Synthesis of α-galactosyl ceramide and the related glycolipids for evaluation of their activities on mouse splenocytes
Resource
Tetrahedron 61 (7): 1855-1862
Journal
Tetrahedron
Journal Volume
61
Journal Issue
7
Pages
1855-1862
Date Issued
2005
Author(s)
Fan, G.-T.
Pan, Y.-S.
Lu, K.-C.
Cheng, Y.-P.
Lin, W.-C.
Lin, S.
Lin, C.-H.
Wong, C.-H.
Lin, C.-C.
Abstract
Phytosphingosine and its short-chain analog were efficiently synthesized with 19% overall yield in 10 steps, respectively, starting from an inexpensive d-lyxose. Galactosyl donors of sulfide and phosphite types bearing benzoyl protecting groups of 4- and 6-OH underwent glycosylation in excellent α-anomeric selectivity. A variety of α-galactosyl, fucosyl and glucosyl ceramides and serine-type lipids were prepared, and their activities involved in the proliferation of mouse splenocytes and the expression of cytokines were elucidated. Besides α-galactosyl ceramides, a galactosyl serine-type lipid also exhibited substantial effect on the expression of cytokines IFN-γ and IL-4. © 2004 Elsevier Ltd. All rights reserved.
Type
journal article
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