Stereoselective synthesis and immunogenic activity of the C-analogue of sulfatide

Emilia Modica; Federica Compostella; Diego Colombo; Laura Franchini; Marco Cavallari; Lucia Mori; Gennaro De Libero; Luigi Panza; Fiamma Ronchetti

doi:10.1021/ol061100y

Stereoselective synthesis and immunogenic activity of the C-analogue of sulfatide

Org Lett. 2006 Jul 20;8(15):3255-8. doi: 10.1021/ol061100y.

Authors

Emilia Modica¹, Federica Compostella, Diego Colombo, Laura Franchini, Marco Cavallari, Lucia Mori, Gennaro De Libero, Luigi Panza, Fiamma Ronchetti

Affiliation

¹ Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università di Milano, Via Saldini 50, 20133-Milano, Italy, and Experimental Immunology, Department of Research, Basel University Hospital, Hebelstrasse 20, 4031-Basel, Switzerland.

PMID: 16836379
DOI: 10.1021/ol061100y

Abstract

[Structure: see text] The C-sulfatide 1b was synthesized through a [2,3]-Wittig sigmatropic rearrangement and a Horner-Wadsworth-Emmons olefination as the key steps. The C-analogue 1b is less immunogenic than natural sulfatide 1a, but induces a preferential secretion of the proinflammatory cytokine IFN-gamma.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Interferon-gamma / biosynthesis*
Molecular Structure
Stereoisomerism
Structure-Activity Relationship
Sulfoglycosphingolipids / chemical synthesis*
Sulfoglycosphingolipids / immunology*

Substances

Sulfoglycosphingolipids
Interferon-gamma