Abstract
Glycopeptides and glycoproteins have received much attention due to their biological interests in cell recognition and cell adhesion.Recently we have developed a new chemo-enzymatic synthetic strategy for glycopeptide and glycoprotein. In this article we describe our new methodology including 1) a new synthetic method of glycosylasparagine derivatives by the reaction of glycosyl azide and aspartic acid in the presence of tertially phosphine, 2) solid-phase synthesis of [Asn (G1cNAc)] -peptide without protecting the hydroxyl functions using dimethylphosphinothioic mixed anhydride method, 3) peptide elongation by peptide thioester method, and 4) transglycosylation reaction using endo-β-N-acetylglucosaminidase from Mucor hiemalis (Endo-M). By these methods, we synthesized eel calcitonin (32 amino acids) analog having natural complex-type sugar chain (11 sugar residues).
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