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Synthesis and biophysical characterization of oligonucleotides containing a 4'-selenonucleotide

Synthesis and biophysical characterization of oligonucleotides containing a 4'-selenonucleotide
Synthesis and biophysical characterization of oligonucleotides containing a 4'-selenonucleotide
The first synthesis of oligonucleotides containing 4'-selenium-modified ribonucleotides (4'-Se-rN) is described. Four sequences containing 4'-Se-rT were successfully synthesized and compared with DNA and RNA oligonucleotides containing a dT, rT, or LNA insert in place of the 4'-Se-rT. The 4'-Se-rT behaved more like rT than dT in its effects on binding affinity, despite the DNA-like structure previously observed for the nucleoside, suggesting that a conformational switch occurs upon incorporation into an oligonucleotide. Incorporation of 4'-Se-rT into A-RNA and hybrid duplexes led to increased binding affinity, while incorporation into B-DNA destabilized the duplex to the same extent as an rT nucleotide.
0002-7863
8578-8579
Watts, Jonathan K.
c4de85ee-aaa3-4e7d-99b3-147a4de4f01c
Johnston, Blair D.
97d24281-a810-4832-9b66-87de354c24a5
Jayakanthan, Kumarasamy
ae75b54f-d913-4be0-aae7-e764438fe296
Wahba, Alexander S.
4e5538c4-7969-4be6-bfa8-11a1364051dc
Pinto, B. Mario
552358f7-e219-4fa5-9211-e05b519066c9
Damha, Masad J.
31a9645e-2a72-4cc5-aa35-b82a16f1d535
Watts, Jonathan K.
c4de85ee-aaa3-4e7d-99b3-147a4de4f01c
Johnston, Blair D.
97d24281-a810-4832-9b66-87de354c24a5
Jayakanthan, Kumarasamy
ae75b54f-d913-4be0-aae7-e764438fe296
Wahba, Alexander S.
4e5538c4-7969-4be6-bfa8-11a1364051dc
Pinto, B. Mario
552358f7-e219-4fa5-9211-e05b519066c9
Damha, Masad J.
31a9645e-2a72-4cc5-aa35-b82a16f1d535

Watts, Jonathan K., Johnston, Blair D., Jayakanthan, Kumarasamy, Wahba, Alexander S., Pinto, B. Mario and Damha, Masad J. (2008) Synthesis and biophysical characterization of oligonucleotides containing a 4'-selenonucleotide. Journal of the American Chemical Society, 130 (27), 8578-8579. (doi:10.1021/ja802205u). (PMID:18543920)

Record type: Article

Abstract

The first synthesis of oligonucleotides containing 4'-selenium-modified ribonucleotides (4'-Se-rN) is described. Four sequences containing 4'-Se-rT were successfully synthesized and compared with DNA and RNA oligonucleotides containing a dT, rT, or LNA insert in place of the 4'-Se-rT. The 4'-Se-rT behaved more like rT than dT in its effects on binding affinity, despite the DNA-like structure previously observed for the nucleoside, suggesting that a conformational switch occurs upon incorporation into an oligonucleotide. Incorporation of 4'-Se-rT into A-RNA and hybrid duplexes led to increased binding affinity, while incorporation into B-DNA destabilized the duplex to the same extent as an rT nucleotide.

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e-pub ahead of print date: 11 June 2008
Published date: 9 July 2008
Organisations: Chemistry

Identifiers

Local EPrints ID: 340224
URI: http://eprints.soton.ac.uk/id/eprint/340224
ISSN: 0002-7863
PURE UUID: e69ed7a2-d848-4678-80aa-1f60e2a77f3c

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Date deposited: 15 Jun 2012 12:52
Last modified: 16 Jul 2019 22:00

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Contributors

Author: Jonathan K. Watts
Author: Blair D. Johnston
Author: Kumarasamy Jayakanthan
Author: Alexander S. Wahba
Author: B. Mario Pinto
Author: Masad J. Damha

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