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PubMed1977

Characterization of the chondroitin sulfate produced by B16 mouse melanoma cells.

The mucopolysaccharides produced by B16 mouse melanoma cells have been isolated in milligram quantities from the spent media in which the cells were grown in the presence of 2-amino-2-deoxy-D-glucose-t and [35S]-sulfate. The mucopolysaccharides obtained by precipitation with cetylpyridinium chloride from the Pronase digest of the media were further purified by gel filtration, ion-exchange chromatography, and treatment with nucleases. The major components were identified as chondroitin-4-sulfates by identification of the hexosamine as 2-amino-2-deoxy-D-galactose, and by digestibility with hyaluronidases, chondroitinase AC, and chondro-4-sulfatase. The o.r.d. curve and i.r. spectra of these components also confirmed their similarity to chondroitin-4-sulfate from cartilage. The molecular weight of the polysaccharide chains was estimated to be in the range 90,000-120,000 by sedimentation equilibrium analysis.

Carbohydrates↗
PubMed1975

Four isomeric ethyl 1-thioglycosides from 2-amino-2-deoxy-D-arabinose.

Ethyl 2-amino-2-deoxy-1-thio-alpha- and -beta-D-arabinopyranoside (2 and 4) were obtained by direct ethanethiolation of 2-amino-2-deoxy-D-arabinose (1), and their structures were determined by mass and p.m.r. spectrometry. Ethyl 2-amino-2-deoxy-1-thio-alpha- and -beta-D-arabinofuranoside (11 and 13) were prepared by partial demercaptalation of 2-amino-2-deoxy-D-arabinose diethyl dithioacetal (6) with mercuric chloride (or, preferably, with bromine), with or without protection of the 5-hydroxyl group. Demercaptalation with mercuric chloride gave the beta-D anomers almost exclusively, and treatment with bromine gave a mixture of the alpha and beta anomer in the ratio of similar to 1:1. Alternatively, direct ethanethiolation of 1 in trifluoracetic acid yielded the alpha-D anomer. The structures of 11 and 13 were determined by mass spectrometry, by direct comparison of their N-acetyl derivatives with an authentic enantiomorph (15b), and by p.m.r. spectroscopy. The physicochemical properties of the four 1-thioglycosides (2,4,11, and 13) were compared with those of the O-GLYCOSIDES of D-arabinose.

Amino Sugars↗