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PNAS | June 15, 1970 | vol. 66 | no. 2 | 488-494
Copyright © 1970 by the National Academy of Sciences

Coding and Conformational Properties of Oligonucleotides Modified with the Carcinogen N-2-acetylaminofluorene

Dezider Grunberger, James H. Nelson, Charles R. Cantor, and I. Bernard Weinstein

The present studies were undertaken to determine the mechanism by which attachment of the carcinogen N-2-acetylaminofluorene to guanosine residues in nucleic acids distorts their structure and function. Oligonucleotides were modified with N-acetoxy-2-acetylaminofluorene, repurified, and their base compositions analyzed. Evidence is presented that acetylaminofluorene residues bound to guanosines in GpUpU, ApApG, or poly (U,G) inactivates their function in codon recognition. Circular dichroism spectra suggest that this is caused by gross conformational changes in these compounds involving both a rotation about the glycosidic bond of guanosine residues bearing N-2-acetylaminofluorene, as well as stacking interactions between the drug and bases adjacent to the substituted guanosine.
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