Abstract
Reactive oxygen species (ROS) may generate different nucleoside/nucleotide radicals in a cell environment. In this study, the possibility of cyclic-2’-deoxyadenosines formation by a rearrangement of their free radicals was investigated. It seems that for cyclic-nucleosides formation, adoption of an O4’-exo conformation by the sugar moiety is necessary. However, this is the energetically unfavoured form of the 2-deoxyribose ring. Moreover, the creation of a O5’, C8 bond in purine deoxy-nucleosides/nucleotides leads to the termination of the DNA elongation process.
Similar content being viewed by others
References
W. Saenger, “Principles of Nucleic Acid Structure”, Springer-Verlag New York Inc. (1984)
J. Cadet, T. Duoki, D. Gasparutto, J-L. Ravanat, Mutat. Res., 531, 5 (2003)
A. Sancar, A.L. Lindsey-Boltz, K. Unsal-Kacmaz, S. Linn, Annu. Rev. Biochem., 73, 39 (2004)
J.P. Brooks, S.D. Wise, A.D. Berry, V.J. Kosmoski, J.M. Smerdon, L.R. Somers, H. Mackie, Y.A. Spoonde, J.E. Acerman, K. Coleman, E.R. Tarone, H.J. Robbins, J. Biol. Chem., 275, 22355 (2000)
I. Kuraoka, P. Robins, Ch. Masutani, F. Hanaoka, D. Gasparutto, J. Cadet, D.R. Wood, Lindhal T., J. Biol. Chem., 52, 49283 (2001).; a) Hogenkamp H.P.C., J. Biol. Chem., 238, 477 (1963); b) K. Keck, Z. Naturforsch., 23B, 1034 (1968); c) Ch. Chatgilialoglu, M. Guerra, Q.G. Mulazzani, J. Am. Chem. Soc., 125, 3839 (2003)
Gaussian 03, Revision D.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R., Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, Gaussian, Inc., Pittsburgh PA (2003)
Ch. Chatgilialoglu, M. Guerra, Q.G. Mulazzani, J. Biol. Chem., 125, 3839 (2003)
A. Romieu, D. Gasparutto, D. Molko, J. Cadet, J. Org. Chem., 63, 5245 (1998)
M. Dizdaroglu, P. Jurga, H. Rodrigez, Free Radic. Biol. Med., 30, 774 (2001)
K. Miaskiewicz, H.J. Miller, F.A. Furcirelli, Nucleic Acid Res., 23, 515 (1995)
F.A. Evangelista, H.F. Schaefer III, J. Phys. Chem., A, 108, 10258 (2004)
S. Sugio, H. Mizuno, K. Kitamura, M. Ikehara, K-I. Tomita, Acta Cryst., Sec. C, 40, 712 (1984)
E.J. Klipartic, K.S. Pitzer, R. Spitzer, J. Am. Chem. Soc., 69, 2483 (1947)
K.A. Brameld, W.A. Goddard III, J. Am. Chem. Soc., 121, 985, 1999
C. Altona, M. Sundaralingam, J. Am. Chem. Soc., 95, 2333 (1973)
K.W. Olson, S. Sussaman, J. Am. Chem. Soc., 104, 270 (1982)
C.S. Harvey, M. Prabhakaran, J. Am. Chem. Soc., 108, 6128 (1986)
D.B. Davis, M. MacCoss, S.S. Danyluk, J. Chem. Soc., Chem. Comm., 99, 536 (1984)
K-I. Asahi, K. Anzai, S. Suzuki, H. Iwasaki, Chem. Lett., 1197 (1973)
P.C. Manor, W. Saenger, D.B. Davies, K. Jankowski, A. Rabczenko, Biochim. Biophys. Acta 340, 472 (1974); L.T.J. Delbaere, M.N.G. James, Acta Cryst., Sec. B, 30, 1241 (1974)
Y. Yamagata, Fukumoto, S. Fujii, K-I. Tomita, T. Maruyama, M. Honjo, Acta Cryst., Sec. C, 39, 407 (1983)
S. Sugio, H. Mizuno, K. Kitamura, K. Hamada, M. Ikehara, H-I. Tomita, Acta Cryst., Sec. C, 39, 745 (1983)
M. Marton-Meresz, J. Kuszmann, I. Pelczer, L. Parkanyi, T. Koritsanszky, A. Kalman, Tetrahedron, 39, 275 (1983)
S. Sugio, H. Mizuno, K. Kitamura, K. Hamada, M. Ikehara, K-I. Tomita, Acta Cryst., Sec. C, 40, 712, (1984)
S.S. Mande, T.P. Seshadri, M.A. Viswamitra, Acta Cryst., Sec. C, 44, 138 (1988)
G.I. Birnbaum, M. Cygler, L. Dudycz, R. Stolarski, D. Shugar, D. Biochemistry, 20, 3294 (1981)
Author information
Authors and Affiliations
Corresponding author
About this article
Cite this article
Karwowski, B.T. Consequence of hydrogen atom abstraction from 5’-hydroxyl group of 2’-deoxyadenosine. Theoretical quantum mechanics study. cent.eur.j.chem. 6, 450–455 (2008). https://doi.org/10.2478/s11532-008-0038-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.2478/s11532-008-0038-z