A1 Journal article – refereed

Synthesis of Short Oligodeoxyribonucleotides by Phosphotriester Chemistry on a Precipitative Tetrapodal Support




List of Authors: Vyacheslav Kungurtsev, Pasi Virta, Harri Lönnberg

Publisher: WILEY-V C H VERLAG GMBH

Publication year: 2013

Journal: European Journal of Organic Chemistry

Journal name in source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Journal acronym: EUR J ORG CHEM

Volume number: 35

Issue number: 35

Number of pages: 5

ISSN: 1434-193X

DOI: http://dx.doi.org/10.1002/ejoc.201301352


Abstract

Short oligodeoxyribonucleotides have been assembled from appropriately protected nucleoside 3-(benzotriazol-1-yl 2-chlorophenyl phosphate) derivatives on hundred-milligram scales on a soluble tetrakis-O-(4-azidomethylphenyl)pentaerythritol support bearing four 3-O-(4-pentynoyl)thymidines. Small-molecule reagents and waste were removed by two precipitations of the support-bound growing oligonucleotides with methanol, the first after removal of the 5-protecting group and the second after coupling. The building blocks were obtained by one-step phosphorylation of commercially available protected nucleosides with bis(benzotriazol-1-yl) 2-chlorophenyl phosphate. Removal of the phosphate protecting groups from the completed chain with (E)-2-nitrobenzaldoxime followed by conventional ammonolysis allowed precipitation of the oligonucleotide as the sodium salt with ethanol.



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