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Int. J. Mol. Sci. 2015, 16(8), 17798-17811; doi:10.3390/ijms160817798

2,6-Bis(1,4,7,10-tetraazacyclododecan-1-ylmethyl)pyridine and Its Benzene Analog as Nonmetallic Cleaving Agents of RNA Phosphodiester Linkages

Department of Chemistry, University of Turku, Vatselankatu 2, FIN-20014 Turku, Finland
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Academic Editor: Eric C. Long
Received: 13 July 2015 / Revised: 13 July 2015 / Accepted: 28 July 2015 / Published: 3 August 2015
(This article belongs to the Special Issue Low Molecular Weight DNA and RNA Binding Agents)
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Abstract

2,6-Bis(1,4,7,10-tetraazacyclododecan-1-ylmethyl)pyridine (11a) and 1,3-bis(1,4,7,10-tetraazacyclododecan-1-ylmethyl)benzene (11b) have been shown to accelerate at 50 mmol·L−1 concentration both the cleavage and mutual isomerization of uridylyl-3′,5′-uridine and uridylyl-2′,5′-uridine by up to two orders of magnitude. The catalytically active ionic forms are the tri- (in the case of 11b) tetra- and pentacations. The pyridine nitrogen is not critical for efficient catalysis, since the activity of 11b is even slightly higher than that of 11a. On the other hand, protonation of the pyridine nitrogen still makes 11a approximately four times more efficient as a catalyst, but only for the cleavage reaction. Interestingly, the respective reactions of adenylyl-3′,5′-adenosine were not accelerated, suggesting that the catalysis is base moiety selective. View Full-Text
Keywords: NA; phosphodiester; cleavage; isomerization; catalysis; azacrown NA; phosphodiester; cleavage; isomerization; catalysis; azacrown
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Lain, L.; Lahdenpohja, S.; Lönnberg, H.; Lönnberg, T. 2,6-Bis(1,4,7,10-tetraazacyclododecan-1-ylmethyl)pyridine and Its Benzene Analog as Nonmetallic Cleaving Agents of RNA Phosphodiester Linkages. Int. J. Mol. Sci. 2015, 16, 17798-17811.

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