Synthesis and conformational analysis of the repeating units of bacterial spore peptidoglycan Original Research Article

Deprotection of the fully blocked disacharide allyl O-(2-amino-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-β-d-glucopyranosyl-1′,2-lactam)-(1→4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-d-glucopyranoside by selective de-O-allylation and parallel removal of the benzylidene and O-benzyl groups is described. The resulting β-muramyl lactam-(1→4)-GlcNAc disaccharide is characterised as the per-O-acetylated derivative by 1H and 13C NMR spectroscopy and X-ray structure analysis. Conformational analysis about glycosidic bond of repeating units of bacterial spore cortex is based on experimental data and molecular modelling.