Structure of a hydroxyl radical induced cross-link of thymine and tyrosine

Journal Article · Tue Aug 23 04:00:00 EDT 1988 · Biochemistry; (United States)

DOI:https://doi.org/10.1021/bi00417a024· OSTI ID:6267456

Margolis, S A; Coxon, B; Gajewski, E; Dizdaroglu, M

DNA-protein cross-links are formed when living cells or isolated chromatin is exposed to ionizing radiation. Little is known about the actual cross-linked products of DNA and proteins. In this work, a novel hydroxyl radical induced cross-link of thymine and tyrosine has been isolated along with a tyrosine dimer by high-performance liquid chromatography of aqueous mixtures of tyrosine and thymine that had been exposed to hydroxyl radicals generated by ionizing radiation. The isolated compounds have been examined by gas chromatography-mass spectrometry, high-resolution mass spectrometry, and /sup 1/H and /sup 13/C nuclear magnetic resonance spectroscopy. The structure of the thymine-tyrosine cross-link has been identified as the product from the formation of a covalent bond between the methyl group of the thymine and carbon 3 of the tyrosine ring. In addition, the 3,3' tyrosine dimer was isolated and characterized. The mechanism of the formation of these compounds is discussed. This work presents the first complete chemical characterization of a hydroxyl radical induced DNA base-amino acid cross-link.

• Research Organization: National Bureau of Standards, Gaithersburg, MD (USA)
• OSTI ID: 6267456
• Journal Information: Biochemistry; (United States), Journal Name: Biochemistry; (United States) Vol. 27:17; ISSN BICHA
• Country of Publication: United States
• Language: English

Related Subjects

550601 -- Medicine-- Unsealed Radionuclides in Diagnostics
560120* -- Radiation Effects on Biochemicals
Cells
& Tissue Culture
62 RADIOLOGY AND NUCLEAR MEDICINE
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
AMINO ACIDS
AZINES
BARYONS
BETA DECAY RADIOISOTOPES
BETA-MINUS DECAY RADIOISOTOPES
BIOLOGICAL EFFECTS
BIOLOGICAL RADIATION EFFECTS
CARBON 13
CARBON ISOTOPES
CARBOXYLIC ACIDS
CHEMICAL REACTIONS
CHROMATOGRAPHY
COBALT 60
COBALT ISOTOPES
CROSS-LINKING
DNA
ELECTROMAGNETIC RADIATION
ELEMENTARY PARTICLES
EVEN-ODD NUCLEI
FERMIONS
GAMMA RADIATION
GAS CHROMATOGRAPHY
HADRONS
HETEROCYCLIC COMPOUNDS
HYDROXY ACIDS
HYDROXY COMPOUNDS
HYDROXYL RADICALS
INTERMEDIATE MASS NUCLEI
INTERNAL CONVERSION RADIOISOTOPES
IONIZING RADIATIONS
ISOMERIC TRANSITION ISOTOPES
ISOTOPES
LIGHT NUCLEI
LIQUID COLUMN CHROMATOGRAPHY
MAGNETIC RESONANCE
MASS SPECTROSCOPY
MINUTES LIVING RADIOISOTOPES
NUCLEAR MAGNETIC RESONANCE
NUCLEI
NUCLEIC ACIDS
NUCLEONS
ODD-ODD NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
POLYMERIZATION
PROTONS
PYRIMIDINES
RADIATION EFFECTS
RADIATIONS
RADICALS
RADIOINDUCTION
RADIOISOTOPES
RESONANCE
SEPARATION PROCESSES
SPECTROSCOPY
STABLE ISOTOPES
THYMINE
TYROSINE
URACILS
YEARS LIVING RADIOISOTOPES