Synthesis of clustered glycoside-antigen conjugates by two one-pot, orthogonal, chemoselective ligation reactions: scope and limitations.
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.
Grandjean
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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
Gras-Masse
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Melnyk
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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
D006027:Glycosides; D000949:Histocompatibility Antigens Class II; D010455:Peptides; D008239:Lysine