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Factors influencing hairpin oligonucleotide cyclization by the uncatalyzed alkyne-azide cycloaddition (AAC) reaction

Factors influencing hairpin oligonucleotide cyclization by the uncatalyzed alkyne-azide cycloaddition (AAC) reaction
Factors influencing hairpin oligonucleotide cyclization by the uncatalyzed alkyne-azide cycloaddition (AAC) reaction
Cyclization of short hairpin oligonucleotides (ODNs) containing unactivated alkynes and alkyl azides produces triazole-linked products slowly in the absence of CuI catalysis. The factors affecting the rate of this cycloaddition reaction have been investigated on a variety of hairpin sequences. The reaction proceeds best at intermediate concentrations of sodium chloride, but is inhibited by phosphate and Tris buffers. It is accelerated by increasing the temperature provided that Watson–Crick base pairing can occur. The rationale for these observations is discussed.
AAC reaction, alkyne azide, DNA cyclization, hairpin, uncatalyzed
0033-4545
1
El-Sagheer, Afaf H.
05b8295a-64ad-4fdf-ad57-c34934a46c04
Brown, Tom
a64aae36-bb30-42df-88a2-11be394e8c89
El-Sagheer, Afaf H.
05b8295a-64ad-4fdf-ad57-c34934a46c04
Brown, Tom
a64aae36-bb30-42df-88a2-11be394e8c89

El-Sagheer, Afaf H. and Brown, Tom (2010) Factors influencing hairpin oligonucleotide cyclization by the uncatalyzed alkyne-azide cycloaddition (AAC) reaction. Pure and Applied Chemistry, 1. (doi:10.1351/PAC-CON-09-10-42).

Record type: Article

Abstract

Cyclization of short hairpin oligonucleotides (ODNs) containing unactivated alkynes and alkyl azides produces triazole-linked products slowly in the absence of CuI catalysis. The factors affecting the rate of this cycloaddition reaction have been investigated on a variety of hairpin sequences. The reaction proceeds best at intermediate concentrations of sodium chloride, but is inhibited by phosphate and Tris buffers. It is accelerated by increasing the temperature provided that Watson–Crick base pairing can occur. The rationale for these observations is discussed.

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More information

Published date: 13 May 2010
Keywords: AAC reaction, alkyne azide, DNA cyclization, hairpin, uncatalyzed

Identifiers

Local EPrints ID: 153399
URI: http://eprints.soton.ac.uk/id/eprint/153399
ISSN: 0033-4545
PURE UUID: efb8cc9c-3311-4e73-9774-9a5cb59dd924
ORCID for Afaf H. El-Sagheer: ORCID iD orcid.org/0000-0001-8706-1292

Catalogue record

Date deposited: 19 May 2010 15:42
Last modified: 14 Mar 2024 02:51

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Contributors

Author: Afaf H. El-Sagheer ORCID iD
Author: Tom Brown

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