Direct Access to Medium-Chain α,ω-Dicarboxylic Acids by Using a Baeyer-Villiger Monooxygenase of Abnormal Regioselectivity

Chembiochem : a European Journal of Chemical Biology
Jia-Mei YuJian-He Xu

Abstract

Baeyer-Villiger monooxygenases (BVMOs) are versatile biocatalysts in organic synthesis that can generate esters or lactones by inserting a single oxygen atom adjacent to a carbonyl moiety. The regioselectivity of BVMOs is essential in determining the ratio of two regioisomers for converting asymmetric ketones. Herein, we report a novel BVMO from Pseudomonas aeruginosa (PaBVMO); this has been exploited for the direct synthesis of medium-chain α,ω-dicarboxylic acids through a Baeyer-Villiger oxidation-hydrolysis cascade. PaBVMO displayed the highest abnormal regioselectivity toward a variety of long-chain aliphatic keto acids (C16 -C20 ) to date, affording dicarboxylic monoesters with a ratio of up to 95 %. Upon chemical hydrolysis, α,ω-dicarboxylic acids and fatty alcohols are readily obtained without further treatment; this significantly reduces the synthetic steps of α,ω-dicarboxylic acids from renewable oils and fats.

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Citations

Nov 9, 2019·Nature Communications·Shuke WuThomas R Ward
Nov 19, 2020·Chembiochem : a European Journal of Chemical Biology·Guang-Xiang ZhangChun-Xiu Li
Jan 3, 2021·Biochemical and Biophysical Research Communications·Qi-Fan SunJiang Pan

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