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

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  • 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.
  • 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. (en)
Title
  • Furan-Oxidation-Triggered Inducible DNA Cross-Linking: Acyclic Versus Cyclic Furan-Containing Building Blocks-On the Benefit of Restoring the Cyclic Sugar Backbone
  • Furan-Oxidation-Triggered Inducible DNA Cross-Linking: Acyclic Versus Cyclic Furan-Containing Building Blocks-On the Benefit of Restoring the Cyclic Sugar Backbone (en)
skos:prefLabel
  • Furan-Oxidation-Triggered Inducible DNA Cross-Linking: Acyclic Versus Cyclic Furan-Containing Building Blocks-On the Benefit of Restoring the Cyclic Sugar Backbone
  • Furan-Oxidation-Triggered Inducible DNA Cross-Linking: Acyclic Versus Cyclic Furan-Containing Building Blocks-On the Benefit of Restoring the Cyclic Sugar Backbone (en)
skos:notation
  • RIV/61388963:_____/11:00361001!RIV12-AV0-61388963
http://linked.open...avai/riv/aktivita
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  • P(IAA400550902), P(LC512), Z(AV0Z40550506)
http://linked.open...iv/cisloPeriodika
  • 25
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http://linked.open...aciTvurceVysledku
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  • 200655
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  • RIV/61388963:_____/11:00361001
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  • bioorganic chemistry; DNA; molecular modeling; nucleosides; oxidation (en)
http://linked.open.../riv/klicoveSlovo
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  • DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV
  • [3EA671E05202]
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  • Chemistry - A European Journal
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  • 17
http://linked.open...iv/tvurceVysledku
  • Hocek, Michal
  • Catak, S.
  • Claeys, D. D.
  • Figaroli, S.
  • Madder, A.
  • Schürch, S.
  • Speybroeck, V. V.
  • Stevens, K.
  • Tromp, J. M.
http://linked.open...ain/vavai/riv/wos
  • 000292206600011
http://linked.open...n/vavai/riv/zamer
issn
  • 0947-6539
number of pages
http://bibframe.org/vocab/doi
  • 10.1002/chem.201100067
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