Institute for Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163, A-1090, Vienna, Austria.
Bioorg Med Chem Lett. 2011 Oct 15;21(20):6135-8. doi: 10.1016/j.bmcl.2011.08.025. Epub 2011 Aug 12.
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 δ-valerolactones, the jasmine lactones and their ε-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).
Baeyer-Villiger 单加氧酶 (BVMOs) 是一种高效、高选择性的生物催化剂,可通过动力学拆分 2-取代环酮来合成芳族内酯,其中以两种 δ-戊内酯、茉莉内酯及其 ε-己内酯同系物为例。通过分析规模筛选 BVMO 文库,然后进行制备全细胞生物转化,确定了两种非常适合此任务的酶(节杆菌 BP2 的环己酮单加氧酶和 Rhodococcus SC1 的环十二酮单加氧酶):易于获得的外消旋起始原料可被生物氧化成几乎为对映体纯的酮和内酯,收率高(48-74%),光学纯度高(ee 值为 93%至>99%,E 值>100)。