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Updated: Mar 29, 2026

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
Published on: May 27, 2015
Synthesis and Activity of 6″-Deoxy-6″-thio-α-GalCer and Peptide Conjugates
Benjamin J Compton1, Ching-wen Tang2, Karen A Johnston1
1The Ferrier Research Institute, Victoria University of Wellington , P.O. Box 600, Wellington 6140, New Zealand.
Abstract:
A major challenge in the development of highly defined synthetic vaccines is the codelivery of vaccine components (i.e., antigen and adjuvant) to secondary lymphoid tissue to induce optimal immune responses. This problem can be addressed by synthesizing vaccines that comprise peptide antigens covalently attached to glycolipid adjuvants through biologically cleavable linkers. Toward this, a strategy utilizing previously unreported 6″-deoxy-6″-thio analogues of α-GalCer that can undergo chemoselective conjugation with peptide antigens is described. Administration of these conjugate vaccines leads to enhanced priming of antigen specific T cells. This simple vaccine design is broadly applicable to multiple disease indications such as cancer and infectious disease.
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