carboxylic acids as decoy molecules. The stereoselectivity of the reaction could be altered by the nature of the decoy molecules, such as ibuprofen.

本文言語English
ページ(範囲)2286-2293
ページ数8
ジャーナルChemistry - An Asian Journal
7
10
DOI
出版ステータスPublished - 2012 10
外部発表はい

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

フィンガープリント 「Chiral-substrate-assisted stereoselective epoxidation catalyzed by H <sub>2</sub>O <sub>2</sub>-dependent cytochrome P450 <sub>SPα</sub>」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

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