The Components of xRNA: Synthesis and Fluorescence of a Full Genetic Set of Size-Expanded Ribonucleosides

Armando R. Hernández and Eric T. Kool*

Department of Chemistry, Stanford University, Stanford, California 94305-5080, United States

Org. Lett., 2011, 13 (4), pp 676–679

DOI: 10.1021/ol102915f

Publication Date (Web): January 7, 2011

Copyright © 2011 American Chemical Society

kool@stanford.edu

Cite this:Org. Lett. 13, 4, 676-679

Abstract

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The synthesis and properties of a full set of four benzo-expanded ribonucleosides (xRNA), analogous to A, G, C, and U RNA monomers, are described. The nucleosides are efficient fluorophores with emission maxima of 369−411 nm. The compounds are expected to be useful as RNA pathway probes and as components of an unnatural ribopolymer.

Experimental procedures, NMR data, fluorescence experiment details, UV−vis and fluorescence spectra, and fluorescence lifetime data. This material is available free of charge via the Internet at http://pubs.acs.org.

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The Components of xRNA: Synthesis and Fluorescence of a Full Genetic Set of Size-Expanded Ribonucleosides

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