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Structure of 3'-azido-3'-deoxythymidine, AZT. 1988

I Dyer, and J N Low, and P Tollin, and H R Wilson, and R A Howie
Carnegie Laboratory of Physics, University of Dundee, Scotland.

C10H13N5O4, Mr = 267.2, monoclinic, P2(1), a = 5.716 (3), b = 11.998 (8), c = 17.658 (10) A, beta = 94.26 (4) degrees, V = 1208 A3, Z = 4, D chi = 1.47 g cm-3, lambda (Mo K alpha) = 0.71069 A, mu = 7.5 cm-1, F(000) = 560, T = 293 K. R = 0.060 for 2138 unique observed [F greater than 4 sigma (F)] reflections. The N-glycosidic torsion angles chi have values -125.9 (5) and -172.0 (5) degrees, in the anti range. (Molecule-A values are given first throughout.) The sugar puckers are 2(3)T (C3'-exo/C2'-endo), with P = 171 (1) degrees and psi m = 14 (1) degrees, and 4(3)T (C4'-endo/C3'-exo), with P = 213 (1) degrees and psi m = 11 (1) degrees. The C4-C5 conformations, with gamma = 49.7 (5) and 173.7 (5) degrees, are + sc (gauche-gauche) and ap (gauche-trans). The conformational parameters used follow the guidelines of the IUPAC-IUB Joint Commission on Biochemical Nomenclature [Pure Appl. Chem. (1983), 55, 1273-1280]. The molecules in the asymmetric unit form a hydrogen-bonded, base-paired dimer. The bonding is as follows: N3A-0.973 A-H3A... 1.790 A...O2B, N3A...O2B 2.747 (8) A, angle at H3A 167 degrees and N3B-0.992 A-H3B...1.916 A...O2A, N3B...O2A 2.894 (8) A, angle at H3B 168 degrees. The propeller twist between the bases is 5 degrees [Wilson & Tollin (1987). Nucleosides Nucleotides, 6, 643-653].

UI MeSH Term Description Entries
D014961 X-Ray Diffraction The scattering of x-rays by matter, especially crystals, with accompanying variation in intensity due to interference effects. Analysis of the crystal structure of materials is performed by passing x-rays through them and registering the diffraction image of the rays (CRYSTALLOGRAPHY, X-RAY). (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) Xray Diffraction,Diffraction, X-Ray,Diffraction, Xray,Diffractions, X-Ray,Diffractions, Xray,X Ray Diffraction,X-Ray Diffractions,Xray Diffractions
D015215 Zidovudine A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia. AZT (Antiviral),Azidothymidine,3'-Azido-2',3'-Dideoxythymidine,3'-Azido-3'-deoxythymidine,AZT Antiviral,AZT, Antiviral,BW A509U,BWA-509U,Retrovir,3' Azido 2',3' Dideoxythymidine,3' Azido 3' deoxythymidine,Antiviral AZT,BWA 509U,BWA509U
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

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