Electronic Structure of the Azide Group in 3′-Azido-3′-deoxythymidine (AZT) Compared to Small Azide Compounds

Molecules

Fang-Fang Chen¹ 

[1] Centre for Molecular Simulation, Swinburne University of Technology, P. O. Box 218, Hawthorn, Melbourne, Victoria, 3122, Australia;

关键词: azide;    azidothymidine;    electronic structures;    density functional theory;   

DOI  :  10.3390/molecules14072656

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland.