The nephritogenic glycopeptide from rat glomerular basement membrane. X. Synthesis of an N-triglycosyl dipeptide and characteristics of its cis-trans isomers.
Isomers of O-alpha-D-glucopyranosyl-(1----6)-O-beta-D-glucopyranosyl- (1----6)-N-[L-aspart-1-oyl-(L-proline)-4-oyl]-alpha-D-glucopyranos ylamine have been prepared, as models for a derivative possibly present in the glomerular basement membrane of rats, by condensation of the corresponding dipeptide derivative (5) with triglycosylamine (4) in the presence of O,O-diethylcyanophosphonate, followed by deprotection of the trisaccharide-dipeptide derivative. During the deprotection process, cis- and trans-isomers containing proline were separated by silica gel column chromatography and also reversed-phase high performance liquid chromatography.
Takeda
T
T
Faculty of Pharmaceutical Sciences, Nagoya City University, Japan.
Kojima
K
K
Ogihara
Y
Y
D000595:Amino Acid Sequence; D000818:Animals; D001485:Basement Membrane / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D006023:Glycoproteins / Q000138:chemical synthesis* / Q000302:isolation & purification; D007536:Isomerism; D007678:Kidney Glomerulus / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D051381:Rats
D006023:Glycoproteins; C015382:nephritogenoside