Enzymatic synthesis and characterization of 6-O-β-d-xylopyranosyl-2-acetamido-2-deoxy-d-glucopyranose, a structural analog of primeverose

The synthesis of the disaccharide 6-O-β-d-xylopyranosyl-2-acetamido-2-deoxy-d-glucopyranose (N-acetylprimeverosamine), structurally related to the natural disaccharide 6-O-β-d-xylopyranosyl-d-glucopyranose (primeverose), was obtained via a transglycosylation reaction catalyzed by a crude preparation of β-d-xylosidase from Aspergillus niger, using p-nitrophenyl β-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.