Synthesis of heterodisaccharide-containing peptides, fragments of actinoidin antibiotics

Abstract

Prototypes corresponding to glycopeptide fragments of actinoidin antibiotics have been synthesized using an L-acosaminyl-D-glucose-containing heterodisaccharide linked to 4-hydroxyphenylglycine as pivotal synthon. This latter compound has been obtained by coupling of a suitably protected D-glucopyranosyl bromide with the blocked amino acid, followed by selective deprotection of the glucopyranosyl moiety at C-2 and subsequent stereospecific attachment of the acosaminyl unit.