Unusual structural features of 2',3'-dideoxycytidine, an inhibitor of the HIV (AIDS) virus.
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.
Birnbaum
G I
GI
Division of Biological Sciences, National Research Council of Canada, Ottawa, Canada.
Lin
T S
TS
Prusoff
W H
WH
D000163:Acquired Immunodeficiency Syndrome / Q000188:drug therapy; D055598:Chemical Phenomena; D002621:Chemistry; D003461:Crystallography; D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000032:analysis / Q000494:pharmacology; D006678:HIV / Q000187:drug effects*; D008958:Models, Molecular; D008968:Molecular Conformation; D016047:Zalcitabine
D003841:Deoxycytidine; D016047:Zalcitabine