title: Synthesis and conformational and NMR studies of alpha-D-mannopyranosyl and alpha-D-mannopyranosyl-(1----2)-alpha-D-mannopyranosyl linked to L-serine and L-threonine.
abstract: alpha-D-Mannopyranosyl and alpha-D-mannopyranosyl-(1----2)-alpha-D- mannopyranosyl linked to L-serine and L-threonine have been synthesised as model substances for the linkage region in certain O-linked glycoproteins. Metropolis Monte Carlo simulations were performed with a modified version of the GESA program, to yield theoretical NOEs and interatomic distances as ensemble-average values, and these were compared with results from steady-state NOE experiments. The NOEs were determined as ensemble-average and as global minimum values. NMR chemical shift differences, obtained for signals of the glycopeptides relative to those of the respective monomers, were interpreted in terms of short inter-residue atomic distances as found within the global minima, and on the basis of averaged distances derived from Monte Carlo simulations.
authors.affiliation: Kabi Pharmacia Therapeutics, Urology/Gynaecology, Stockholm, Sweden.
authors.forename: A
authors.initials: A
authors.lastname: Helander
authors.forename: L
authors.initials: L
authors.lastname: Kenne
authors.forename: S
authors.initials: S
authors.lastname: Oscarson
authors.forename: T
authors.initials: T
authors.lastname: Peters
authors.forename: J R
authors.initials: JR
authors.lastname: Brisson
mesh_terms: D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D003198:Computer Simulation; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose; D008362:Mannosides / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D008969:Molecular Sequence Data; D015394:Molecular Structure; D012694:Serine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013912:Threonine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D007202:Indicators and Reagents; D008362:Mannosides; C077468:O-(2-O-mannopyranosyl-mannopyranosyl)threonine; C077466:O-(2-O-mannopyranosyl-mannopyranosyl)serine; D013912:Threonine; D012694:Serine; C077467:O-mannopyranosylthreonine; C077465:O-mannopyranosylserine; D008358:Mannose