title: Facile synthesis of arabinomannose penta- and decasaccharide fragments of the lipoarabinomannan of the equine pathogen, Rhodococcus equi.
abstract: Pentasaccharide repeating unit 20 of the lipoarabinomannan from the equine pathogen, Rhodococcus equi, and its dimer 31, were synthesized. The pentasaccharide was obtained by assembling a benzoylated 2,6-branched mannosyl trisaccharide acceptor 13 with a free hydroxyl group at C-2' of the mannose residue attached to the core mannose residue by (1 --> 6)-linkage, followed by coupling with 2,3,5-tri-O-benzoyl-alpha-D-arabinofuranosyl-(1 --> 2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate (18), and by deacylation. Meanwhile, the decamer 31 was obtained by firstly preparing a benzoylated mannose (1 --> 6)-linked tetrasaccharide backbone 26 with 2-, 2"-O-ClAc, and 2'-, 2'''-O-Ac groups, respectively, then by dechloroacetylation and subsequent condensation with perbenzoylated trichloroacetimidate, and then by deacetylation and subsequent coupling with 18, and finally, by deacylation.
authors.affiliation: Research Center for Eco-Environmental Sciences, Academia Sinica, PO Box 2871, Beijing 100085, PR China.
authors.forename: Zuchao
authors.initials: Z
authors.lastname: Ma
authors.forename: Jianjun
authors.initials: J
authors.lastname: Zhang
authors.forename: Fanzuo
authors.initials: F
authors.lastname: Kong
mesh_terms: D000081:Acetamides; D000818:Animals; D002240:Carbohydrate Sequence; D062845:Chloroacetates; D006031:Glycosylation; D006736:Horses / Q000382:microbiology; D008070:Lipopolysaccharides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008351:Mannans / Q000138:chemical synthesis* / Q000737:chemistry; D008358:Mannose / Q000737:chemistry; D008956:Models, Chemical; D008969:Molecular Sequence Data; D011134:Polysaccharides / Q000737:chemistry*; D016929:Rhodococcus equi / Q000378:metabolism*; D013237:Stereoisomerism; D014238:Trichloroacetic Acid / Q000737:chemistry
chemical_list: D000081:Acetamides; D062845:Chloroacetates; D008070:Lipopolysaccharides; D008351:Mannans; D011134:Polysaccharides; C050016:lipoarabinomannan; C012189:arabinomannan; D014238:Trichloroacetic Acid; C009528:trichloroacetamide; D008358:Mannose