通过羰基的膦酯化合成黄苷 2-磷酸二酯。

Synthesis of xanthosine 2-phosphate diesters via phosphitylation of the carbonyl group.

机构信息

Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Japan; Center for Highly Advanced Integration of Nano and Life Sciences, Gifu University (G-CHAIN), Japan; Institute for Glyco-core Research (iGCORE), Gifu University 1-1 Yanagido, Gifu 501-1193, Japan.

Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Japan.

出版信息

Bioorg Med Chem Lett. 2021 Dec 15;54:128439. doi: 10.1016/j.bmcl.2021.128439. Epub 2021 Nov 5.

DOI:10.1016/j.bmcl.2021.128439

PMID:34748937

Abstract

O-Phosphodiesterification of xanthosine has been achieved by a one-pot procedure consisting of the phosphitylation of the 2-carbonyl group of appropriately protected xanthosine derivatives using phosphoramidites and N-(cyanomethyl)dimethylammonium triflate (CMMT), oxidation of the resulting xanthosine 2-phosphite triesters, and deprotection. In addition, a study on the hydrolytic stability of a fully deprotected xanthosine 2-phosphate diester has revealed that it is more stable at higher pH.

摘要

通过一锅法实现了黄嘌呤核苷的 O-磷酸化，该方法包括使用亚磷酰胺和 N-(氰甲基)二甲铵三氟甲磺酸（CMMT）对适当保护的黄嘌呤核苷衍生物的 2-羰基进行膦酰化，然后对得到的黄嘌呤核苷 2-磷酸三酯进行氧化和脱保护。此外，对完全脱保护的黄嘌呤核苷 2-磷酸二酯的水解稳定性的研究表明，它在较高 pH 值下更稳定。