Issue 10, 2001

A multinuclear NMR study of the restricted rotation in a bi-imidazole nucleoside

Abstract

Ethenoadenosine, a common nucleoside adduct known to be formed by the action of several industrial and environmental genotoxic compounds on adenosine, undergoes ring-opening in aqueous NaOH solution with the consequent loss of one carbon atom (C5). The prototropic equilibrium and protonation of the resultant bi-imidazole nucleoside was studied by 1H, 13C, and 15N NMR spectroscopy and it was found that in the neutral form an intramolecular H-bonding is in effect between N3″ of the outer imidazole ring and the N6 protons of the inner imidazole ring, giving rise to degenerate tautomeric forms. In the protonated form it is the pyridine-type nitrogen (N3″) of the outer imidazole ring where the proton is predominately located and the reduced intramolecular H-bonding results in essentially unrestricted rotation of the imidazole rings with respect to one another.

Graphical abstract: A multinuclear NMR study of the restricted rotation in a bi-imidazole nucleoside [ ]

Supplementary files

Article information

Article type
Paper
Submitted
19 Dec 2000
Accepted
03 Apr 2001
First published
02 May 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 1216-1219

A multinuclear NMR study of the restricted rotation in a bi-imidazole nucleoside

J. Mäki, K. D. Klika, R. Sjöholm and L. Kronberg, J. Chem. Soc., Perkin Trans. 1, 2001, 1216 DOI: 10.1039/B010182F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements