Enzyme-Catalyzed Hydrolysis of Bicycloheptane and Cyclobutene Diesters to Monoesters

Autor:	Matthew R. Hickey, Bharat P. Patel, Zhiwei Guo, Michael Kwok Y. Wong, Xinhua Qian, Animesh Goswami
Rok vydání:	2013
Předmět:	Cyclobutene Bicyclic molecule biology Organic Chemistry biology.organism_classification Esterase Hydrolysis chemistry.chemical_compound Burkholderia chemistry Yield (chemistry) biology.protein Organic chemistry Candida antarctica Physical and Theoretical Chemistry Lipase
Zdroj:	Organic Process Research & Development. 18:774-780
ISSN:	1520-586X 1083-6160
DOI:	10.1021/op400254c
Popis:	Diacid formation is a major problem in the conventional chemical hydrolysis of a diester to a monoester. Enzyme-catalyzed hydrolysis of dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate (1) by lipases from Candida antarctica and Burkholderia cepacia gave the corresponding monoester 4-(methoxycarbonyl)bicyclo[2.2.1]heptane-1-carboxylic acid (2) in excellent yields with negligible amounts of diacid 3. About 100 kg of monoester 2 was prepared in 78% yield by hydrolysis of diester 1 with a commercially available lipase from B. cepacia. A more efficient process for the hydrolysis of 1 that give monoester 2 in 82% yield was subsequently developed using significantly lower amounts of the commercially available immobilized lipase B from C. antarctica. The commercially available immobilized lipase B from C. antarctica and porcine liver esterase were also efficient for the selective hydrolysis of dimethyl cyclobut-1-ene-1,2-dicarboxylate (4) to the corresponding monoester 5 in yields of 78% and 87%, respectively.
Databáze:	OpenAIRE
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