All-transglycolytic synthesis and characterization of sialyl(alpha2-3)galactosyl(beta1-4)xylosyl-p-nitrophenyl(beta1-), an oligosaccharide derivative related to glycosaminoglycan biosynthesis.
Beta-D-Xylopyranosides, such as p-nitrophenyl-beta-D-xylopyranoside (Xyl-Np) or 4-methylumbelliferyl-beta-D-xylopyranoside (Xyl-MeUmb), when added to the culture medium of human skin fibroblasts have previously been shown to produce some Np- or MeUmb-oligosaccharides related to the regulation of glycosaminoglycan biosynthesis. Among these oligosaccharide derivatives, we synthesized the trisaccharide derivative NeuAc(alpha2-3)Gal(beta1-4)Xyl-Np(beta1- as a potential inhibitor of human skin fibroblast glycosaminoglycan biosynthesis. This synthesis was achieved by sequential use of transglycosylating activities of Escherichia coli beta-galactosidase and Trypanosoma cruzi trans-sialidase. The structure of the oligosaccharide obtained was determined by HPLC, ion-spray mass spectrometry, and NMR.
Vetere
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Department of Biochemistry, Biophysics and Macromolecular Chemistry, University of Trieste, Italy. vetere@univ.trieste.it
Ferro
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Bosco
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M
Cescutti
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P
Paoletti
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S
D002236:Carbohydrate Conformation; D002850:Chromatography, Gel; D002851:Chromatography, High Pressure Liquid; D006019:Glycolysis; D006025:Glycosaminoglycans / Q000096:biosynthesis*; D006801:Humans; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009578:Nitrobenzenes / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000378:metabolism; D009844:Oligosaccharides / Q000096:biosynthesis* / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000378:metabolism
D006025:Glycosaminoglycans; D009578:Nitrobenzenes; D009844:Oligosaccharides; C108165:sialyl-2-3-galactosyl-1-4-xylosyl-4-nitrophenyl-1-