ENZYMATIC-SYNTHESIS AND CHARACTERIZATION OF YLOPYRANOSYL-2-ACETALMIDO-2-DEOXY-D-GLUCOPYRANOSE, A STRUCTURAL ANALOG OF PRIMEVEROSE

The synthesis of the disaccharide -xylopyranosyl-2-acetamido-2-deoxy-D -glucopyranose (N-acetylprimeverosamine), structurally related to the natural disaccharide 6-O-beta-D-xylopyranosyl-D-glucopyranose (primeve rose), was obtained via a transglycosylation reaction catalyzed by a c rude 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 spec troscopy. (C) 1998 Elsevier Science Ltd. All rights reserved.