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Literature DB >> 26028787

A Solvent-free Approach to Glycosyl Amides: Towards the Synthesis of α-N-Galactosyl Ceramides.

Abstract

A new, simple and efficient method for the synthesis of both α- and β-glycosyl amides using solvent-free conditions is described. This method involves the coupling of glycosyl amines with the p-nitrophenol esters of lipids as a key step.

Entities: Chemical Disease Gene Species

Keywords: glycolipids; glycosyl amides; iNKT cells; solvent-free

Year: 2015 PMID： 26028787 PMCID： PMC4445891 DOI： 10.1016/j.tetlet.2015.02.133

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

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References

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A Solvent-free Approach to Glycosyl Amides: Towards the Synthesis of α-N-Galactosyl Ceramides.

1. The first synthesis of a thioglycoside analogue of the immunostimulant KRN7000.

2. The natural killer T cell ligand alpha-galactosylceramide prevents or promotes pristane-induced lupus in mice.

3. Efficient synthesis of alpha-C-galactosyl ceramide immunostimulants: use of ethylene-promoted olefin cross-metathesis.

4. Prevention of diabetes in nonobese diabetic mice mediated by CD1d-restricted nonclassical NKT cells.

5. A new method for the stereoselective synthesis of alpha- and beta-glycosylamines using the Burgess reagent.

6. Up-regulation of CD1d expression restores the immunoregulatory function of NKT cells and prevents autoimmune diabetes in nonobese diabetic mice.

7. The reaction of thio acids with azides: a new mechanism and new synthetic applications.

8. Synthesis of a glycopeptide carrying a N-linked core pentasaccharide.

9. C-Galactosylceramide Diastereomers via Sharpless Asymmetric Epoxidation Chemistry.

Review 10. Stimulation of natural killer T cells by glycolipids.