Issue 32, 2012
From the journal:

Organic & Biomolecular Chemistry

Click fleximers: a modular approach to purine base-expanded ribonucleoside analogues†

André H. St. Amant,a   Leslie A. Bean,a   J. Peter Guthriea  and  Robert H. E. Hudson*a  

* Corresponding authors

a Department of Chemistry, The University of Western Ontario, London, Ontario, Canada N6A 5B7
E-mail: robert.hudson@uwo.ca
Fax: +01 519 661 3022
Tel: +01 519 661 2166

Abstract

The synthesis of nucleoside analogues incorporating 4-(5-pyrimidinyl)-1,2,3-triazole aglycons as expanded purine nucleobase mimics were accessed using the copper-catalyzed azide–alkyne Huisgen cycloaddition between a ribosyl azide and 5-alkynylpyrimidines. Depending on the nature of the alkyne employed, other nucleoside analogues that possess fluorescence or potential metal-binding properties were prepared. Computational studies were undertaken on the purine analogues and indicate that the heterocycles of the unfused nucleobase prefer a coplanar arrangement and the anti-glycosidic conformer is favoured in most instances.

Graphical abstract: Click fleximers: a modular approach to purine base-expanded ribonucleoside analogues

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Article information

DOI
https://doi.org/10.1039/C2OB25678A
Article type
Paper
Submitted
05 Apr 2012
Accepted
06 Jun 2012
First published
13 Jun 2012

Org. Biomol. Chem., 2012,10, 6521-6525

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Click fleximers: a modular approach to purine base-expanded ribonucleoside analogues

A. H. St. Amant, L. A. Bean, J. P. Guthrie and R. H. E. Hudson, Org. Biomol. Chem., 2012, 10, 6521 DOI: 10.1039/C2OB25678A

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