Conformations of Nucleoside Analogue 1-(2‘-Deoxy-β-d -ribofuranosyl)-1,2,4-triazole-3-carboxamide in Different DNA Sequence Contexts
| العنوان: | Conformations of Nucleoside Analogue 1-(2‘-Deoxy-β- |
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| المؤلفون: | Donald E. Bergstrom, Andy LiWang, Peiming Zhang, Douglas A. Klewer, Davisson Vj |
| المصدر: | Biochemistry. 40:1518-1527 |
| بيانات النشر: | American Chemical Society (ACS), 2001. |
| سنة النشر: | 2001 |
| مصطلحات موضوعية: | Circular dichroism, Stereochemistry, medicine.drug_class, Triazole, Carboxamide, Biochemistry, Nucleobase, chemistry.chemical_compound, Ribavirin, medicine, Phosphorus-31 NMR spectroscopy, Glycosides, Base Pairing, Nuclear Magnetic Resonance, Biomolecular, Circular Dichroism, Nucleic Acid Heteroduplexes, Temperature, Phosphorus Isotopes, Hydrogen Bonding, Sequence Analysis, DNA, Amides, Oligodeoxyribonucleotides, chemistry, Helix, Nucleic Acid Conformation, Thermodynamics, Protons, Two-dimensional nuclear magnetic resonance spectroscopy, DNA |
| الوصف: | The concept of using a dynamic base-pairing nucleobase as a mode for degenerate recognition presents a unique challenge to analysis of DNA structure. Proton and phosphorus NMR studies are reported for two nine-residue DNA oligodeoxyribonucleotides, d(CATGGGTAC).d(GTACNCATG) (1) and d(CATGTGTAC).(GTACNCATG) (2), which contained 1-(2'-deoxy-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide (N) in the center of the helix at position 14. The duplexes were compared to the canonical Watson-Crick duplexes, d(CATGGGTAC).d(GTACCCATG) (3) and d(CATGTGTAC).d(GTACACATG) (4). Two-dimensional NOESY spectra of 1-4 in H(2)O and D(2)O solutions collected at 5 degrees C allowed assignment of the exchangeable and nonexchangeable protons for all four oligodeoxyribonucleotides. Thermodynamic and circular dichroism data indicated that 1-4 formed stable, B-form duplexes at 5 degrees C. Two-dimensional (1)H-(31)P correlation spectra indicated that there were minor perturbations in the backbone only near the site of the triazole base. Strong NOESY cross-peaks were observed between the H5 and H1' of N14 in 1 and, unexpectedly, 2, which indicated that, in both duplexes, N14 was in the syn(chi)() conformation about the glycosidic bond. NOESY spectra of 1 and 2 recorded in 95% H(2)O, 5% D(2)O indicated that the imino proton of the base opposite N14, G5, or T5, formed a weak hydrogen bond with N14. These conformations place the polar carboxamide functional group in the major groove with motional averaging on the intermediate time scale. |
| تدمد: | 1520-4995 0006-2960 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::1aab6650400b55e7ca7c753b322c6488 https://doi.org/10.1021/bi001448f |
| رقم الأكسشن: | edsair.doi.dedup.....1aab6650400b55e7ca7c753b322c6488 |
| قاعدة البيانات: | OpenAIRE |
Find this issue from the American Chemical Society | تدمد: | 15204995 00062960 |
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