Please use this identifier to cite or link to this item: http://hdl.handle.net/1959.3/61883

Download PDF (Published version) (Adobe Acrobat PDF, -1 bytes)

Title

Electronic structure of the azide group in 3 '-azido-3 '-deoxythymidine (AZT) compared to small azide compounds

Author(s)

Chen, Fang-Fang;  Wang, Feng

Abstract

Theoretical calculations for some structural and electronic properties of the azide moiety in the nucleoside reverse transcriptase (RT) inhibitor 3'-azido-3'-deoxythymidine (AZT) are reported. These properties, which include geometrical properties in three dimensional space, Hirshfeld charges, electrostatic potential (MEP), vibrational frequencies, and core and valence ionization spectra, are employed to study how the azide group is affected by the presence of a larger fragment. For this purpose, two small but important organic azides, hydrazoic acid and methyl azide, are also considered. The general features of trans Cs configuration for RNNN fragments[1] is distorted in the large AZT bio-molecule. Hirshfeld charge analysis shows charges are reallocated more evenly on azide when the donor group R is not a single atom. Infrared and photoelectron spectra reveal different aspects of the compounds. In conclusion, the electronic structural properties of the compounds depend on the specific property, the local structure and chemical environment of a species.

Publication type

Journal article

Research centre

Swinburne University of Technology. Faculty of Information and Communication Technologies. Centre for Molecular Simulation

Source

Molecules, Vol. 14, no. 7 (Jul 2009), pp. 2656-2668

Publication year

2009

FOR Code(s)

0304 Medicinal and Biomolecular Chemistry

Keyword(s)

Azide;  Azidothymidine;  Electronic structures;  Density functional theory

Publisher

Molecular Diversity Preservation International (MDPI)

ISSN

1420-3049

Publisher URL

http://dx.doi.org/10.3390/molecules14072656

Copyright

Copyright © 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). Published version of the paper reproduced here in accordance with this copyright policy.

Full text

Peer reviewed