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@article{1129505, author = {Ponomareva, Alla and Yurenko, Yevgen and Zhurakivsky, Roman and van Mourik, Tanja and Hovorun, Dmytro}, article_location = {Philadelphia}, article_number = {5}, doi = {http://dx.doi.org/10.1080/07391102.2013.789401}, keywords = {2 ' 3 ' -didehydro-2' 3 ' -dideoxyadenosine; 2 ' 3 ' -didehydro-2 ' 3 ' -dideoxyguanosine; d4A; d4G; conformational analysis; hydrogen bonds; H-bonds; biological activity; nucleoside reverse transcriptase inhibitors; density functional theory}, language = {eng}, issn = {0739-1102}, journal = {Journal of Biomolecular Structure and Dynamics}, title = {Structural and energetic properties of the potential HIV-1 reverse transcriptase inhibitors d4A and d4G: a comprehensive theoretical investigation}, url = {http://www.tandfonline.com/doi/full/10.1080/07391102.2013.789401#.UoYzdScXeSk}, volume = {32}, year = {2014} }
TY - JOUR ID - 1129505 AU - Ponomareva, Alla - Yurenko, Yevgen - Zhurakivsky, Roman - van Mourik, Tanja - Hovorun, Dmytro PY - 2014 TI - Structural and energetic properties of the potential HIV-1 reverse transcriptase inhibitors d4A and d4G: a comprehensive theoretical investigation JF - Journal of Biomolecular Structure and Dynamics VL - 32 IS - 5 SP - 730-740 EP - 730-740 PB - Taylor & Francis SN - 07391102 KW - 2 ' 3 ' -didehydro-2' 3 ' -dideoxyadenosine KW - 2 ' 3 ' -didehydro-2 ' 3 ' -dideoxyguanosine KW - d4A KW - d4G KW - conformational analysis KW - hydrogen bonds KW - H-bonds KW - biological activity KW - nucleoside reverse transcriptase inhibitors KW - density functional theory UR - http://www.tandfonline.com/doi/full/10.1080/07391102.2013.789401#.UoYzdScXeSk L2 - http://www.tandfonline.com/doi/full/10.1080/07391102.2013.789401#.UoYzdScXeSk N2 - A comprehensive quantum-chemical investigation of the conformational landscapes of two nucleoside HIV-1 reverse transcriptase inhibitors, d4A and d4G, has been performed. Both nucleosides are shaped by a sophisticated network of specific noncovalent interactions, including conventional OH_O, NH_O and weak CH_O, CH_N hydrogen bonds, as well as dihydrogen CH_HC contacts. For the OH_O, NH_O, and CH_O hydrogen bonds, natural bond orbital analysis revealed hyperconjugative interactions between the oxygen lone pairs and the antibonding orbital of the donor group. For the CH _HC contacts, the electron density migrates from the antibonding orbital, corresponding to the CH group of the sugar residue, to the bonding orbital relative to the same group in the nucleobase. The results confirm the current belief that the biological activity of d4A and d4G is connected with the termination of the DNA chain synthesis. Thus, these nucleosides act as competitive HIV-1 reverse transcriptase inhibitors. ER -
PONOMAREVA, Alla, Yevgen YURENKO, Roman ZHURAKIVSKY, Tanja VAN MOURIK and Dmytro HOVORUN. Structural and energetic properties of the potential HIV-1 reverse transcriptase inhibitors d4A and d4G: a comprehensive theoretical investigation. \textit{Journal of Biomolecular Structure and Dynamics}. Philadelphia: Taylor \&{} Francis, 2014, vol.~32, No~5, p.~730-740. ISSN~0739-1102. Available from: https://dx.doi.org/10.1080/07391102.2013.789401.
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