title: Pentafluoropropionyl and trifluoroacetyl groups for temporary hydroxyl group protection in oligomannoside synthesis.
abstract: Pentafluoropropionyl (PFP) and trifluoroacetyl (TFA) esters were demonstrated to be useful in facile oligosaccharide synthesis. These were well compatible with glycosylation conditions and removable by treatment with pyridine-EtOH, with complete preservation of acetyl groups. Analytically pure products were obtained quantitatively, simply by evaporating the reaction mixtures. Using O-PFP and O-TFA carrying glycosyl halides, trisaccharide (Manalpha1-->2Manalpha1-->2Man) and tetrasaccharide (Glcalpha1-->3Manalpha1-->2Manalpha1-->2Man) portions of monoglucosylated high-mannose type dodecasaccharide (Glc(1)Man(9)GlcNAc(2)), a putative ligand for the ER chaperon, calnexin and calreticulin, were synthesized.
authors.affiliation: RIKEN (The Institute of Physical and Chemical Research), 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan.
authors.forename: Maki
authors.initials: M
authors.lastname: Takatani
authors.forename: Ichiro
authors.initials: I
authors.lastname: Matsuo
authors.forename: Yukishige
authors.initials: Y
authors.lastname: Ito
mesh_terms: D002240:Carbohydrate Sequence; D000431:Ethanol / Q000737:chemistry; D005466:Fluorocarbons / Q000032:analysis / Q000138:chemical synthesis*; D006031:Glycosylation; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008968:Molecular Conformation; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry; D014269:Trifluoroacetic Acid / Q000032:analysis / Q000138:chemical synthesis*
chemical_list: D005466:Fluorocarbons; D008024:Ligands; D009844:Oligosaccharides; D011725:Pyridines; C028569:oligomannoside; D000431:Ethanol; C033093:perfluoropropionic acid; D014269:Trifluoroacetic Acid; C023666:pyridine