Use of the NEO strategy (Nucleophilic addition/Epoxide Opening) for the synthesis of a new C-galactoside ester analogue of KRN 7000.

Aline Banchet-Cadeddu (1) , Agathe Martinez (1) , Stéphane Guillarme (2) , Véronique Parietti (3) , Fanny Monneaux (3) , Eric Hénon (1) , Jean-Hugues Renault (1) , Jean-Marc Nuzillard (1) , Arnaud Haudrechy (1)

1 ICMR - Institut de Chimie Moléculaire de Reims - UMR 7312
2 UCO2M - Unité de chimie organique moléculaire et macromoléculaire
3 ICT - Immunologie et chimie thérapeutiques

Our goal in the search for potentially bioactive analogues of KRN 7000 was to design an easy synthetic approach to a library of analogues using a strategy recently developed in our laboratory based on a Nucleophilic addition followed by an Epoxide Opening (the NEO strategy). Through the use of a common pivotal structure, a new C-galactoside ester analogue (23) was synthesized which showed an encouraging T(H)2 biased response during preliminary biological tests.

Mots clés: α-Galactosylceramide; Ester analogue; NEO strategy; NKT cells

Domaines: Biologie moléculaire

Aline Banchet-Cadeddu, Agathe Martinez, Stéphane Guillarme, Véronique Parietti, Fanny Monneaux, et al.. Use of the NEO strategy (Nucleophilic addition/Epoxide Opening) for the synthesis of a new C-galactoside ester analogue of KRN 7000.. Bioorganic and Medicinal Chemistry Letters, 2011, 21 (8), pp.2510-2514. ⟨10.1016/j.bmcl.2011.02.044⟩. ⟨hal-00579736⟩