Synthesis of Geranyl-2-Thiouridine-Modified RNA

Rui Wang; Phensinee Haruehanroengra; Jia Sheng

doi:10.1002/cpnc.22

Synthesis of Geranyl-2-Thiouridine-Modified RNA

Curr Protoc Nucleic Acid Chem. 2017 Mar 2:68:4.72.1-4.72.13. doi: 10.1002/cpnc.22.

Authors

Rui Wang¹, Phensinee Haruehanroengra¹, Jia Sheng¹

Affiliation

¹ Department of Chemistry and The RNA Institute, University at Albany, State University of New York, Albany, New York.

PMID: 28252182
DOI: 10.1002/cpnc.22

Abstract

This unit describes the chemical synthesis of the S-geranyl-2-thiouridine (ges² U) phosphoramidite and its incorporation into RNA oligonucleotides through solid-phase synthesis. Starting from the 2-thiouracil nucleobase and the protected ribose, the 2-thiouridine is synthesized and the geranyl functionality is introduced into the 2-thio position by using geranyl bromide as the geranylating reagent before the conversion of this modified nucleoside into a phosphoramidite building block. The modified phosphoramidite is used to make the geranyl-RNA oligonucleotides with a solid-phase DNA synthesizer. These RNA strands are then purified by ion-exchange HPLC before further structural and functional studies, such as base pairing and enzyme recognition, can be done. © 2017 by John Wiley & Sons, Inc.

Keywords: geranylation; natural RNA modification; nucleic acids; tRNA.

Publication types

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

MeSH terms

Chemistry Techniques, Synthetic*
RNA / chemical synthesis
RNA / chemistry*
RNA / isolation & purification
Thiouridine / chemistry

Substances

Thiouridine
RNA