Chimeric RNA with modified backbones: alternating methylene(methylimino) linked phosphodiester backbone oligonucleotides with 2'-OH and 2'-OMe groups

M Prhavc; B Bhat; G Just; P D Cook; M Manoharan

doi:10.1081/NCN-100002476

Chimeric RNA with modified backbones: alternating methylene(methylimino) linked phosphodiester backbone oligonucleotides with 2'-OH and 2'-OMe groups

Nucleosides Nucleotides Nucleic Acids. 2001 Apr-Jul;20(4-7):995-7. doi: 10.1081/NCN-100002476.

Authors

M Prhavc¹, B Bhat, G Just, P D Cook, M Manoharan

Affiliation

¹ Department of Medicinal Chemistry, Isis Pharmaceuticals, Inc., Carlsbad, California, USA.

PMID: 11563162
DOI: 10.1081/NCN-100002476

Abstract

Synthesis of a novel ribo-MMI dimer with 2'-OH and 2'-OMe in 5'- and 3'-nucleosides, respectively is presented. The synthesis was accomplished by reductive coupling of 3'-deoxy-3'-C-formyluridine and 2'-O-methyl-5'-O-methylaminouridine via a thioacetal as the key intermediate for the top part of the dimer. Incorporation of ribo-MMI dimers into oligonucleotides increased binding affinity for target RNA.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Oligonucleotides / chemical synthesis
Oligonucleotides / chemistry*
Organophosphates / chemistry*
RNA / chemical synthesis
RNA / chemistry*

Substances

Oligonucleotides
Organophosphates
RNA