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Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Assembly of Short Oligoribonucleotides from Commercially Available Building Blocks on a Tetrapodal Soluble Support

Author(s): Alejandro Gimenez Molina, Amit M. Jabgunde, Pasi Virta and Harri Lonnberg

Volume 12 , Issue 2 , 2015

Page: [202 - 207] Pages: 6

DOI: 10.2174/1570179411666141120215703

Price: $65

Abstract

A workable method for the preparation of short oligoribonucleotides from commercially available 5´-O-(4,4´- dimethoxytrityl)-2´-O-(tert-butyldimethylsilyl)ribonucleoside 3´-(2-cyanoethyl-N,N-diisopropylphosphoramidite) building blocks on a soluble tetrakis-O-[4-(1,2,3-triazol-1-yl)methylphenyl]pentaerythritol support has been developed. The 3´-terminal nucleoside was attached as a 3´-O-(4-pentynoyl) derivative to the support by Cu(I) catalyzed click reaction. The coupling cycle consisted of 4,5-dicyanoimidazole promoted coupling in MeCN with 1.5 equiv. of the monomeric building block, conventional iodine oxidation and precipitation from water followed by flash chromatographic purification. Treatment with triethylamine, followed by ammonolysis and desilylation with Et3N(HF)3 afforded the oligoribonucleotide. As a proof of concept, a pentamer 3´-UUGCA-5´ was prepared in 46% overall yield.

Keywords: Nucleosides, nucleotides, oligoribonucleotides, phosphoramidites, synthesis, soluble support.

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