Synthesis and conformational analysis of the repeating units of bacterial spore peptidoglycan.
Deprotection of the fully blocked disacharide allyl O-(2-amino-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-beta-D-glucopyranosyl-1',2-lactam)-(1-->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranoside by selective de-O-allylation and parallel removal of the benzylidene and O-benzyl groups is described. The resulting beta-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.
Keglević
Dina
D
Rudjer Bosković Institute, P.O. Box 180, Bijenicka 54, HR-10002, Zagreb, Croatia.
Kojić-Prodić
Biserka
B
Tomisić
Zrinka Banić
ZB
D000107:Acetylation; D000117:Acetylglucosamine / Q000031:analogs & derivatives / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006020:Glycopeptides / Q000138:chemical synthesis / Q000737:chemistry; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008969:Molecular Sequence Data; D010457:Peptidoglycan / Q000737:chemistry*; D013171:Spores, Bacterial / Q000737:chemistry*; D014961:X-Ray Diffraction
D006020:Glycopeptides; D010457:Peptidoglycan; D000117:Acetylglucosamine