Synthesis of a glycopeptide with phytoalexin elicitor activity I. Syntheses of a triglycoyl l-serine and a triglycosyl l-seryl-l-proline dipeptide

✍ Scribed by Tadahiro Takeda; Takuya Kanemitsu; Motohiro Ishiguro; Yukio Ogihara; Machiko Matsubara

• Book ID: 102998448
• Publisher: Elsevier Science
• Year: 1994
• Tongue: English
• Weight: 781 KB
• Volume: 256
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(94)84227-2

✦ Synopsis

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.