Isolation and characterization of pyrimidine-psoralen photoadducts from DNA

Journal Article · Wed May 06 00:00:00 EDT 1981 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00399a035· OSTI ID:6206181

Straub, K; Kanne, D; Hearst, J E; Rapoport, H

We have examined the photoadducts of 4'-hydroxymethyl-4,5',8-trimethylpsoralen (HMT) and native DNA. Five nucleoside-HMT monoaddition products have been isolated and characterized, corresponding to three deoxythymidine-HMT and two deoxyuridine (derived from deoxycytidine)-HMT adducts. Structural assignments are based on high resolution mass spectrometry and /sup 1/H NMR studies, including homonuclear spin decoupling and nuclear Overhauser effect (NOE) experiments. The results of this study indicate that (1) a limited number of nucleoside-psoralen adducts are formed with native, double-stranded DNA, and (2) the sterochemistry of the adducts is apparently determined by the geometry of the noncovalent intercalative complex formed by HMT and DNA prior to irradiation. 8 figures, 8 tables.

• Research Organization: Univ. of California, Berkeley
• OSTI ID: 6206181
• Journal Information: J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 103:9; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ADDUCTS
ANTICOAGULANTS
AZINES
COUMARINS
DNA
DRUGS
HEMATOLOGIC AGENTS
HETEROCYCLIC COMPOUNDS
MAGNETIC RESONANCE
MASS SPECTROSCOPY
NUCLEAR MAGNETIC RESONANCE
NUCLEIC ACIDS
NUCLEOSIDES
NUCLEOTIDES
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
OVERHAUSER EFFECT
PSORALEN
PYRIMIDINES
RESONANCE
RIBOSIDES
SPECTROSCOPY
STEREOCHEMISTRY