The 9-fluorenylmethoxycarbonyl (Fmoc) group and its use in oligonucleotide synthesis.

H Schirmeister-Tichy, G G Alvarado, W Pfleiderer
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引用次数: 3

Abstract

The introduction of the base-labile 9-fluorenylmethoxycarbonyl (Fmoc) group into the exocyclic amino function of 2'-deoxynucleosides and their dimethoxytritylation and phosphitylation is described. The resulting key intermediates were investigated in the built-up of different oligodeoxyribonucleoside phosphate and thiophosphate chains which were deprotected under mild basic conditions leading to crude oligomers of high purity.

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9-芴基甲氧羰基(Fmoc)基团及其在寡核苷酸合成中的应用。
描述了在2'-脱氧核苷的外环氨基官能团中引入碱基不稳定的9-芴基甲氧羰基(Fmoc)基团及其二甲氧基三甲基化和磷酸化。研究了不同的低聚脱氧核糖核苷磷酸和硫代磷酸链在温和的碱性条件下脱保护,得到高纯度的粗低聚物。
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Synthesis and antiviral studies of unsaturated analogues of isomeric dideoxynucleosides. Synthesis, cytotoxic effect and antiviral activity of 1-(beta-D-arabinofuranosyl)-5-bromo-N4-substituted cytosine and 1-(beta-D-arabinofuranosyl)-5-bromo-4-methoxypyrimidin-2(1H)-one derivatives. Intramolecular glycosylation to form 4-methoxy-2,6-dioxopyrimidine nucleosides via O6,5'-cyclonucleosides. Synthesis and biological evaluation of 9-(beta-L-arabinofuranosyl)adenine. Inhibitory potency of 5-benzyluracil, 5-phenylcytosine and 5-phenylpyrimidin-2-one nucleosides against uridine phosphorylase from mouse leukemic L1210 cells.
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