The nephritogenic glycopeptide from rat glomerular basement membrane: synthesis of α-D-glucopyranosylamine derivatives

Abstract

N-(L-β-aspartyl)-α-D-glucopyranosylamine has been prepared, as a model of a corresponding derivative possibly present in glomerular basement membrane of rats, by the condensation of α-ethyl benzyloxycarbonyl-L-aspartate with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosylamine in the presence of diethylphosphorocyanidate. This was followed by hydrogenolysis, de-O-acetylation, and deethoxylation of the resulting 2,3,4,6-tetra-O-acetyl-N-(α-ethyl benzyloxycarbonyl-L-β-aspartyl)-α-D-glucopyranosylamine to remove the protecting groups. The 13C nmr spectra of the corresponding glycosylamine derivatives are analyzed and discussed.