Literature DB >> 2831895

Unusual structural features of 2',3'-dideoxycytidine, an inhibitor of the HIV (AIDS) virus.

G I Birnbaum1, T S Lin, W H Prusoff.   

Abstract

The structure and conformation of 2',3'-dideoxycytidine, a potent inhibitor of the human immunodeficiency virus, was determined by X-ray crystallography. The nucleoside crystallizes in the tetragonal space group P4(1)2(1)2 with cell dimensions a = b = 8.698(4) and c = 26.155(9) A. Atomic parameters were refined by full-matrix least squares to a final value of R = 0.037 for 1926 observed reflections. The conformation of the furanose ring corresponds to the unusual C3'exo/C4'endo (3T4) pucker, similar to that found in one of the molecules of 3'-azidothymidine (AZT). The glycosidic torsion angle is also smaller than expected. The relevance of these unusual structural features to anti-AIDS activity is assessed.

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Year:  1988        PMID: 2831895     DOI: 10.1016/0006-291x(88)90637-7

Source DB:  PubMed          Journal:  Biochem Biophys Res Commun        ISSN: 0006-291X            Impact factor:   3.575


  5 in total

1.  Chemical reactivity analysis of deoxyribonucleosides and deoxyribonucleoside analogues (NRTIs): a first-principles density functional approach.

Authors:  Vipin Kumar; Shyam Kishor; Lavanya M Ramaniah
Journal:  J Mol Model       Date:  2012-03-21       Impact factor: 1.810

2.  In vitro and in vivo evidence that the antiviral activity of 2',3'-dideoxycytidine is target cell dependent in a feline retrovirus animal model.

Authors:  P J Polas; C L Swenson; R Sams; C M Cheney; K A Hayes; M J Tarr; G J Kociba; L E Mathes
Journal:  Antimicrob Agents Chemother       Date:  1990-07       Impact factor: 5.191

3.  Molecular modeling approach to understanding the mode of action of L-nucleosides as antiviral agents.

Authors:  K Lee; C K Chu
Journal:  Antimicrob Agents Chemother       Date:  2001-01       Impact factor: 5.191

4.  Correlation between preferred sugar ring conformation and activity of nucleoside analogues against human immunodeficiency virus.

Authors:  P Van Roey; J M Salerno; C K Chu; R F Schinazi
Journal:  Proc Natl Acad Sci U S A       Date:  1989-06       Impact factor: 11.205

5.  Molecular structures of two new anti-HIV nucleoside analogs: 9-(2,3-dideoxy-2-fluoro-beta-D-threo-pentofuranosyl)adenine and 9-(2,3-dideoxy-2-fluoro-beta-D-threo-pentofuranosyl)hypoxanthine.

Authors:  Y C Liaw; Y G Gao; V E Marquez; A H Wang
Journal:  Nucleic Acids Res       Date:  1992-02-11       Impact factor: 16.971

  5 in total

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