Ene-Reductase Catalyzed Regio- and Stereoselective 1,4-Mono-Reduction of Pseudoionone to Geranylacetone,ChemCatChem

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Ene-Reductase Catalyzed Regio- and Stereoselective 1,4-Mono-Reduction of Pseudoionone to Geranylacetone
ChemCatChem ( IF 3.8 ) Pub Date : 2021-12-02 , DOI: 10.1002/cctc.202101557
Isabel Oroz-Guinea ₁ , Christoph Winkler ₂ , Silvia Glueck ₁ , Klaus Ditrich ₃ , Melanie Weingarten ₃ , Michael Breuer ₃ , Doreen Schachtschabel ₃ , Wolfgang Kroutil ₄

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Enzyme-catalyzed reduction: This work describes the exquisite regio- and stereoselectivity of OYE1 for the reduction of pseudoionone and 6-methyl-3,5-heptadien-2-one to geranylacetone and 6-methyl-5-hepten-2-one, respectively. This resulted in excellent conversions (>99 % and 97 %) and isolation yields (80 % and 77 %). Additionally, selective reduction of (E,E)- over the (E,Z)-pseudoionone was investigated using the ene-reductase from Zymomonas mobilis (NCR), obtaining both (E)-geranylacetone and (E,Z)-pseudoionone with isomeric excess above 60 %.

中文翻译：

烯还原酶催化假紫罗兰酮的区域选择性和立体选择性 1,4-单还原为香叶基丙酮

酶催化还原：这项工作描述了 OYE1 出色的区域选择性和立体选择性，用于将假紫罗兰酮和 6-甲基-3,5-庚二烯-2-酮还原为香叶丙酮和 6-甲基-5-庚烯-2-酮，分别。这导致了出色的转化率（>99% 和 97%）和分离产率（80% 和 77%）。此外，使用来自运动发酵单胞菌(NCR)的烯还原酶研究了 ( E , E )-相对于 ( E , Z )-假紫罗兰酮的选择性还原，获得 ( E )-香叶基丙酮和 ( E , Z )-假紫罗兰酮异构体过量超过 60%。

更新日期：2022-01-23

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