Synthesis of octyl O- and S-glycosides related to the GPI anchor of Trypanosoma brucei and their in vitro galactosylation by trypanosomal alpha-galactosyltransferases.
Octyl O- and S-glycosides of mono- to tri-saccharides related to the core structure alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->6)-alpha-D-Manp of the GPI anchor of Trypanosoma brucei have been prepared via regioselective protodesilylation and glycodesilylation of octyl O- and S-glycosides of 2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1, 3-diyl)-alpha-D-mannopyranoside. The synthetic saccharides have been used as substrates for enzymatic alpha-galactosylation with membrane fractions of bloodstream forms of T. brucei strain 427 variants MITat 1.4, MITat 1.2, and MITat 1.5, respectively.
Ziegler
T
T
Institute of Organic Chemistry, University of Cologne, Germany.
Dettmann
R
R
Duszenko
M
M
Kolb
V
V
D000818:Animals; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002855:Chromatography, Thin Layer; D005700:Galactosyltransferases / Q000378:metabolism*; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry; D017261:Glycosylphosphatidylinositols / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008361:Mannosidases / Q000378:metabolism; D008362:Mannosides / Q000138:chemical synthesis / Q000378:metabolism; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D014346:Trypanosoma brucei brucei / Q000737:chemistry* / Q000201:enzymology*; D000519:alpha-Galactosidase / Q000378:metabolism; D043323:alpha-Mannosidase; D001616:beta-Galactosidase / Q000378:metabolism
D006027:Glycosides; D017261:Glycosylphosphatidylinositols; D008362:Mannosides; D009844:Oligosaccharides; D005700:Galactosyltransferases; D008361:Mannosidases; D000519:alpha-Galactosidase; D001616:beta-Galactosidase; D043323:alpha-Mannosidase