S-Linked Ganglioside Analogues for Use in Conjugate Vaccines

Glycosidase resistant thioglycoside precursors of the melanoma-associated ganglioside GM2 have been synthesized starting from lactose. Syntheses of several analogues of ganglioside GM3 and a positional isomer have been developed. These compounds contain thio-linked sialic acid residues and a modifie...

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Veröffentlicht in:	Organic letters 2004-03, Vol.6 (6), p.897-900
Hauptverfasser:	Rich, Jamie R, Bundle, David R
Format:	Artikel
Sprache:	eng
Schlagworte:	Antibody Formation Antigens, Surface - chemistry Cross Reactions Gangliosides - chemical synthesis Gangliosides - immunology Gangliosides - therapeutic use Melanoma - immunology Melanoma - therapy Molecular Structure Thioglycosides - chemistry Trisaccharides - chemistry Trisaccharides - immunology Vaccines, Conjugate - immunology Vaccines, Conjugate - therapeutic use
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Beschreibung
Zusammenfassung:	Glycosidase resistant thioglycoside precursors of the melanoma-associated ganglioside GM2 have been synthesized starting from lactose. Syntheses of several analogues of ganglioside GM3 and a positional isomer have been developed. These compounds contain thio-linked sialic acid residues and a modified ceramide aglycon functionalized for coupling to proteins, surfaces, or matrices. The hydrolytic stability of these oligosaccharides enhances the immunogenicity of the corresponding conjugate vaccines by ensuring their integrity in the acidic compartments of antigen processing cells.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol036460p