title: Synthesis of 2-acetamido-2-deoxyglucosylasparagine glyco-tripeptides and -pentapeptides by selective C- and N-terminal elongation of the peptide chain.
abstract: The synthesis of protected 2-acetamido-2-deoxyglucosylasparagine glycopeptides, using the allyl ester as the C-terminal protecting group, their deprotection, and some possible applications of these glycopeptides for the synthesis of modified silica gels and the construction of liposomes are described. The selective carboxyl deblocking is achieved under neutral conditions by rhodium(I)-catalyzed isomerization of the allyl group followed by hydrolysis of the resulting propenyl ester. The tert-butoxycarbonyl group can be cleaved selectively in the presence of the allyl ester with hydrogen chloride in ether. The allyl ester and the acetates can be removed simultaneously with ammonia in methanol. This method opens up a preparative route to glycopeptide model structures of biological interest.
authors.affiliation: Institut für Organische Chemie, Johannes Gutenberg Universität Mainz, F.R.G.
authors.forename: H
authors.initials: H
authors.lastname: Waldmann
authors.forename: J
authors.initials: J
authors.lastname: März
authors.forename: H
authors.initials: H
authors.lastname: Kunz
mesh_terms: D000577:Amides / Q000138:chemical synthesis; D000595:Amino Acid Sequence; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D004151:Dipeptides / Q000138:chemical synthesis; D004952:Esters / Q000138:chemical synthesis; D005782:Gels; D006020:Glycopeptides / Q000138:chemical synthesis*; D008081:Liposomes; D008969:Molecular Sequence Data; D009842:Oligopeptides / Q000138:chemical synthesis*; D058428:Silica Gel; D012822:Silicon Dioxide
chemical_list: D000577:Amides; D004151:Dipeptides; D004952:Esters; D005782:Gels; D006020:Glycopeptides; D008081:Liposomes; D009842:Oligopeptides; D058428:Silica Gel; D012822:Silicon Dioxide