X-ray analysis of 2',3'-lyxoanhydrothymidine, a conformationally restricted inhibitor of retroviral reverse transcriptases.
2',3'-Lyxoanhydrothymidine (LAT), a conformationally restricted inhibitor of retroviral reverse transcriptases, has been studied by X-ray analysis. The unit cell contains two crystallographically independent molecules A and B. Their sugar moieties have an identical structure: an 04'-endo pucker of the furanose cycle and a trans conformation about the exocyclic C4'-C5' bond. The conformations of A and B molecules differ with respect to the N-glycosidic bond: chi A(04 'Cl' N1C2) = -121.9 degrees which is typical of a common anti conformation whereas chi B (04'Cl'N1C2) = 121.2 degrees corresponds to a rare high-syn conformation. All the conformation properties of LAT molecules stem from the presence of an epoxide cycle in their molecules.
V.A. Engelhardt Institute of Molecular Biology, USSR Academy of Sciences, Moscow.
G V
GV
Gurskaya
A V
AV
Bochkarev
A S
AS
Zdanov
A V
AV
Papchikhin
P P
PP
Purygin
A A
AA
Krayevsky
D000998:Antiviral Agents; D008958:Models, Molecular; D008968:Molecular Conformation; D012190:Retroviridae / Q000201:enzymology*; D018894:Reverse Transcriptase Inhibitors; D013936:Thymidine / Q000031:analogs & derivatives* / Q000494:pharmacology; D014961:X-Ray Diffraction
D000998:Antiviral Agents; D018894:Reverse Transcriptase Inhibitors; C064864:2',3'-anhydrothymidine; D013936:Thymidine