A direct, efficient method for the preparation of siRNAs containing ribo-like North bicyclo[3.1.0]hexane pseudosugars

Montserrat Terrazas; Anna Aviñó; Maqbool A Siddiqui; Victor E Marquez; Ramon Eritja

doi:10.1021/ol200909j

A direct, efficient method for the preparation of siRNAs containing ribo-like North bicyclo[3.1.0]hexane pseudosugars

Org Lett. 2011 Jun 3;13(11):2888-91. doi: 10.1021/ol200909j. Epub 2011 May 9.

Authors

Montserrat Terrazas¹, Anna Aviñó, Maqbool A Siddiqui, Victor E Marquez, Ramon Eritja

Affiliation

¹ Institute for Research in Biomedicine (IRB Barcelona), Networking Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Barcelona, Spain.

PMID: 21553811
DOI: 10.1021/ol200909j

Abstract

An efficient method for the preparation of siRNAs modified with ribo-like North bicyclo[3.1.0]hexane pseudosugars is described. The combined use of 2'-O-(2-cyanoethoxymethyl) (CEM) and 2'-O-TBDMS protection was successfully employed for RNA synthesis with the added advantage that both groups were efficiently removed in a single step. The resulting North ribo-methanocarba-modified siRNAs are compatible with the intracellular RNAi machinery and can mediate specific degradation of target mRNA.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Carbasugars / chemistry*
Molecular Structure
Nucleosides / chemical synthesis*
Nucleosides / chemistry
RNA, Messenger / drug effects
RNA, Small Interfering / chemical synthesis*
RNA, Small Interfering / chemistry
Sequence Homology, Nucleic Acid

Substances

Carbasugars
Nucleosides
RNA, Messenger
RNA, Small Interfering