A Bis(guanidinium)alcohol Attached to a Hairpin Polyamide: Synthesis, DNA Binding, and Plasmid Cleavage | Zendy

WirthHamdoune Daniela | Zendy; Ullrich Stefan | Zendy; Scheffer Ute | Zendy; Radanović Toni | Zendy; Dürner Gerd | Zendy; Göbel Michael W. | Zendy

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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.

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