Solid-phase synthesis of O-linked glycopeptide analogues of enkephalin

SA Mitchell, MR Pratt, VJ Hruby…

Index: Mitchell; Pratt; Hruby; Polt Journal of Organic Chemistry, 2001 ,  vol. 66,  # 7  p. 2327 - 2342

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Citation Number: 126

Abstract

The synthesis of 18 N-α-FMOC-amino acid glycosides for solid-phase glycopeptide assembly is reported. The glycosides were synthesized either from the corresponding O'Donnell Schiff bases or from N-α-FMOC-amino protected serine or threonine and the appropriate glycosyl bromide using Hanessian's modification of the Koenigs-Knorr reaction. Reaction rates of d-glycosyl bromides (eg, acetobromoglucose) with the l-and d-forms of ...