Tetrahedron: Asymmetry

Novel ester linked glycosyl amino acids: convenient building blocks for the synthesis of glycopeptide libraries

RJ Tennant-Eyles, AJ Fairbanks

Index: Tennant-Eyles, Richard J.; Fairbanks, Antony J. Tetrahedron Asymmetry, 1999 , vol. 10, # 2 p. 391 - 401

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Citation Number: 27

Abstract

The completely orthogonally protected aspartic acid derivative FmocAsp (OBn) OtBu is readily synthesized on a large scale. Deprotection of the β-carboxylic acid allows coupling to various sugar derivatives via free hydroxyl groups to produce novel glycosyl amino acids. Subsequent deprotection of either the α-acid or nitrogen is achieved cleanly to allow elaboration into an oligopeptide, whilst selective deprotection of PMB protected sugar ...