Stereoselective enzymatic galactosylation of C-glucosides

The enzyme β-1,4-galactosyl transferase from bovine colostrum (GalT) is able stereoselectively to galactosylate C-glucosides (i.e. 1 and 4), precursors of stable glycoconjugate analogues, and a systematic investigation of the structural modifications at C-1 and/or C-5 of the glycosides that can be accepted by this enzyme has been undertaken, adding information to the currently accepted model of substrate binding into the GalT active site.

[1]  K. Brew,et al.  Chemical and enzymatic synthesis of glycoconjugates 1. Enzymatic galactosylation of conduritol B , 1995 .

[2]  Sergio Riva,et al.  Role of solvents in the control of enzyme selectivity in organic media , 1995 .

[3]  Y. Nishida,et al.  Xylose: The First Ambident Acceptor Substrate for Galactosyltransferase from Bovine Milk , 1994 .

[4]  T. Lowary,et al.  Recognition of synthetic O-methyl, epimeric, and amino analogues of the acceptor α-L-Fucp-(1 → 2)-β-D-Galp-OR glycosyltransferases☆☆☆ , 1994 .

[5]  S. Riva,et al.  Enzyme-mediated regioselective acylation of polyhydroxylated natural products , 1994 .

[6]  Chi‐Huey Wong,et al.  Enzymatic synthesis of N- and O-linked glycopeptides , 1993 .

[7]  H. Kunz,et al.  Enzymatic glycosylation of O-glycopeptides , 1992 .

[8]  Chi‐Huey Wong,et al.  Probing the acceptor specificity of .beta.-1,4-galactosyltransferase for the development of enzymatic synthesis of novel oligosaccharides , 1991 .

[9]  J. Paulson,et al.  High-efficiency synthesis of sialyloligosaccharides and sialoglycopeptides , 1990 .

[10]  M. Palcic,et al.  Transfer of D-galactosyl groups to 6-O-substituted 2-acetamido-2-deoxy-D-glucose residues by use of bovine D-galactosyltransferase. , 1987, Carbohydrate research.

[11]  T. V. RajanBabu,et al.  1-Methylene sugars as C-glycoside precursors , 1986 .

[12]  L. Berliner,et al.  The lactose synthase acceptor site: a structural map derived from acceptor studies , 1984, Molecular and Cellular Biochemistry.

[13]  E. Davidson,et al.  Specificity of pyruvate kinase. , 1959, Biochimica et biophysica acta.

[14]  S. Riva,et al.  Selective Acylation of 4,6-O-Benzylidene Glycopyranosides by Enzymatic Catalysis , 1993 .

[15]  J. Thiem,et al.  Kombinierte chemoenzymatische Synthese von N‐Glycoproteinbausteinen , 1990 .

[16]  A. Klibanov,et al.  Protease-catalyzed regioselective esterification of sugars and related compounds in anhydrous dimethylformamide , 1988 .

[17]  S. David,et al.  Synthesis with immobilized enzymes of two trisaccharides, one of them active as the determinant of a stage antigen. , 1984 .