Asymmetric whole-cell bioreduction of an α,β-unsaturated aldehyde (citral):: competing prim-alcohol dehydrogenase and C-C lyase activities

被引：61

作者：

Hall, Melanie

Hauer, Bernhard

Stuermer, Rainer

Kroutil, Wolfgang

Faber, Kurt

机构：

[1] Graz Univ, Dept Chem Organ & Bioorgan Chem, A-8010 Graz, Austria

[2] BASF AG, D-67056 Ludwigshafen, Germany

来源：

TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 21期

关键词：

D O I：

10.1016/j.tetasy.2006.11.018

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Asymmetric bioreduction of (E/Z)-3,7-dimethyl-2,6-octadienal (citral) using the enoate reductase activity of whole cells of yeasts, bacteria and fungi, gave the alpha,beta-saturated aldehyde (R)-3,7-dimethyl-6-octenal (citronellal), which constitutes an important flavour component, in up to >= 95% ee. Depending on the microorganism, various amounts of prim-alcohols (nerol/geraniol and citronellol) were formed due to the action of competing prim-alcohol dehydrogenases. Citral lyase activity-leading to the loss of a C-2-fragment (acetaidehyde) forming sulcatone-and oxidation of the aldehyde moiety yielding the carboxylic acid (geranic/neric acid) were detected as additional metabolic activities. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：3058 / 3062

页数：5

共 29 条

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