JBC, Vol. 252, Issue 15, 5370-5371, Aug, 1977
Reaction of DNA with glycidaldehyde. Isolation and identification of a deoxyguanosine reaction product
B. L. Van Duuren and G. Loewengart
Glycidaldehyde, a bifunctional carcinogenic alkylating agent, has been
found to react with calf thymus DNA in vitro under alkaline conditions. A
product was isolated and identified to be the result of a fusion of a
delta4-imidazoline ring to the pyrimidine ring of deoxyguanosine at the N-1
and 2-NH2 positions. Following reaction and dialysis, the DNA was
hydrolyzed enzymatically to nucleosides. The structural assignment of the
product was based on comparison of the elution volume from a Sephadex G-10
column, the ultraviolet spectra at various conditions of pH, and the thin
layer chromatographic properties with respect to an authentic sample. The
formation of the extended ring system with DNA-derived guanosine may be
related to the mode of carcinogenic action of this difunctional alkylating
agent.
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