Studies on the hydrolytic stability of 2′-fluoroarabinonucleic acid (2′F-ANA)
Watts, Jonathan K., Katolik, Adam, Viladoms, Júlia and Damha, Masad J. (2009) Studies on the hydrolytic stability of 2′-fluoroarabinonucleic acid (2′F-ANA). Organic & Biomolecular Chemistry, 7, (9), 1904. (doi:10.1039/B900443B). (PMID:19590787).
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Description/Abstract
The stability of 2'-deoxy-2'-fluoroarabinonucleic acid (2'F-ANA) to hydrolysis under acidic and basic conditions was compared to that of DNA, RNA and 2'F-RNA. In enzyme-free simulated gastric fluid (pH approximately 1.2), 2'F-ANA was found to have dramatically increased stability (virtually no cleavage observed after 2 days) with respect to both DNA (t(1/2) approximately 2 min) and RNA (t(1/2) approximately 3 h (PO) or 3 days (PS)). These results were observed for both phosphodiester and phosphorothioate backbones and with multiple mixed-base sequences. Under basic conditions, 2'F-ANA also showed good stability. In 1 M NaOH at 65 degrees C, 2'F-ANA had a t(1/2) of approximately 20 h, while RNA was entirely degraded in a few minutes. Furthermore, the nuclease cleavage of phosphorothioate 2'F-ANA and DNA by snake venom phosphodiesterase was studied in detail. One diastereomer of the PS-2'F-ANA linkage was found to be much more vulnerable to enzymatic cleavage than the other, which is parallel to the properties observed for PS-DNA. Additional studies of 2'F-ANA-containing oligonucleotides are warranted based on the excellent stability properties described here
| Item Type: | Article |
|---|---|
| ISSNs: | 1477-0520 (print) 1477-0539 (electronic) |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Faculty of Natural and Environmental Sciences > Chemistry Faculty of Natural and Environmental Sciences > Chemistry > Chemical Biology Group Faculty of Natural and Environmental Sciences > Chemistry > Molecular Diagnostics & Therapeutics |
| Item ID: | 342429 |
| Date Deposited: | 29 Aug 2012 11:39 |
| Last Modified: | 29 Aug 2012 11:39 |
| Contributors: | Watts, Jonathan K. (Author) Katolik, Adam (Author) Viladoms, Júlia (Author) Damha, Masad J. (Author) |
| Date: | 19 March 2009 |
| Status: | Unpublished |
| URI: | http://eprints.soton.ac.uk/id/eprint/342429 |
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