Synthesis of a glycopeptide with phytoalexin elicitor activity. I. Synthesis of a triglycosyl L-serine and a triglycosyl L-seryl-L-proline dipeptide.
A stereocontrolled synthesis of the model compound for the phytoalexin elicitor-active glycoprotein is described. Glycosylation of the disaccharide, 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl-(1-->6)-2,3,4-tri-O-acetyl- alpha- D-mannopyranosyl trichloroacetimidate, with N-(carbobenzoxy)-(2,3,4-tri-O-acetyl-alpha-D-mannopyranosyl)-(1-->3)-L- serine methyl ester or N-(carbobenzoxy)-(2,3,4-tri-O-acetyl-alpha-D-mannopyranosyl)-(1-->3)-L- seryl-L- proline methyl ester by use of AgOTf gave the desired trisaccharide-serine or trisaccharide-seryl-proline derivatives, which were transformed into beta-D-glucopyranosyl-(1-->6)-alpha-D-mannopyranosyl-(1-->6)-alpha-D- mannopyranosyl-(1-->3)-L-serine and triglycosyl-(1-->3)-L-seryl-L-proline via removal of the N-carbobenzoxy group, followed by deacylation.
Takeda
T
T
Faculty of Pharmaceutical Sciences, Nagoya City University, Japan.
Kanemitsu
T
T
Ishiguro
M
M
Ogihara
Y
Y
Matsubara
M
M
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000494:pharmacology; D006031:Glycosylation; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009904:Optical Rotation; D010936:Plant Extracts; D011392:Proline; D012694:Serine; D012717:Sesquiterpenes; D013237:Stereoisomerism; D013729:Terpenes; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D000094162:Phytoalexins
D004187:Disaccharides; D006020:Glycopeptides; D007202:Indicators and Reagents; D010936:Plant Extracts; D012717:Sesquiterpenes; D013729:Terpenes; D014312:Trisaccharides; D012694:Serine; D011392:Proline; D000094162:Phytoalexins