期刊
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
卷 21, 期 20, 页码 6135-6138出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2011.08.025
关键词
Fragrance compounds; Mango lactones; Jasmine lactone; Stereoselective synthesis; Kinetic resolution
资金
- EU [212281]
- Sparkling Science initiative of the Austrian Ministry of Science and Research (BMWF) [SPA/01/2007-52]
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.
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