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Direct Access to Medium‐Chain α,ω‐Dicarboxylic Acids by Using a Baeyer–Villiger Monooxygenase of Abnormal Regioselectivity
Author(s) -
Yu JiaMei,
Liu YuanYang,
Zheng YuCong,
Li Hao,
Zhang XiaoYan,
Zheng GaoWei,
Li ChunXiu,
Bai YunPeng,
Xu JianHe
Publication year - 2018
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201800318
Subject(s) - regioselectivity , chemistry , moiety , hydrolysis , dicarboxylic acid , structural isomer , monooxygenase , organic chemistry , biocatalysis , baeyer–villiger oxidation , stereochemistry , catalysis , enzyme , reaction mechanism , cytochrome p450
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 ( Pa BVMO); this has been exploited for the direct synthesis of medium‐chain α,ω‐dicarboxylic acids through a Baeyer–Villiger oxidation–hydrolysis cascade. Pa BVMO displayed the highest abnormal regioselectivity toward a variety of long‐chain aliphatic keto acids (C 16 –C 20 ) 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.