The "Speedy" Synthesis of Atom‐Specific 15N Imino/Amido‐Labeled RNA. Issue 33 (17th June 2015)

• Record Type: Journal Article
• Authors: Neuner, Sandro; Santner, Tobias; Kreutz, Christoph; Micura, Ronald
• Is Part Of: Chemistry. Volume 21:Issue 33(2015)
• Page Start: 11634
• Page End: 11643
• Publication Date: 2015-06-17
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201501275
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Although numerous reports on the synthesis of atom‐specific ¹⁵N‐labeled nucleosides exist, fast and facile access to the corresponding phosphoramidites for RNA solid‐phase synthesis is still lacking. This situation represents a severe bottleneck for NMR spectroscopic investigations on functional RNAs. Here, we present optimized procedures to speed up the synthesis of ¹⁵N(1) adenosine and ¹⁵N(1) guanosine amidites, which are the much needed counterparts of the more straightforward‐to‐achieve ¹⁵N(3) uridine and ¹⁵N(3) cytidine amidites in order to tap full potential of ¹H/¹⁵N/¹⁵N‐COSY experiments for directly monitoring individual Watson–Crick base pairs in RNA. Demonstrated for two preQ₁ riboswitch systems, we exemplify a versatile concept for individual base‐pair labeling in the analysis of conformationally flexible RNAs when competing structures and conformational dynamics are encountered.</p> </abstract>