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Disassembly of Chromophore‐Guided DNA Duplexes through Site‐Selective Binding of Coralyne to Pyrene‐Modified Adenine Bases
Author(s) -
Kim Ki Tae,
Choi Tae Su,
Kim Ka Young,
Kim Hugh I.,
Kim Byeang Hyean
Publication year - 2016
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201600230
Subject(s) - stacking , intercalation (chemistry) , chromophore , pyrene , chemistry , dna , dissociation (chemistry) , stereochemistry , duplex (building) , base pair , combinatorial chemistry , photochemistry , organic chemistry , biochemistry
Under ambient conditions the disassembly of self‐duplexes of Py A‐modified oligodeoxyadenylates (i.e., chromophore‐guided DNA assemblies) through intercalative binding of coralyne units to pyrene‐modified adenine ( Py A) bases was carried out. The coralyne units, intercalated site‐selectively on the 3′ sides of the Py A units, are stabilized through π–π stacking interactions. This competitive intercalation destabilizes the stacking interactions of pairs of Py A units, resulting in dissociation of the self‐duplexes. This behavior, which is opposite to that of coralyne‐induced self‐duplex formation of natural oligodeoxyadenylates, was exploited to prepare new types of DNA modules that can be switched between two different duplex states.