A novel photoproduct of 2'-deoxyguanosine induced by acetone photosensitization: 8-(2,3,4-trihydroxybutyl)guanine.

Abstract

Acetone photosensitisation of 2'-deoxyguanosine in deaerated aqueous solution gives 8-(2,3,4-trihydroxybutyl)guanine as a major photoproduct. Its structure and that of its tetraacetate have been determined primarily by high resolution 1H NMR and mass spectrometry; a di-isopropylidene derivative has also been prepared. Mechanistic aspects of this novel photochemical transformation are discussed, particularly in relation to the alkaline cleavage of acetone photosensitised DNA at the sites of guanine bases.

• Authors: N D Sharma, R J Davies, D R Phillips, J A McCloskey
• Journal: Nucleic acids research (Nucleic Acids Res) Vol. 17 Issue 3 Pg. 955-67 (Feb 11 1989) ISSN: 0305-1048 [Print] England
• PMID: 2922279 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, P.H.S.)

Chemical References

• 8-(2,3,4-trihydroxybutyl)guanine
• Acetone
• Guanine
• Deoxyguanosine

Topics

• Acetone
• Acetylation
• Chromatography, High Pressure Liquid
• DNA Damage
• Deoxyguanosine (radiation effects)
• Guanine (analogs & derivatives, isolation & purification)
• Magnetic Resonance Spectroscopy
• Photochemistry
• Ultraviolet Rays