Solution conformation of the N-(deoxyguanosin-8-yl)aminofluorene adduct opposite deoxyinosine and deoxyguanosine in DNA by NMR and computational characterization
Journal Article
·
· Chemical Research in Toxicology
- Columbia Univ., New York, NY (United States)
- Oak Ridge National Lab., TN (United States)
- New York Univ., NY (United States)
Two-dimensional proton NMR and energy minimization computations have been employed to characterize the conformations of the N-(deoxyguanosin-8-yl)aminofluorene adduct [(AF)G] positioned opposite deoxyguanosine in one, and opposite deoxyinosine in another DNA undecamer duplex in aqueous solution. The two oligomer duplexes used in this study are d[C1-C2-A3-T4-C5-(AF)G6-C7-T8-A9-C10-C11]{center_dot}[G12-G13-T14-A15-G16-X17-G18-A19-T20-G21-G22], where X17 was deoxyinosine in one duplex and deoxyguanosine in another. The exchangeable and nonexchangeable protons of the DNA are well resolved and narrow in the NMR spectra of the duplexes, and the base and sugar nucleic acid protons were assigned by NOESY and COSY data sets. All nine of the nonexchangeable aminofluorene ring protons were also assigned for the duplex that has deoxyinosine across from the modification site, and the (AF)G{center_dot}I structure was employed to model the (AF)G{center_dot}G one. The NOE distance restraints establish that the glycosidic torsion angle at (AF)G6 is syn. All other glycosidic torsion angles are anti, Watson-Crick type A{center_dot}T and G{center_dot}C base pairing is intact throughout the duplex except at the site of modification, and the helix maintains an overall B-DNA conformation. The syn orientation at the (AF)G6 places the aminofluorene ring in the B-DNA minor groove in a conformation similar to that found previously when the (AF)G was positioned opposite deoxyadenosine. 33 refs., 9 figs., 6 tabs.
- Sponsoring Organization:
- USDOE
- DOE Contract Number:
- FG02-90ER60931; AC05-84OR21400
- OSTI ID:
- 502032
- Journal Information:
- Chemical Research in Toxicology, Journal Name: Chemical Research in Toxicology Journal Issue: 3 Vol. 8; ISSN 0893-228X; ISSN CRTOEC
- Country of Publication:
- United States
- Language:
- English
Similar Records
Solution conformation of [AF]dG opposite a - 1 deletion site in a DNA duplex: Intercalation of the covalently attached aminofluorene ring into the Helix with base development of the C{sup 8}-modified syn guanine into the major groove
Solution conformation of the N-(deoxyguanosin-8-yl)-1-aminopyrene ([AP]dG) adduct opposite dC in a DNA duplex
Solution conformation of the (-)-cis-anti-benzo[a]-pyrenyl-dG adduct opposite dC in a DNA duplex: Intercalation of the covalently attached BP ring into the helix with base displacement of the modified deoxyguanosine into the major groove
Journal Article
·
Tue May 09 00:00:00 EDT 1995
· Biochemistry (Eaton)
·
OSTI ID:415078
Solution conformation of the N-(deoxyguanosin-8-yl)-1-aminopyrene ([AP]dG) adduct opposite dC in a DNA duplex
Journal Article
·
Tue Oct 01 00:00:00 EDT 1996
· Biochemistry (Eaton)
·
OSTI ID:508206
Solution conformation of the (-)-cis-anti-benzo[a]-pyrenyl-dG adduct opposite dC in a DNA duplex: Intercalation of the covalently attached BP ring into the helix with base displacement of the modified deoxyguanosine into the major groove
Journal Article
·
Tue Jul 30 00:00:00 EDT 1996
· Biochemistry (Eaton)
·
OSTI ID:490280