Document 0886
 DOCN  M9590886
 TI    [X-ray structural study of 3'-O-methylthiomethylthymidine and
       3'-O-methylsulfinylmethylthymidine--potential inhibitors of HIV]
 DT    9509
 AU    Bochkarev AV; Zavgorodnii SG; Zhdanov AS; Gurskaia GV
 SO    Bioorg Khim. 1995 Mar;21(3):206-11. Unique Identifier : AIDSLINE
       MED/95283616
 AB    The molecular and crystalline structures of deoxiribonucleoside analogs:
       3'-O-methylthiomethylthymidine monohydrate dT(CH2SMe).H2O and
       3'-O-methylsulphinylmethylthymidine dT(CH2SOMe) were determined. The
       space group of dT(CH2SMe).H2O crystals is P2(1), the parameters of the
       elementary cell are a = 10.417(1), b = 4.912(2), c = 15.969(2) A, beta =
       107.23(1) degrees, V = 780.5 A3, Z = 2, R = 3.8%. The crystals of
       dT(CH2SOMe have a space group P2(1)2(1)2(1), the elementary cell
       parameters are a = 8.858(2), b = 9.303(1), c = 17.698(2) A, V = 1458.3
       A3, Z = 4, R = 2.8%. The dT(CH2SMe) and dT(CH2SOMe) molecules are
       characterized by an anti-conformation relative to the glycoside bond
       (angles chi (O4'-C1'-N1-C2) are equal to 116.2 degrees and -148.8
       degrees), a gauche(+)-conformation relative to the exocyclic bond
       C4'-C5' (angles phi CO (C3'-C4'-C5'-O5') are equal to 52.1 degrees and
       41.1 degrees). The conformation of the furanose cycle in the dT(CH2SMe)
       molecule is described by C2'-endo-C3'-exo (P = 167.8 degrees, psi m =
       34.8 degrees) and in the dT(CH2SOMe) molecule by C2'-endo-C1'-exo (P =
       148.4 degrees, psi m = 35.4 degrees). The structures studied were
       compared with 3'-azido-3'-deoxythymidine (AZT) and thymidine.
 DE    Antiviral Agents/*CHEMISTRY/PHARMACOLOGY  English Abstract  HIV/*DRUG
       EFFECTS  Nucleic Acid Conformation  Thymidine/*ANALOGS &
       DERIVATIVES/CHEMISTRY/PHARMACOLOGY  X-Ray Diffraction  JOURNAL ARTICLE

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