Synthesis and biological activity of α-galactosyl ceramide KRN7000 and galactosyl (α1→2) galactosyl ceramide

Synthesis and biological activity of α-galactosyl ceramide KRN7000 and galactosyl (α1→2) galactosyl ceramide
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DOI:
10.1016/j.bmcl.2009.05.095
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发表时间:
2009-08-01
影响因子:
2.7
通讯作者:
Besra, Gurdyal S.
Besra, Gurdyal S.
中科院分区:
医学4区
文献类型:
--
作者:
Veerapen, Natacha;Brigl, Manfred;Besra, Gurdyal S.

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我们在此报告了一种更快且更简便的合成具有生物吸引力的α-半乳糖基神经酰胺(α-GalCer)(称为 KRN7000)及其类似物。更重要的是,使用硅束缚的分子内糖基化反应可以轻松获得二糖基神经酰胺 Gal(α 1 -> 2) GalCer,这已被证明需要摄取和加工成具有生物活性的 α-GalCer 衍生物。 (C) 2009 Elsevier Ltd. 保留所有权利。
We herein report a faster and less cumbersome synthesis of the biologically attractive, alpha-galactosyl ceramide (alpha-GalCer), known as KRN7000, and its analogues. More importantly, the use of a silicon tethered intramolecular glycosylation reaction gave easy access to the diglycosyl ceramide Gal(alpha 1 -> 2) GalCer, which has been shown to require uptake and processing to the biologically active alpha-GalCer derivative. (C) 2009 Elsevier Ltd. All rights reserved.