Baeyer-Villiger monooxygenases in aroma compound synthesis

被引：27

作者：

Fink, Michael J. ^{[1
]}

Rudroff, Florian ^{[1
]}

Mihovilovic, Marko D. ^{[1
]}

机构：

[1] Vienna Univ Technol, Inst Appl Synthet Chem, A-1090 Vienna, Austria

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2011年 / 21卷 / 20期

关键词：

Fragrance compounds; Mango lactones; Jasmine lactone; Stereoselective synthesis; Kinetic resolution; OXIDATION; KETONES; LACTONES;

D O I：

10.1016/j.bmcl.2011.08.025

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Baeyer-Villiger monooxygenases (BVMOs) are presented as highly selective and efficient biocatalysts for the synthesis of aroma lactones via kinetic resolution of 2-substituted cycloketones, exemplified with two delta-valerolactones, the jasmine lactones and their E-caprolactone homologs. Analytical scale screens of our BVMO library ensued by preparative whole-cell biotransformations led to the identification of two enzymes (cyclohexanone monooxygenase from Arthrobacter BP2 and cyclododecanone monooxygenase from Rhodococcus SC1) perfectly suited for the task at hand: easily accessible racemic starting materials were bio-oxidized to almost enantiopure ketones and lactones in good yields (48-74%) and optical purities (ee 93% to >99%, E>100). (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：6135 / 6138

页数：4

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