Adenosine radicals tagged with a fixed-charge group were generated in the gas phase and structurally characterized by tandem mass spectrometry, deuterium labeling, and UV/Vis action spectroscopy. Experimental results in combination with Born–Oppenheimer molecular dynamics, ab initio, and excited-state calculations led to unambiguous assignment of adenosine radicals as N-7 hydrogen atom adducts. The charge-tagged radicals were found to be electronically equivalent to natural DNA nucleoside radicals.

Supporting Information

References

1D. E. Holmes, R. B. Ingalls, L. S. Myers, Jr., Int. J. Radiat. Biol. 1967, 13, 225–234.
CAS PubMed Web of Science® Google Scholar
2P. N. Moorthy, E. Hayon, J. Am. Chem. Soc. 1975, 97, 3345–3350.
10.1021/ja00845a012
CAS PubMed Web of Science® Google Scholar
3A. Hissung, C. von Sonntag, D. Veltwisch, K.-D. Asmus, Int. J. Radiat. Biol. 1981, 39, 63–71.
10.1080/09553008114550081
CAS PubMed Web of Science® Google Scholar
4K. J. Visscher, M. P. De Haas, H. Loman, B. Vojnovic, J. M. Warman, Int. J. Radiat. Biol. 1987, 52, 745–753.
10.1080/09553008714552251
CAS PubMed Web of Science® Google Scholar
5M. D. Sevilla, R. Failor, C. Clark, R. A. Holroud, M. Pettei, J. Phys. Chem. 1976, 80, 353–358.
10.1021/j100545a003
CAS Web of Science® Google Scholar
6L. P. Candeias, S. Steenken, J. Phys. Chem. 1992, 96, 937–944.
10.1021/j100181a074
CAS Web of Science® Google Scholar
7J. Barnes, W. A. Bernhard, J. Phys. Chem. 1993, 97, 3401–3408.
10.1021/j100115a053
CAS Web of Science® Google Scholar
8J. Barnes, W. A. Bernhard, J. Phys. Chem. 1994, 98, 10969–10977.
10.1021/j100093a045
CAS Web of Science® Google Scholar
9X. Chen, E. A. Syrstad, M. T. Nguyen, P. Gerbaux, F. Tureček, J. Phys. Chem. A 2005, 109, 8121–8132.
10.1021/jp0529725
CAS PubMed Web of Science® Google Scholar
10C. Yao, M. Cuadrado-Peinado, M. Polášek, F. Tureček, Angew. Chem. Int. Ed. 2005, 44, 6708–6711;
10.1002/anie.200502363
CAS PubMed Web of Science® Google Scholar
Angew. Chem. 2005, 117, 6866–6869.
10.1002/ange.200502363
Web of Science® Google Scholar
11J. A. Korn, J. Urban, A. Dang, H. T. H. Nguyen, F. Turecek, J. Phys. Chem. Lett. 2017, 8, 4100–4107.
10.1021/acs.jpclett.7b01856
CAS PubMed Web of Science® Google Scholar
12“Laser Photodissociation and Spectroscopy of Mass-Separated Biomolecular Ions”: R. Antoine, P. Dugourd, in Lecture Notes in Chemistry, Vol. 83 (Eds.: ), Springer, Heidelberg, 2013, pp. 93–116.
Google Scholar
13J. E. P. Syka, J. J. Coon, M. J. Schroeder, J. Shabanowitz, D. F. Hunt, Proc. Natl. Acad. Sci. USA 2004, 101, 9528–9533.
10.1073/pnas.0402700101
CAS PubMed Web of Science® Google Scholar
14S. A. Shaffer, F. Tureček, J. Am. Chem. Soc. 1994, 116, 8647–8653.
10.1021/ja00098a026
CAS Web of Science® Google Scholar
15D. E. Goeringer, S. A. McLuckey, J. Chem. Phys. 1996, 104, 2214–2221.
10.1063/1.471812
CAS Web of Science® Google Scholar
16S. Gronert, J. Am. Soc. Mass Spectrom. 1998, 9, 845–848.
10.1016/S1044-0305(98)00055-5
CAS Web of Science® Google Scholar
17E. R. Lovejoy, R. R. Wilson, J. Phys. Chem. A 1998, 102, 2309–2315.
10.1021/jp973391l
CAS Web of Science® Google Scholar
18W. A. Donald, G. N. Khairallah, R. A. J. O'Hair, J. Am. Soc. Mass Spectrom. 2013, 24, 811–815.
10.1007/s13361-013-0625-x
CAS PubMed Web of Science® Google Scholar
19A. Dang, Y. Liu, F. Tureček, J. Phys. Chem. A 2019, 123, 3272–3284.
10.1021/acs.jpca.9b01542
CAS PubMed Web of Science® Google Scholar
20J. Reynisson, S. Steenken, Phys. Chem. Chem. Phys. 2005, 7, 659–665.
10.1039/b417343k
CAS PubMed Web of Science® Google Scholar
21S. D. Wetmore, R. J. Boyd, L. A. Eriksson, J. Phys. Chem. B 1998, 102, 10602–10614.
10.1021/jp982417l
CAS Web of Science® Google Scholar

Volume132, Issue20

May 11, 2020

Pages 7846-7851

This is the

German version

of Angewandte Chemie.

Note for articles published since 1962:

Do not cite this version alone.

Take me to the International Edition version with citable page numbers, DOI, and citation export.

We apologize for the inconvenience.

Charge-Tagged DNA Radicals in the Gas Phase Characterized by UV/Vis Photodissociation Action Spectroscopy

Abstract

Supporting Information

References

References

Information

About Wiley Online Library

Help & Support

Opportunities

Connect with Wiley

Charge-Tagged DNA Radicals in the Gas Phase Characterized by UV/Vis Photodissociation Action Spectroscopy

Abstract

Supporting Information

References

References

Related

Information