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Galactosylation by use of β-galactosidase: Enzymatic syntheses of disaccharide nucleosides

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
6
Issue
7
Identifiers
DOI: 10.1016/0957-4166(95)00216-c
Disciplines
  • Biology
  • Chemistry

Abstract

Abstract The synthesis of various galactose containing disaccharide nucleosides has been achieved by utilizing the transgalactosylation potential of ß-galactosidase from Aspergillus oryzae. Thus, using p-nitrophenyl-ß-D-galactoside 1 as galactosyl donor, 2-deoxyuridine 2a, uridine 2b, thymidine 2c and adenosine 2d have proven to be useful acceptors for the enzyme catalyzed disaccharide nucleoside formation. The regiochemistry of the products 4a – 4d formed after acetylation has been assigned unambiguously by using modern NMR-techniques.

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