Nucleoside and nucleotide analogues by catalyst free Huisgen nitrile oxide–alkyne 1,3-dipolar cycloaddition

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Algay, Virginie, Singh, Ishwar and Heaney, Frances (2010) Nucleoside and nucleotide analogues by catalyst free Huisgen nitrile oxide–alkyne 1,3-dipolar cycloaddition. Organic & Biomolecular Chemistry, 8. pp. 391-397. ISSN 1477-0520

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Abstract

An efficient, catalyst free, 1,3-dipolar cycloaddition strategy to conjugate nucleosides and nucleotides with isoxazoles under atmospheric conditions and in an aqueous environment is reported. The protocol involves chloramine-T as a practical reagent to induce in situ nitrile oxide formation and the alkyne partner is attached to the sugar residue or the nucleobase. The reactions are regiospecific, fast and high yielding.

Item Type:	Article
Keywords:	Nucleoside; nucleotide analogues; catalyst free Huisgen nitrile oxide–alkyne 1,3-dipolar cycloaddition;
Academic Unit:	Faculty of Science and Engineering > Chemistry
Item ID:	4295
Depositing User:	Dr. Frances Heaney
Date Deposited:	09 Apr 2013 13:18
Journal or Publication Title:	Organic & Biomolecular Chemistry
Publisher:	Royal Society of Chemistry
Refereed:	Yes
Related URLs:	Publisher
URI:	https://mu.eprints-hosting.org/id/eprint/4295
Use Licence:	This item is available under a Creative Commons Attribution Non Commercial Share Alike Licence (CC BY-NC-SA). Details of this licence are available here

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Nucleoside and nucleotide analogues by catalyst free Huisgen nitrile oxide–alkyne 1,3-dipolar cycloaddition

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