The chemoenzymatic synthesis of (S)-13-hydroxyoctadeca-(9Z,11E)-dienoic acid using the hydroxynitrile lyase from Hevea brasiliensis

被引：43

作者：

Johnson, DV ^{[1
]}

Griengl, H ^{[1
]}

机构：

[1] GRAZ TECH UNIV,INST ORGAN CHEM,SPEZIALFORSCH BEREICH BIOKATALYSE,A-8010 GRAZ,AUSTRIA

来源：

TETRAHEDRON | 1997年 / 53卷 / 02期

关键词：

D O I：

10.1016/S0040-4020(96)01023-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(S)-13-Hydroxyoctadeca-(9Z, 11E)-dienoic acid (1) was synthesized in nine steps starting from (E)-2-octenal (2). The (S)-hydroxynitrile lyase cloned from Hevea bradiliensis, that has been overexpressed in Pichia pastoris, was used to interconvert 2 into (S)-cyanohydrin 3. The subsequent butyrate 6 was rearranged using the palladium-bis-(acetonitrile)-dichloride to give the unsaturated nitrile 7 which was fully elaborated to the hydroxy acid 1 in an overall 11% yield and with 99% e.e. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：617 / 624

页数：8

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