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Issue 3, 2017
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Enzymatic incorporation and utilization of an emissive 6-azauridine

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Abstract

To display favorable fluorescent properties, the non-emissive native nucleosides need to be modified. Here we present a motif that relies on conjugating 5-membered aromatic heterocycles (e.g., thiophene) to a 6-azapyrimidine (1,2,4-triazine) core. Synthetic accessibility and desirable photophysical properties make these nucleosides attractive candidates for enzymatic incorporation and biochemical assays. While 6-azauridine triphosphate is known to be poorly tolerated by polymerases in RNA synthesis, we illustrate that conjugating a thiophene ring at position 5 overcomes such limitations, facilitating its T7 RNA polymerase-mediated in vitro transcription incorporation into RNA constructs. We further show that the modified transcripts can be ligated to longer oligonucleotides to form singly modified RNAs, as illustrated for an A-site hairpin model RNA construct, which was employed to visualize aminoglycoside antibiotics binding.

Graphical abstract: Enzymatic incorporation and utilization of an emissive 6-azauridine

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Supplementary files

Article information


Submitted
22 Sep 2016
Accepted
12 Dec 2016
First published
12 Dec 2016

This article is Open Access

Org. Biomol. Chem., 2017,15, 684-690
Article type
Paper

Enzymatic incorporation and utilization of an emissive 6-azauridine

P. A. Hopkins, L. S. McCoy and Y. Tor, Org. Biomol. Chem., 2017, 15, 684
DOI: 10.1039/C6OB02080A

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