Solid-phase synthesis of serglycin glycopeptides on a new allyl ester linker

t-Butyl 6-bromo-(E)-4-hexenoate was used as a handle for the solid-phase sy nthesis of glycopeptides. The handle was first conjugated with Fmoc amino a cids to form the allyl esters, which were then attached to the Sieber amide resin via acidic cleavage of the t-butyl esters followed by activation of the liberated carboxylic acids. Solid-phase synthesis was demonstrated for the glycopeptide oligomers modeled after glycosyl Ser-Gly repeating sequenc e of proteoglycan. (C) 2000 Elsevier Science Ltd. All rights reserved.