Furan-Oxidation-Triggered Inducible DNA Cross-Linking: Acyclic Versus Cyclic Furan-Containing Building Blocks-On the Benefit of Restoring the Cyclic Sugar Backbone

0361001 - ÚOCHB 2012 RIV DE eng J - Journal Article
Stevens, K. - Claeys, D. D. - Catak, S. - Figaroli, S. - Hocek, Michal - Tromp, J. M. - Schürch, S. - Speybroeck, V. V. - Madder, A.
Furan-Oxidation-Triggered Inducible DNA Cross-Linking: Acyclic Versus Cyclic Furan-Containing Building Blocks-On the Benefit of Restoring the Cyclic Sugar Backbone.
Chemistry - A European Journal. Roč. 17, č. 25 (2011), s. 6940-6953. ISSN 0947-6539. E-ISSN 1521-3765
R&D Projects: GA MŠMT LC512; GA AV ČR IAA400550902
Institutional research plan: CEZ:AV0Z40550506
Keywords : bioorganic chemistry * DNA * molecular modeling * nucleosides * oxidation
Subject RIV: CC - Organic Chemistry
Impact factor: 5.925, year: 2011

We recently introduced a furan-oxidation-based methodology for crosslinking of nucleic acids. Given the destabilization of duplexes observed upon introduction of the initially designed furan-modified building block into DNA duplexes, we explore here the potential benefits of two new building blocks featuring an extended aromatic system and a restored cyclic backbone. Thorough experimental analysis of crosslinking reactions in a series of contexts, combined with theoretical calculations, permit structural characterization of the formed species and allow assessment of the origin of the enhanced cross-link selectivity. Our experiments clearly show that the modular nature of the furan-modified building blocks used in the current cross-linking strategy allow for fine tuning of both yield and selectivity of the interstrand crosslinking reaction.
Permanent Link: http://hdl.handle.net/11104/0198423