Synthesis of asparagine-linked bacillosamine

摘要

Various types of protein glycosylation have been identified from prokaryotes.Recent investigations have revealed the presence of N-linked glycoproteins in the pathogenic bacterium,Campylobacter jejuni.The structure of this glycan is unique,consisting of 5 GalNAc and 1 Glc,in addition to 2,4-diacetamido-2,4,6-trideoxy-D-glucopyranose(bacillosamine;Bac),which is N-gly-cosidically linked to the side chain of asparagine(Asn).We synthesized Bac from a 2-azido-2-deoxy-D-galactose derivative,which was further converted to the Asn-linked form.