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Structures of the 2',3'-dideoxy and 2',3'-didehydro-2',3'-dideoxy analogs of tiazofurin. 1991

F T Burling, and B Gabrielsen, and B M Goldstein
Department of Biophysics, University of Rochester Medical Center, NY 14642.

2',3'-Dideoxytiazofurin [2-(2',3'-dideoxy-beta-D-glycero-pentafuranosyl)thiazole-4- carboxamide]hemihydrate (1), C9H12N2O3S.1/2H2O, Mr = 237.3, monoclinic, C2, a = 23.141 (2), b = 5.912 (1), c = 8.252 (1) A, beta = 90.71 (1) degrees, V = 1128.9 (4) A3, Z = 4, Dx = 1.396 g cm-3, Cu K alpha, lambda = 1.54178 A, mu = 25.0 cm-1, F(000) = 500, T = 295 K, R = 0.0319 for all 1316 unique reflections. 2',3'-Didehydro-2',3'-dideoxytiazofurin [2-(2',3'-dideoxy-beta-D-glyceropent-2-enofuranosyl)thiazole -4-carboxamide] (2), C9H10N2O3S, Mr = 226.3, orthorhombic, P2(1)2(1)2(1), a = 22.172 (2), b = 8.019 (1), c = 5.991 (1) A, V = 1065.2 (4) A3, Z = 4, Dx = 1.411 g cm-3, Cu K alpha, lambda = 1.54178 A, mu = 25.9 cm-1, F(000) = 472, T = 295 K, R = 0.0344 for all 957 unique reflections. Both structures show a close contact between the thiazole S and the pentose O(1') atoms. S...O(1') distances are 2.834 (2) A in (1) and 2.835 (1) A in (2), resulting from C-glycosidic torsion angles of 14.1 (2) and 5.2 (3) degrees respectively. This unusual feature is conserved in the crystal structures of other thiazole nucleosides [Goldstein, Mao & Marquez (1988). J. Med. Chem. 31, 1026-1031].

UI MeSH Term Description Entries
D003460 Crystallization The formation of crystalline substances from solutions or melts. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) Crystalline Polymorphs,Polymorphism, Crystallization,Crystal Growth,Polymorphic Crystals,Crystal, Polymorphic,Crystalline Polymorph,Crystallization Polymorphism,Crystallization Polymorphisms,Crystals, Polymorphic,Growth, Crystal,Polymorph, Crystalline,Polymorphic Crystal,Polymorphisms, Crystallization,Polymorphs, Crystalline
D012254 Ribavirin A nucleoside antimetabolite antiviral agent that blocks nucleic acid synthesis and is used against both RNA and DNA viruses. Ribovirin,Tribavirin,ICN-1229,Rebetol,Ribamide,Ribamidil,Ribamidyl,Ribasphere,Vilona,Viramide,Virazide,Virazole,ICN 1229,ICN1229
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
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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