Solution-Phase Synthesis of Short Oligo-2'-deoxyribonucleotides by Using Clustered Nucleosides as a Soluble Support

: Vyacheslav Kungurtsev, Jouni Laakkonen, Alejandro Gimenez Molina, Pasi Virta

Publisher: WILEY-V C H VERLAG GMBH

: 2013

: European Journal of Organic Chemistry

: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

: EUR J ORG CHEM

: 29

: 2013

: 29

: 6687

: 6693

: 7

: 1434-193X

DOI: https://doi.org/10.1002/ejoc.201300864

5-O-(4,4-Dimethoxytrityl)thymidine was attached to a pentaerythrityl-derived core, and the resulting tetravalent nucleoside cluster and the next dendritic generations served as a soluble support for the synthesis of short oligo-2-deoxyribonucleotides in solution. Couplings using a small excess (1.5 equiv. per 5-OH group) of the standard phosphoramidite building blocks proved efficient, and the products could be purified by quantitative precipitation from methanol. Ammonolysis released nearly homogeneous oligonucleotides (CCT, GCT, ACT, and AGCCT) in high yields.