Chemoselective ligation applied to the synthesis of a biantennary N-linked glycoform of CD52.
We report here a strategy for the synthesis of N-linked glycopeptide analogues that replace the glycosidic linkages extending from the core pentasaccharide with thioethers amenable to construction by chemoselective ligation. The key building block, a pentasaccharide-Asn analogue containing two thiol residues, was incorporated into CD52 by 9-fluorenylmethoxycarbonyl (Fmoc)-based solid-phase peptide synthesis. An undecasaccharide mimetic was then readily generated by alkylation of this glycopeptide with an N-bromoacetamido trisaccharide. The rapid assembly of a complex type N-linked glycopeptide mimetic was accomplished using this technique.
Pratt
Matthew R
MR
Department of Chemistry, University of California, Berkeley 94720, USA.
Bertozzi
Carolyn R
CR
D015703:Antigens, CD / Q000737:chemistry*; D000951:Antigens, Neoplasm / Q000737:chemistry*; D000074301:CD52 Antigen; D002240:Carbohydrate Sequence; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D006023:Glycoproteins / Q000138:chemical synthesis / Q000737:chemistry*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry
D015703:Antigens, CD; D000951:Antigens, Neoplasm; D000074301:CD52 Antigen; D006020:Glycopeptides; D006023:Glycoproteins; D009844:Oligosaccharides