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), p. 1904. (doi:10.1039/B900443B). (PMID:19590787).


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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
Digital Object Identifier (DOI): doi:10.1039/B900443B
ISSNs: 1477-0520 (print)
Organisations: Chemistry, Organic Chemistry: SCF
ePrint ID: 342429
Date :
Date Event
19 March 2009e-pub ahead of print
Date Deposited: 29 Aug 2012 11:39
Last Modified: 17 Apr 2017 16:40
Further Information:Google Scholar

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