Synthesis of beta-D-Galf-(1-3)-D-GlcNAc by the trichloroacetamidate method and of beta-D-Galf-(1-6)-D-GlcNAc by SnCl4-promoted glycosylation.
In a continuation of our studies on the characterization of the glycoproteins of T. cruzi new galactofuranosyl disaccharides were synthesized. Beta-D-Galf-(1-3)-D-GlcNAc was prepared by employing the trichloroacetamidate procedure for the glycosylation step. The mild conditions of this reaction are appropriate for condensation of 2,3,5,6-tetra-O-benzoyl-beta-D-galactofuranosyl trichloroacetamidate with acid-labile benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-alpha-D-glucopyranoside. On the other hand, tin(IV) chloride promoted condensation of benzyl 2-acetamido-3-O-benzoyl-2-deoxy-alpha-D-glucopyranoside with penta-O-benzoyl-alpha-beta-D-galactofuranose gave the derivative of beta-D-Galf-(1-6)-D-GlcNAc in 78% yield.
Gallo-Rodriguez
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Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina.
Gandolfi
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de Lederkremer
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RM
D000818:Animals; D002384:Catalysis; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D009077:Mucins / Q000737:chemistry; D017971:Tin Compounds; D014349:Trypanosoma cruzi / Q000737:chemistry
D004187:Disaccharides; D009077:Mucins; D017971:Tin Compounds; C410448:galactofuranosyl-1-3-N-acetylglucosamine; C410449:galactofuranosyl-1-6-N-acetylglucosamine; C041694:stannic chloride