Structures of acrolein-guanine adducts: a semi-empirical self-consistent field and nuclear magnetic resonance spectral study

Chemical Research in Toxicology
D W BoerthC Hoffman

Abstract

The structures and conformations of adducts formed by reaction of guanosine with several mutagenic alpha,beta-unsaturated carbonyl compounds have been investigated by semi-empirical molecular orbital calculations and compared with NMR spectral results. Two cyclization processes taking place on the pyrimidine ring of guanine leading to two sets of regioisomers, 11-hydroxy- and 13-hydroxytetrahydropyrimidinoguanines (THPG), were considered. Relative stabilities and geometries of all configurations and conformations of adducts with acrolein, crotonaldehyde, and alpha-chloroacrolein were calculated by PM3, AM1, and MNDO methods. PM3 results were the most compatible with experimental structures based on 400-MHz 1H NMR spectroscopy. The most stable structures for the 11-hydroxy and 13-hydroxy THPG isomers from acrolein are predicted to have chair-like structures for the tetrahydropyrimidine ring and axial hydroxyl groups, as suggested by the NMR spectra of the isolated adducts. Of the possible isomers from guanine and crotonaldehyde, cis-11-hydroxy-13-methyl THPG with methyl and hydroxyl groups axial is predicted to be the most stable. The only isolated adduct is the trans-13-hydroxy-11-methyl THPG with methyl shown to be equatorial ...Continue Reading

References

Jun 1, 1990·Journal of Applied Toxicology : JAT·C DeiningerC Hoffman
Nov 1, 1994·Chemical Research in Toxicology·H J Chen, F L Chung
Aug 2, 1994·Proceedings of the National Academy of Sciences of the United States of America·R G Nath, F L Chung
Jan 1, 1996·Chemical Research in Toxicology·G R Reddy, L J Marnett

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Citations

Jun 1, 2002·Environmental Science & Technology·Hugo DestaillatsM Judith Charles
Jul 25, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ekaterina A VerochkinaIgor B Rozentsveig
May 11, 2006·Environmental Science & Technology·Seok-Young OhPei C Chiu

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