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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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