期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 348, 期 4-5, 页码 487-492出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200505342
关键词
biotransformations; catalytic promiscuity; enzyme catalysis; Markovnikov addition; N-heterocycles
Three acylases, including D-aminoacylase from Escherichia coli, acylase Amano from Aspergillus oryzae and immobilized penicillin G acylase from Escherichia coli have been found to possess novel activity to catalyze the Markovnikov addition reaction of N-heterocycles to vinyl esters. The aza-Markovnikov addition reactions of 4-nitroimidazle to vinyl acetate catalyzed by D-aminoacylase, acylase Amano and immobilized penicillin G acylase were up to 1260-fold, 720-fold and 320-fold faster than the respective non-enzymatic reaction. Some control experiments have been designed to demonstrate the catalytic specificity of acylases. Under the catalysis of these promiscuous acylases, a number of N-heterocycles, including some pentacyclic N-heterocycles, pyrimidines and purities, were successfully added to a series of vinyl esters in moderate to excellent yields to prepare N-heterocycle derivatives. The acylase-catalyzed Markovnikov addition reaction has provided a new strategy to perform the Markovnikov addition and expanded the application of biocatalysts.
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