Biomaterial Database

The solid-state and solution conformations of 2'-deoxy-2'-fluoro-4'-substituted nucleosides. 2021

Yanli Wang, and Shiqing Jiang, and Mingxiu Chang, and Chunhong Dong

Scientific Research Center, Henan University of Chinese Medicine, Zhengzhou, China.

The conformational features of drugs are important with respect to their biological activity. In this report, we confirmed the solid-state conformation of 1-(4'-azido-2'-deoxy-2'-fluoro-β-d-arabinofuranosyl) cytosine using single-crystal X-ray crystallography and the conformations of three 2'-deoxy-2'-fluoro-4'-substituted nucleosides in solution using Altona-Haasnoot's equations and Nuclear Overhauser effect spectroscopy (NOESY). Furthermore, we compared the preferred solid-state and solution conformation of these nucleosides with thermodynamics cycles to obtain more evidence of their conformations. The results showed 1-(4'-azido-2'-deoxy-2'-fluoro-β-d-arabinofuranosyl) cytosine was south type conformation (C-3'-exo) in solid-state and three 4'-substituted nucleosides were north type conformations (C-3'-endo) in solution. The north type conformations in solution indicated these compounds were steady to acidic and enzymatic N-glycolysis.

UI	MeSH Term	Description	Entries
D008958	Models, Molecular	Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures.	Molecular Models,Model, Molecular,Molecular Model
D008968	Molecular Conformation	The characteristic three-dimensional shape of a molecule.	Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D009705	Nucleosides	Purine or pyrimidine bases attached to a ribose or deoxyribose. (From King & Stansfield, A Dictionary of Genetics, 4th ed)	Nucleoside,Nucleoside Analog,Nucleoside Analogs,Analog, Nucleoside,Analogs, Nucleoside
D003596	Cytosine	A pyrimidine base that is a fundamental unit of nucleic acids.
D001386	Azides	Organic or inorganic compounds that contain the -N3 group.	Azide
D054879	Halogenation	Covalent attachment of HALOGENS to other compounds.	Bromination,Chlorination,Fluorination,Iodination,Iodation
D018360	Crystallography, X-Ray	The study of crystal structure using X-RAY DIFFRACTION techniques. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	X-Ray Crystallography,Crystallography, X Ray,Crystallography, Xray,X Ray Crystallography,Xray Crystallography,Crystallographies, X Ray,X Ray Crystallographies