title: Synthesis of clustered glycoside-antigen conjugates by two one-pot, orthogonal, chemoselective ligation reactions: scope and limitations.
abstract: Major histocompatibility class II antigens have been bound to clustered glycosides for selective targeting of the dendritic cell mannose receptor. Di-, tetra-, and octavalent glycoside-antigen conjugates have been obtained after two, orthogonal, hydrazone/thioether ligations, performed by using thio derivatives of D-mannose, D-galactose, or D(-)-quinic acid, glyoxylyl (or hydrazino)-N-chloroacetylated lysinyl trees, and N-terminal hydrazino (or glyoxylyl) peptide antigens. Successful one-pot condensations have been developed to account for the nature of the antigens and the valency of the trees.
authors.affiliation: Laboratoire de Synthèse, Structure et Fonction des Biomolécules, UMR 8525 du CNRS, Université de Lille II, Institut de Biologie et Institut Pasteur de Lille 1, France. Cyrille.Grandjean@pasteur-lille.fr
authors.forename: C
authors.initials: C
authors.lastname: Grandjean
authors.forename: H
authors.initials: H
authors.lastname: Gras-Masse
authors.forename: O
authors.initials: O
authors.lastname: Melnyk
mesh_terms: D000595:Amino Acid Sequence; D002851:Chromatography, High Pressure Liquid; D006027:Glycosides / Q000737:chemistry*; D000949:Histocompatibility Antigens Class II / Q000737:chemistry*; D008239:Lysine / Q000737:chemistry; D008968:Molecular Conformation; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis
chemical_list: D006027:Glycosides; D000949:Histocompatibility Antigens Class II; D010455:Peptides; D008239:Lysine