Syntheses of (15)N-labeled pre-queuosine nucleobase derivatives

Jasmin Levic; Ronald Micura

doi:10.3762/bjoc.10.199

Syntheses of (15)N-labeled pre-queuosine nucleobase derivatives

Beilstein J Org Chem. 2014 Aug 18:10:1914-8. doi: 10.3762/bjoc.10.199. eCollection 2014.

Authors

Jasmin Levic¹, Ronald Micura¹

Affiliation

¹ Institute of Organic Chemistry, University of Innsbruck and Center for Molecular Biosciences Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria.

Abstract

Pre-queuosine or queuine (preQ1) is a guanine derivative that is involved in the biosynthetic pathway of the hypermodified tRNA nucleoside queuosine (Que). The core structure of preQ1 is represented by 7-(aminomethyl)-7-deazaguanine (preQ1 base). Here, we report the synthesis of three preQ1 base derivatives with complementary (15)N-labeling patterns, utilizing [(15)N]-KCN, [(15)N]-phthalimide, and [(15)N3]-guanidine as cost-affordable (15)N sources. Such derivatives are required to explore the binding process of the preQ1 base to RNA targets using advanced NMR spectroscopic methods. PreQ1 base specifically binds to bacterial mRNA domains and thereby regulates genes that are required for queuosine biosynthesis.

Keywords: heterocycles; ligands; nucleic acids; nucleobases; nucleosides; pyrrolopyrimidinones.