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A Bis(guanidinium)alcohol Attached to a Hairpin Polyamide: Synthesis, DNA Binding, and Plasmid Cleavage
Author(s) -
WirthHamdoune Daniela,
Ullrich Stefan,
Scheffer Ute,
Radanović Toni,
Dürner Gerd,
Göbel Michael W.
Publication year - 2016
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201500566
Subject(s) - phosphodiester bond , polyamide , conjugate , dna , chemistry , plasmid , intramolecular force , titration , cleavage (geology) , stereochemistry , polymer chemistry , combinatorial chemistry , biochemistry , organic chemistry , materials science , rna , composite material , gene , mathematical analysis , mathematics , fracture (geology)
Bis(guanidinium)alcohols have been designed to react with phosphodiester substrates in a fast transphosphorylation step, a quasi‐intramolecular process taking place in contact ion pairs. Here the attachment of such compounds to Dervan‐type hairpin polyamides is described. The resulting conjugate 1 binds to AT‐rich DNA duplexes with affinity similar to that of the parent polyamide as shown by UV melting experiments and CD titrations. Conjugate 1 nicks plasmid DNA at concentrations ranging from micromolar to high nanomolar.