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HERO ID
7637441
Reference Type
Journal Article
Title
Enhanced H-bonding and pi-stacking in DNA: a potent duplex-stabilizing and mismatch sensing nucleobase analogue
Author(s)
Lou, C; Dallmann, A; Marafini, P; Gao, R; Brown, Tom; ,
Year
2014
Journal
Chemical Science
ISSN:
2041-6520
EISSN:
2041-6539
Publisher
ROYAL SOC CHEMISTRY
Location
CAMBRIDGE
Volume
5
Issue
10
Page Numbers
3836-3844
Language
English
DOI
10.1039/c4sc00948g
Web of Science Id
WOS:000341195100019
URL
http://xlink.rsc.org/?DOI=C4SC00948G
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Abstract
X-pyrene is a new nucleic acid duplex stabilizing cytosine analogue that combines enhanced pi-stacking, hydrogen bonding and electrostatic interactions to greatly increase the stability of bulged DNA duplexes and DNA/RNA hybrids. X-pyrene is highly selective for guanine as a partner and duplex stability is reduced dramatically when X-pyrene or a neighboring base is mismatched. An NMR study indicates that the pyrene moiety stacks within the helix, and large changes in fluorescence emission on duplex formation are consistent with this. These favorable properties make X-pyrene a promising cytosine analogue for use in a variety of biological applications.
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