title: Synthesis of Geranyl-2-Thiouridine-Modified RNA.
abstract: This unit describes the chemical synthesis of the S-geranyl-2-thiouridine (ges2U) 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.
authors.affiliation: Department of Chemistry and The RNA Institute, University at Albany, State University of New York, Albany, New York.
authors.forename: Rui
authors.initials: R
authors.lastname: Wang
authors.affiliation: Department of Chemistry and The RNA Institute, University at Albany, State University of New York, Albany, New York.
authors.forename: Phensinee
authors.initials: P
authors.lastname: Haruehanroengra
authors.affiliation: Department of Chemistry and The RNA Institute, University at Albany, State University of New York, Albany, New York.
authors.forename: Jia
authors.initials: J
authors.lastname: Sheng
mesh_terms: D060326:Chemistry Techniques, Synthetic; D012313:RNA / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D013891:Thiouridine / Q000737:chemistry
chemical_list: D013891:Thiouridine; D012313:RNA
keywords: geranylation; natural RNA modification; nucleic acids; tRNA