"Reliable Chemical Synthesis of Oligoribonucleotides (RNA) with 2′-O-[(Triisopropylsilyl)oxy]methyl(2′-O-tom)-Protected Phosphoramidites"

Stefan Pitsch, Patrick A. Weiss, Luzi Jenny, Alfred Stutz, Xiaolin Wu

Published 2001-12-19 in Helvetica Chimica Acta volume Volume 84, Issue 12, pages 377 .

Pubmed ID: -
DOI identifier: 10.1002/1522-2675(20011219)84:12<3773::AID-HLCA377

A method for the introduction of the 2′-O-[(triisopropylsilyl)oxy]methyl (=tom) group into N-acetylated, 5′-O-dimethoxytritylated ribonucleosides is presented. The corresponding 2′-O-tom-protected phosphoramidite building blocks were obtained in pure form and were successfully employed for the routine synthesis of oligoribonucleotides on DNA synthesizers. Under DNA coupling conditions (2.5 min coupling time for a 1.5-μmol synthesis scale) and with 5-(benzylthio)-1H-tetrazole (BTT) as activator, 2′-O-tom-protected phosphoramidites exhibited average coupling yields >99.4%. The combination of N-acetyl and 2′-O-tom protecting groups allowed a reliable and complete two-step deprotection, first with MeNH2 in EtOH/H2O and then with Bu4NF in THF, without concomitant destruction of the product RNA sequences.

Entry added on: 2012-06-27 08:51:40.352005, by a user: mark