Novel reductase participation in the syn-addition of hydrogen to the C=C bond of enones in the cultured cells of Nicotiana tabacum

被引：27

作者：

Shimoda, K ^{[1
]}

Ito, DI ^{[1
]}

Izumi, S ^{[1
]}

Hirata, T ^{[1
]}

机构：

[1] HIROSHIMA UNIV,FAC SCI,DEPT CHEM,HIGASHIHIROSHIMA 739,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 04期

关键词：

D O I：

10.1039/p19960000355

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A reductase isolated from cultured cells of Nicotiana tabacum has been characterized and used in the reduction of a C=C bond adjacent to a carbonyl group, The stereochemistry of the latter reaction has been investigated by H-2 NMR and mass spectroscopy. It was found that the reductase reduces stereospecifically the C=C bond of verbenone and carvone by syn addition of hydrogen from the re face at the beta-position and the re face at the alpha-position to the carbonyl group; the hydrogen atoms participating in the enzymatic reduction at the alpha- and beta-positions originate from the medium (H2O) and the pro-4S hydrogen of NADPH, respectively.

引用

页码：355 / 358

页数：4

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