Enzymatic synthesis and characterization of 6-O-Beta-D-xylopyranosyl-2-acetamido-2-deoxy-D-glucopyranose, a structural analog of primeverose.
The synthesis of the disaccharide 6-O-beta-D-xylopyranosyl-2-acetamido-2-deoxy-D-glucopyranose (N-acetylprimeverosamine), structurally related to the natural disaccharide 6-O-beta-D-xylopyranosyl-D-glycopyranose (primeverose), was obtained via a transglycosylation reaction catalyzed by a crude preparation of beta-D-xylosidase from Aspergillus niger, using p-nitrophenyl beta-D-xylopyranoside as the donor and 2-acetamido-2-deoxy-D-glucopyranose as the acceptor. The yield of the reaction was 36% on a molar basis with respect to the donor. The chemical identity of the product was assessed by HPLC, ionspray mass spectrometry and NMR spectroscopy.
Vetere
A
A
Department of Biochemistry, Biophysics and Macromolecular Chemistry, University of Trieste, Italy. vetere@bbcm.univ.trieste.it
Bosco
M
M
Paoletti
S
S
D001234:Aspergillus niger / Q000201:enzymology*; D004187:Disaccharides / Q000096:biosynthesis* / Q000737:chemistry; D006031:Glycosylation; D014995:Xylosidases / Q000737:chemistry
D004187:Disaccharides; C115906:N-acetylprimeverosamine; D014995:Xylosidases; C026579:exo-1,4-beta-D-xylosidase