Effect of structure of the carbohydrate fragment on homolytic cleavage on N-glycosidic and phosphate ester bonds in nucleosides and nucleotides
The relationships governing the formation of free purine bases and phosphate ions during the /gamma/-irradiation of dilute aqueous solutions of compounds of the adenosine and guanosine series were studied. The degree of cleavage of the N-glycosidic bond in the reaction of radical particles with nucleosides depends significantly on the structure of the carbohydrate component. The presence of free hydroxyl groups at the C/sup 2//prime/ atom of the initial substances facilitates cleavage of the N-glycosidic bond, whereas combination of the hydroxyls or their absence makes it more resistant to homolytic cleavage. The possibility of the formation of ortho- and metaphospate ions during free-radical transformations of nucleotides was demonstrated experimentally. Mechanisms are proposed for the observed transformations of the nucleosides and their derivatives on the basis of the obtained and published data.
- Research Organization:
- V.I. Lenin Belorussian State Univ., Minsk (USSR)
- OSTI ID:
- 5970600
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 24:5; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400600* -- Radiation Chemistry
ADENOSINE
AQUEOUS SOLUTIONS
AROMATICS
AZAARENES
CARBOHYDRATES
CHARGED PARTICLES
CHEMICAL BONDS
CHEMICAL RADIATION EFFECTS
CHEMISTRY
DISPERSIONS
DISSOCIATION
DISSOCIATION ENERGY
ELECTROMAGNETIC RADIATION
ENERGY
ESTERS
GAMMA RADIATION
GLYCOSIDES
GUANOSINE
HETEROCYCLIC COMPOUNDS
HYDROXYL RADICALS
IONIZATION
IONIZING RADIATIONS
IONS
IRRADIATION
MIXTURES
MOLECULAR IONS
MOLECULAR STRUCTURE
NUCLEOSIDES
NUCLEOTIDES
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC PHOSPHORUS COMPOUNDS
PHOSPHORIC ACID ESTERS
PURINES
RADIATION CHEMISTRY
RADIATION EFFECTS
RADIATIONS
RADICALS
RIBOSIDES
SOLUTIONS
STRUCTURAL CHEMICAL ANALYSIS