Synthesis and properties of fluorescent cycloSal nucleotides based on the pyrimidine nucleoside m5K and its 2′,3′-dideoxy analog dM5K

被引：6

作者：

Jessen, HJ ^{[1
]}

Fendrich, W ^{[1
]}

Meier, C ^{[1
]}

机构：

[1] Univ Hamburg, Inst Organ Chem, D-20146 Hamburg, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 2006卷 / 04期

关键词：

pronucleotides; cycloSal triesters; fluorescence; nucleosides; antiviral agents;

D O I：

10.1002/ejoc.200500532

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the fluorescent thymidine nucleoside analog 5-methyl-pyrimidin-2-one nucleoside 1 (m(5)K) and that of its 2',3'-dideoxy derivative 2 (dm(5)K) are described. Moreover, the conversion of 1 and 2 into the corresponding 3-methyl-cycloSal-phosphate triesters 11 and 12 or an enzyme-cleavable prodrug 5-acetoxymethylpropionate-cycloSal-phosphate triester 13, and the fluorescence and hydrolysis proper-ties of these new lipophilic triesters are reported. Finally, the suitability of these cycloSal pronucleotides as probes is demonstrated in a cell-extract hydrolysis experiment and a model study for cell uptake. (c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006.

引用

页码：924 / 931

页数：8

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