title: Experimental observations on the regioselectivity of glycosylation of a 4,6-diol system in the β-D-mannopyranosyl unit of a N-glycan pentasaccharide core structure.
abstract: The regioselectivity of glycosylation of a 4,6-diol system in the β-mannopyranosyl unit of a N-glycan pentasaccharide core structure is found to be strongly dependent on the structure of the glycosyl donor. While glycosylation with a 2-O-acetyl-D-mannopyranosyl trichloroacetimidate and with a d-mannopyranosyl (α1→3) 2-O-acetyl mannopyranosyl trichoroacetimidate regioselectively occurs at the primary OH-6 position, reaction with d-mannopyranosyl (α1→6) mannopyranosyl 2-O-benzoyl, 2-O-acetyl and 2-O-pivaloyl trichloroacetimidate results in approximately 1:1 mixture of regioisomers at primary OH-6 and secondary OH-4 positions.
authors.affiliation: Biofunctional Nanomaterials Unit, CIC biomaGUNE, Paseo Miramón 182, 20009 San Sebastián, Spain.
authors.forename: Nerea
authors.initials: N
authors.lastname: Ruiz
authors.forename: Sandra S
authors.initials: SS
authors.lastname: Ferreira
authors.forename: Daniel
authors.initials: D
authors.lastname: Padro
authors.forename: Niels-C
authors.initials: NC
authors.lastname: Reichardt
authors.forename: Manuel
authors.initials: M
authors.lastname: Martín-Lomas
mesh_terms: D000081:Acetamides; D000438:Alcohols / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis*; D002236:Carbohydrate Conformation; D062845:Chloroacetates; D006031:Glycosylation; D008358:Mannose / Q000737:chemistry; D009844:Oligosaccharides / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014238:Trichloroacetic Acid / Q000737:chemistry
chemical_list: D000081:Acetamides; D000438:Alcohols; D001688:Biological Products; D062845:Chloroacetates; D009844:Oligosaccharides; D014238:Trichloroacetic Acid; C009528:trichloroacetamide; D008358:Mannose