The nephritogenic glycopeptide from rat glomerular basement membrane. II. Synthesis of O-(.ALPHA.-D-glucopyranosyl)-(1.RAR.6)-O-.BETA.-D-glucopyranosyl-(1.RAR.6)-N-(L-.BETA.-aspartyl)-.ALPHA.-D-glucopyranosylamine (.ALPHA.-D-Glc-(1.RAR.6)-.BETA.-D-Glc-(1.RAR.6)-.ALPHA.-D-Glc-(1.RAR.Asn))
- 1 January 1981
- journal article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 29 (11) , 3196-3201
- https://doi.org/10.1248/cpb.29.3196
Abstract
O-(α-D-Glucopyranosyl)-(1→6)-O-β-D-glucopyranosyl-(1→6)-N-(L-β-aspartyl)-α-D-glucopyranosylamine has been prepared, as a model of a derivative possibly present in the glomerular basement membrane of rats, by condensation of the corresponding trisaccharide α-amine with α-ethyl benzyloxycarbonyl-L-aspartate in the presence of diethylphosphorocyanidate. This was followed by hydrogenolysis, de-O-acetylation, and deethoxylation of the resulting trisaccharide-amino acid linked derivative to remove the protecting groups. The 13C-nuclear magnetic resonance spectra of this product and related glycosylamine derivatives are analyzed and discussed.Keywords
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