Photochemistry of cytosine derivatives. I. Photochemistry of thymidylyl-(3'. -->. 5')-deoxycytidine. [Uv radiation]
Journal Article
·
· Biochemistry; (United States)
OSTI ID:6591812
The photochemistry of thymidylyl-(3' ..-->.. 5')-deoxycytidine (dTpdC) was studied as a model system of adjacent thymine and cytosine bases in DNA. Acetophenone-sensitized irradiation causes the cytosine moiety in dTpdC to react with the thymine moiety intramolecularly. Three unstable photoproducts are formed initially which are converted into three isomeric dinucleoside phosphates of thymine-uracil cyclobutane photodimer in a ratio of 4.2:2.2:1. Under the same irradiation condition thymidylyl-(3' ..-->.. 5')-thymidine (dTpdT) yields two products in a ratio of 6:1. The structures of these products are established by chemical and spectroscopic methods. The major product in these reactions has been identified as the stereoisomer which has the same anti,anti relationship between the pyrimidine rings and the deoxyribose group as in the parent dinucleoside phosphates. The efficiency of the intramolecular dimerization of dTpdC is about one-third that of dTpdT. The results suggest that the cytosine base in DNA may be converted to a uracil base via photodimerization with an adjacent pyrimidine base, hydrolysis, and photoreactivation.
- Research Organization:
- Univ. of Chicago, IL
- OSTI ID:
- 6591812
- Journal Information:
- Biochemistry; (United States), Journal Name: Biochemistry; (United States) Vol. 17:23; ISSN BICHA
- Country of Publication:
- United States
- Language:
- English
Similar Records
Human repair endonuclease incises DNA at cytosine photoproducts
Nuclear magnetic resonance studies of cis-syn, trans-syn, and 6-4 photodimers of thymidylyl(3'-5')thymidine monophosphate and cis-syn photodimers of thymidylyl(3'-5')thymidine cyanoethyl phosphotriester
Formation of cyclobutane thymine dimers photosensitized by pyridopsoralens: Quantitative and qualitative distribution within DNA
Conference
·
Fri May 01 00:00:00 EDT 1987
· Fed. Proc., Fed. Am. Soc. Exp. Biol.; (United States)
·
OSTI ID:6019840
Nuclear magnetic resonance studies of cis-syn, trans-syn, and 6-4 photodimers of thymidylyl(3'-5')thymidine monophosphate and cis-syn photodimers of thymidylyl(3'-5')thymidine cyanoethyl phosphotriester
Journal Article
·
Tue Jul 26 00:00:00 EDT 1988
· Biochemistry; (United States)
·
OSTI ID:6828116
Formation of cyclobutane thymine dimers photosensitized by pyridopsoralens: Quantitative and qualitative distribution within DNA
Journal Article
·
Tue Jul 23 00:00:00 EDT 1991
· Biochemistry; (United States)
·
OSTI ID:5045966
Related Subjects
550200* -- Biochemistry
59 BASIC BIOLOGICAL SCIENCES
AMINES
AZINES
BIOCHEMICAL REACTION KINETICS
BIOLOGICAL EFFECTS
BIOLOGICAL RADIATION EFFECTS
BIOLOGICAL RECOVERY
BIOLOGICAL REPAIR
CHEMICAL REACTIONS
CHEMISTRY
CYTOSINE
DIMERIZATION
ELECTROMAGNETIC RADIATION
HETEROCYCLIC COMPOUNDS
HYDROXY COMPOUNDS
KINETICS
NUCLEOTIDES
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PHOTOCHEMISTRY
PHOTOREACTIVATION
POLYMERIZATION
PYRIMIDINES
RADIATION EFFECTS
RADIATIONS
REACTION KINETICS
RECOVERY
REPAIR
THYMINE
ULTRAVIOLET RADIATION
URACILS
59 BASIC BIOLOGICAL SCIENCES
AMINES
AZINES
BIOCHEMICAL REACTION KINETICS
BIOLOGICAL EFFECTS
BIOLOGICAL RADIATION EFFECTS
BIOLOGICAL RECOVERY
BIOLOGICAL REPAIR
CHEMICAL REACTIONS
CHEMISTRY
CYTOSINE
DIMERIZATION
ELECTROMAGNETIC RADIATION
HETEROCYCLIC COMPOUNDS
HYDROXY COMPOUNDS
KINETICS
NUCLEOTIDES
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PHOTOCHEMISTRY
PHOTOREACTIVATION
POLYMERIZATION
PYRIMIDINES
RADIATION EFFECTS
RADIATIONS
REACTION KINETICS
RECOVERY
REPAIR
THYMINE
ULTRAVIOLET RADIATION
URACILS