Premium
Promiscuous Zinc‐Dependent Acylase‐Mediated One‐Pot Synthesis of Monosaccharide‐Containing Pyrimidine Derivatives in Organic Medium
Author(s) -
Wu Qi,
Xu JianMing,
Xia Li,
Wang JunLiang,
Lin XianFu
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900161
Subject(s) - chemistry , michael reaction , pyrimidine , acylation , catalysis , zinc , monosaccharide , acrylate , organic chemistry , biotransformation , enzyme , organic synthesis , one pot synthesis , combinatorial chemistry , stereochemistry , copolymer , polymer
A facile one‐pot synthesis route to monosaccharide‐containing pyrimidine derivatives was developed by combining the two types of catalytic activities of one enzyme in an organic medium, i.e., the Michael addition/acylation activities of zinc‐dependent D ‐aminoacylase (DA) from Escherichia coli . First, the stepwise approach was investigated. DA showed higher activity towards the Michael addition than acylation in this reaction system. The enzymatic Michael additions of pyrimidines to vinyl acrylate proceeded very rapidly and the initial reaction rates for the Michael addition of pyrimidines to vinyl acrylate were 7.2–16.5 mM min −1 . The catalytic specificity of aminoacylases toward Michael addition was demonstrated by the combination of different control experiments. Then, the two steps could be performed in one pot and a single aminoacylase catalyzed one‐pot biotransformation was constructed. Using this strategy, a series of saccharide‐pyrimidine complexes with potentially biological and pharmacological applications was prepared efficiently. This high Michael addition activity of zinc‐dependent aminoacylases and the novel single aminoacylase‐catalyzed one‐pot synthesis combining two catalytic activities in vitro is of practical significance in expanding the application of enzymes and in the evolution of new biocatalysts.