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  1. B100 理学部/理学研究科
  2. B100a 雑誌掲載論文
  3. 学術雑誌

Control of stereoselectivity of benzylic hydroxylation catalysed by wild-type cytochrome P450BM3 using decoy molecules

http://hdl.handle.net/2237/27359
25e3fb1d-84da-4146-a1d6-6bf4c2aa3ff0
名前 / ファイル ライセンス アクション
RSC_draft_final_Josh.pdf RSC_draft_final_Josh.pdf ファイル公開日:2018/08/07 (1.4 MB)
Item type 学術雑誌論文 / Journal Article(1)
公開日 2018-02-05
タイトル
タイトル Control of stereoselectivity of benzylic hydroxylation catalysed by wild-type cytochrome P450BM3 using decoy molecules
著者 Suzuki, Kazuto

× Suzuki, Kazuto

WEKO 75025

Suzuki, Kazuto

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Kyle, Stanfield Joshua

× Kyle, Stanfield Joshua

WEKO 75026

Kyle, Stanfield Joshua

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Shoji, Osami

× Shoji, Osami

WEKO 75027

Shoji, Osami

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Yanagisawa, Sota

× Yanagisawa, Sota

WEKO 75028

Yanagisawa, Sota

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Sugimoto, Hiroshi

× Sugimoto, Hiroshi

WEKO 75029

Sugimoto, Hiroshi

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Shiro, Yoshitsugu

× Shiro, Yoshitsugu

WEKO 75030

Shiro, Yoshitsugu

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Watanabe, Yoshihito

× Watanabe, Yoshihito

WEKO 75031

Watanabe, Yoshihito

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抄録
内容記述 The hydroxylation of non-native substrates catalysed by wild-type P450BM3 is reported, wherein “decoy molecules”, i.e., native substrate mimics, controlled the stereoselectivity of hydroxylation reactions. We employed decoy molecules with diverse structures, resulting in either a significant improvement in enantioselectivity or clear inversion of stereoselectivity in the benzylic hydroxylation of alkylbenzenes and cycloalkylbenzenes. For example, supplementation of wild-type P450BM3 with 5-cyclohexylvaleric acid-L-phenylalanine (5CHVA-Phe) and Z-proline-L-phenylalanine yielded 53% (R) ee and 56% (S) ee for indane hydroxylation, respectively, although 16% (S) ee was still observed in the absence of any additives. Moreover, we performed a successful crystal structure analysis of 5CHVA-L-tryptophan-bound P450BM3 at 2.00 Å, which suggests that the changes in selectivity observed were caused by conformational changes in the enzyme induced by binding of the decoy molecules.
内容記述タイプ Abstract
出版者
出版者 Royal Society of Chemistry
言語
言語 eng
資源タイプ
資源タイプresource http://purl.org/coar/resource_type/c_6501
タイプ journal article
ISSN
収録物識別子タイプ ISSN
収録物識別子 2044-4753
書誌情報 Catalysis Science and Technology

巻 7, p. 3332-3338, 発行日 2017-08-07
著者版フラグ
値 author
URI
識別子 http://doi.org/10.1039/C7CY01130J
識別子タイプ DOI
URI
識別子 http://hdl.handle.net/2237/27359
識別子タイプ HDL
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