A fluorescent derivative of sulfatide, labeled with a dansyl probe at position 6 of galactose, was prepared through a glycosylation reaction between a 6-O-functionalized galactose donor and 3-O-benzoyl-azidosphingosine. The sphingoid acceptor was obtained in high yield through exploitation of a highly stereoselective nucleophilic addition of pentadecyne to 2,3-O-cyclohexylidene-D-glyceraldehyde. The fluorescent sulfatide binds to soluble recombinant human CD1a and is a valuable tool for the study of CD1 antigen binding properties. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
Synthesis of a Fluorescent Sulfatide for the Study of CD1 Antigen Binding Properties / L. Franchini, F. Compostella, A. Donda, L. Mori, D. Colombo, G. De Libero, P. Matto, F. Ronchetti, L. Panza. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2004:23(2004), pp. 4755-4761. [10.1002/ejoc.200400398]
Synthesis of a Fluorescent Sulfatide for the Study of CD1 Antigen Binding Properties
L. FranchiniPrimo
;F. Compostella
;D. Colombo;P. Matto;F. RonchettiPenultimo
;
2004
Abstract
A fluorescent derivative of sulfatide, labeled with a dansyl probe at position 6 of galactose, was prepared through a glycosylation reaction between a 6-O-functionalized galactose donor and 3-O-benzoyl-azidosphingosine. The sphingoid acceptor was obtained in high yield through exploitation of a highly stereoselective nucleophilic addition of pentadecyne to 2,3-O-cyclohexylidene-D-glyceraldehyde. The fluorescent sulfatide binds to soluble recombinant human CD1a and is a valuable tool for the study of CD1 antigen binding properties. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
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