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Radiolysis of aqueous solutions of nucleosides halogenated at the sugar moiety

Abstract

The pulse radiolysis of aqueous solutions of nucleosides halogenated at the sugar moiety (2'-bromo-2'-deoxyuridine 4, 3'-deoxy-3'-iodothymidine 5, 5'-deoxy-5'-iodouridine 6) has been studied. G(Hal) were determined by conductometry varying the experimental conditions (pH, saturation with Ar, N/sub 2/O or air, addition of t-butanol). The results indicate that solvated electrons both add to the nucleobases and eliminate halogen ions from the halogenated sugar moiety. In the case of 4(and possibly of 5) the radical anion of the base transfers (k approximately 10/sup 5/s/sup -1/) an electron to the sugar-bound halogen atom thus cleaving the C-Hal bond. In competition with this reaction there is a protonation of the radical anion of the base by protons and by water. For the latter reaction constant of k = 5 x 10/sup 3/ M/sup -1/s/sup -1/ was estimated. Compound 4 has also been investigated by product analysis after 60-Co-..gamma..-irradiation. In aerated solutions erythrose is formed with a G-value of 0.12. Its precursor radical is the 2'-radical generated from 4 by dissociative electron capture which reacts with O/sub 2/ to the corresponding peroxyl radical. Erythrose is formed after a sequence of reactions, one of which involves the scission of the C-1'-C-2'bond. Under this condition G(HBr) as measured  More>>
Authors:
Hissung, A; Isildar, M; von Sonntag, C; [1]  Witzel, H [2] 
  1. Max-Planck-Institut fuer Kohlenforschung, Muelheim an der Ruhr (Germany, F.R.). Inst. fuer Strahlenforschung
  2. Biochemisches Institut der Westfaelischen Wilhelms-Universitaet, Muenster, West Germany
Publication Date:
Feb 01, 1981
Product Type:
Journal Article
Reference Number:
AIX-12-609950; EDB-81-131947
Resource Relation:
Journal Name: Int. J. Radiat. Biol. Relat. Stud. Phys., Chem. Med.; (United Kingdom); Journal Volume: 39:2
Subject:
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.; BUDR; RADIOLYSIS; IODODEOXYURIDINE; THYMIDINE; AQUEOUS SOLUTIONS; ARGON; BUTANOLS; COBALT 60; G VALUE; GAMMA RADIATION; HALOGEN COMPOUNDS; NITROGEN OXIDES; OXYGEN; PH VALUE; PULSED IRRADIATION; RESPONSE MODIFYING FACTORS; SACCHARIDES; SOLVATED ELECTRONS; ALCOHOLS; ANTIMETABOLITES; AZINES; BETA DECAY RADIOISOTOPES; BETA-MINUS DECAY RADIOISOTOPES; BROMOURACILS; CARBOHYDRATES; CHALCOGENIDES; CHEMICAL RADIATION EFFECTS; CHEMICAL REACTIONS; CHEMISTRY; COBALT ISOTOPES; DECOMPOSITION; DISPERSIONS; DRUGS; ELECTROMAGNETIC RADIATION; ELECTRONS; ELEMENTARY PARTICLES; ELEMENTS; FERMIONS; FLUIDS; GASES; HETEROCYCLIC COMPOUNDS; HYDROXY COMPOUNDS; INTERMEDIATE MASS NUCLEI; INTERNAL CONVERSION RADIOISOTOPES; IODOURACILS; IONIZING RADIATIONS; IRRADIATION; ISOMERIC TRANSITION ISOTOPES; ISOTOPES; LEPTONS; MINUTES LIVING RADIOISOTOPES; MIXTURES; NITROGEN COMPOUNDS; NONMETALS; NUCLEI; NUCLEOSIDES; NUCLEOTIDES; ODD-ODD NUCLEI; ORGANIC BROMINE COMPOUNDS; ORGANIC COMPOUNDS; ORGANIC HALOGEN COMPOUNDS; ORGANIC IODINE COMPOUNDS; ORGANIC NITROGEN COMPOUNDS; OXIDES; OXYGEN COMPOUNDS; PYRIMIDINES; RADIATION CHEMISTRY; RADIATION EFFECTS; RADIATIONS; RADIOISOTOPES; RARE GASES; RIBOSIDES; SOLUTIONS; URACILS; YEARS LIVING RADIOISOTOPES; 560111* - Radiation Effects on Biochemicals- In Vitro- (-1987)
OSTI ID:
6360862
Country of Origin:
United Kingdom
Language:
English
Other Identifying Numbers:
Journal ID: CODEN: IJRBA
Submitting Site:
INIS
Size:
Pages: 185-193
Announcement Date:
Jul 01, 1981

Citation Formats

Hissung, A, Isildar, M, von Sonntag, C, and Witzel, H. Radiolysis of aqueous solutions of nucleosides halogenated at the sugar moiety. United Kingdom: N. p., 1981. Web. doi:10.1080/09553008114550201.
Hissung, A, Isildar, M, von Sonntag, C, & Witzel, H. Radiolysis of aqueous solutions of nucleosides halogenated at the sugar moiety. United Kingdom. doi:10.1080/09553008114550201.
Hissung, A, Isildar, M, von Sonntag, C, and Witzel, H. 1981. "Radiolysis of aqueous solutions of nucleosides halogenated at the sugar moiety." United Kingdom. doi:10.1080/09553008114550201. https://www.osti.gov/servlets/purl/10.1080/09553008114550201.
@misc{etde_6360862,
title = {Radiolysis of aqueous solutions of nucleosides halogenated at the sugar moiety}
author = {Hissung, A, Isildar, M, von Sonntag, C, and Witzel, H}
abstractNote = {The pulse radiolysis of aqueous solutions of nucleosides halogenated at the sugar moiety (2'-bromo-2'-deoxyuridine 4, 3'-deoxy-3'-iodothymidine 5, 5'-deoxy-5'-iodouridine 6) has been studied. G(Hal) were determined by conductometry varying the experimental conditions (pH, saturation with Ar, N/sub 2/O or air, addition of t-butanol). The results indicate that solvated electrons both add to the nucleobases and eliminate halogen ions from the halogenated sugar moiety. In the case of 4(and possibly of 5) the radical anion of the base transfers (k approximately 10/sup 5/s/sup -1/) an electron to the sugar-bound halogen atom thus cleaving the C-Hal bond. In competition with this reaction there is a protonation of the radical anion of the base by protons and by water. For the latter reaction constant of k = 5 x 10/sup 3/ M/sup -1/s/sup -1/ was estimated. Compound 4 has also been investigated by product analysis after 60-Co-..gamma..-irradiation. In aerated solutions erythrose is formed with a G-value of 0.12. Its precursor radical is the 2'-radical generated from 4 by dissociative electron capture which reacts with O/sub 2/ to the corresponding peroxyl radical. Erythrose is formed after a sequence of reactions, one of which involves the scission of the C-1'-C-2'bond. Under this condition G(HBr) as measured by pulse radiolysis is 0.8. Thus erythrose is formed in 15 per cent yield with respect to its precursor radical. This result is of importance in assessing the precursor radical of a similar product observed in irradiated DNA.}
doi = {10.1080/09553008114550201}
journal = {Int. J. Radiat. Biol. Relat. Stud. Phys., Chem. Med.; (United Kingdom)}
volume = {39:2}
journal type = {AC}
place = {United Kingdom}
year = {1981}
month = {Feb}
}