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2′-Deoxy-2′-fluoro-arabinonucleic acid: a valid alternative to DNA for biotechnological applications using charge transport

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Abstract

The non-biological 2′-deoxy-2′-fluoro-arabinonucleic acid (2′F-ANA) may be used as a valid alternative to DNA in biomedical and electronic applications because of its higher resistance to hydrolysis and nuclease degradation. However, the advantage of using 2′F-ANA in such applications also depends on its charge-transfer properties compared to DNA. In this study, we compare the charge conduction properties of model 2′F-ANA and DNA double-strands, using structural snapshots from MD simulations to calculate the electronic couplings and reorganization energies associated with the hole transfer steps between adjacent nucleobase pairs. Inserting these charge-transfer parameters into a kinetic model for charge conduction, we find similar conductive properties for DNA and 2′F-ANA. Moreover, we find that 2′F-ANA's enhanced chemical stability does not correspond to a reduction in the nucleobase π-stack structural flexibility relevant to both electronic couplings and reorganization free energies. Our results promote the use of 2′F-ANA in applications that can be based on charge transport, such as biosensing and chip technology, where its chemical stability and conductivity can advantageously combine.

Graphical abstract: 2′-Deoxy-2′-fluoro-arabinonucleic acid: a valid alternative to DNA for biotechnological applications using charge transport

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Publication details

The article was received on 30 Aug 2019, accepted on 05 Oct 2019 and first published on 07 Oct 2019


Article type: Paper
DOI: 10.1039/C9CP04805G
Phys. Chem. Chem. Phys., 2019, Advance Article

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    2′-Deoxy-2′-fluoro-arabinonucleic acid: a valid alternative to DNA for biotechnological applications using charge transport

    R. D. Teo, E. R. Smithwick and A. Migliore, Phys. Chem. Chem. Phys., 2019, Advance Article , DOI: 10.1039/C9CP04805G

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