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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 | |
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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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× Kyle, Stanfield Joshua× Shoji, Osami× Yanagisawa, Sota× Sugimoto, Hiroshi× Shiro, Yoshitsugu× 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 |
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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 |