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Synthesis and biological activity of alpha-L-fucosyl ceramides, analogues of the potent agonist, alpha-D-galactosyl ceramide KRN7000.

Veerapen N, Reddington F, Bricard G, Porcelli SA, Besra GS - Bioorg. Med. Chem. Lett. (2010)

Bottom Line: Activation of iNKT cells is known to lead to the production of cytokines that can help alleviate or exacerbate these conditions. alpha-Galactosyl ceramide (alpha-GalCer) is a known agonist of iNKT cells and it is believed that its fucosyl counterpart might have similar immunogenic properties.We herein report the synthesis of alpha-L-fucosyl ceramide derivatives and describe their biological evaluation.The key challenge in the synthesis of the target molecules involved the stereoselective synthesis of the alpha-glycosidic linkage.

View Article: PubMed Central - PubMed

Affiliation: School of Biosciences, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK.

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(a) Me2S, 2-Cl-pyridine, Tf2O, CH2Cl2; (b) dimethyl(methylthio)sulfonium triflate (DMTST), CH2Cl2, 0 °C-rt.
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fig2: (a) Me2S, 2-Cl-pyridine, Tf2O, CH2Cl2; (b) dimethyl(methylthio)sulfonium triflate (DMTST), CH2Cl2, 0 °C-rt.

Mentions: Fan et al.25 reported the synthesis of compound 4d, while Okamoto et al.27 reported that of compound 4e. Both groups obtained their target compounds as an α, β mixture (3:1 ratio) from different glycosyl donors and acceptors (Scheme 1). On the other hand, in the original reported synthesis of the fucosylceramide 1, only the α-anomer was isolated when another ceramide acceptor was used under different reaction conditions.


Synthesis and biological activity of alpha-L-fucosyl ceramides, analogues of the potent agonist, alpha-D-galactosyl ceramide KRN7000.

Veerapen N, Reddington F, Bricard G, Porcelli SA, Besra GS - Bioorg. Med. Chem. Lett. (2010)

(a) Me2S, 2-Cl-pyridine, Tf2O, CH2Cl2; (b) dimethyl(methylthio)sulfonium triflate (DMTST), CH2Cl2, 0 °C-rt.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC2957807&req=5

fig2: (a) Me2S, 2-Cl-pyridine, Tf2O, CH2Cl2; (b) dimethyl(methylthio)sulfonium triflate (DMTST), CH2Cl2, 0 °C-rt.
Mentions: Fan et al.25 reported the synthesis of compound 4d, while Okamoto et al.27 reported that of compound 4e. Both groups obtained their target compounds as an α, β mixture (3:1 ratio) from different glycosyl donors and acceptors (Scheme 1). On the other hand, in the original reported synthesis of the fucosylceramide 1, only the α-anomer was isolated when another ceramide acceptor was used under different reaction conditions.

Bottom Line: Activation of iNKT cells is known to lead to the production of cytokines that can help alleviate or exacerbate these conditions. alpha-Galactosyl ceramide (alpha-GalCer) is a known agonist of iNKT cells and it is believed that its fucosyl counterpart might have similar immunogenic properties.We herein report the synthesis of alpha-L-fucosyl ceramide derivatives and describe their biological evaluation.The key challenge in the synthesis of the target molecules involved the stereoselective synthesis of the alpha-glycosidic linkage.

View Article: PubMed Central - PubMed

Affiliation: School of Biosciences, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK.

Show MeSH
Related in: MedlinePlus