Biomaterial Database

Formation of cyclopyrimidines via the direct effects of gamma radiation of pyrimidine nucleosides. 1988

A A Shaw, and J Cadet

Département de Recherche Fondamentale, Centre d'Etudes Nucléaires de Grenoble, France.

Continuing our study of the direct effects of gamma radiation on DNA and its model compounds, we have isolated and characterized quantitatively an important lesion formed by irradiating pyrimidine 2'-deoxyribonucleosides in frozen aqueous solution. We report here the formation of 5',6-cyclo-5,6-dihydropyrimidine nucleosides via hydrogen abstraction at C5' of the osidic moiety with subsequent intramolecular attack at C6 of the base. We have so far managed to isolate six of the possible eight diastereomers of 5',6-cyclo-5,6-dihydrothymidine, and all four possible 5',6-cyclo-5,6-dihydro-2'-deoxyuridines formed by irradiation of 2'-deoxycytidine. Also presented is a detailed discussion of the configurational analysis of each isomer based on 1H NMR data.

UI	MeSH Term	Description	Entries
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
D009712	Nucleotides, Cyclic		Cyclic Nucleotide,Cyclic Nucleotides,Nucleotide, Cyclic
D011741	Pyrimidine Nucleosides	Pyrimidines with a RIBOSE attached that can be phosphorylated to PYRIMIDINE NUCLEOTIDES.	Nucleosides, Pyrimidine
D011743	Pyrimidines	A family of 6-membered heterocyclic compounds occurring in nature in a wide variety of forms. They include several nucleic acid constituents (CYTOSINE; THYMINE; and URACIL) and form the basic structure of the barbiturates.
D011854	Radiochemistry	The study of the chemical and physical phenomena of radioactive substances.	Radiochemistries
D005615	Freezing	Liquids transforming into solids by the removal of heat.	Melting
D005720	Gamma Rays	Penetrating, high-energy electromagnetic radiation emitted from atomic nuclei during NUCLEAR DECAY. The range of wavelengths of emitted radiation is between 0.1 - 100 pm which overlaps the shorter, more energetic hard X-RAYS wavelengths. The distinction between gamma rays and X-rays is based on their radiation source.	Gamma Wave,Gamma Radiation,Nuclear X-Rays,Radiation, Gamma,X-Rays, Nuclear,Gamma Radiations,Gamma Ray,Gamma Waves,Nuclear X Rays,Nuclear X-Ray,Ray, Gamma,Wave, Gamma,Waves, Gamma,X Rays, Nuclear,X-Ray, Nuclear
D012996	Solutions	The homogeneous mixtures formed by the mixing of a solid, liquid, or gaseous substance (solute) with a liquid (the solvent), from which the dissolved substances can be recovered by physical processes. (From Grant & Hackh's Chemical Dictionary, 5th ed)	Solution
D014867	Water	A clear, odorless, tasteless liquid that is essential for most animal and plant life and is an excellent solvent for many substances. The chemical formula is hydrogen oxide (H2O). (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	Hydrogen Oxide