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Chemical and structural characterization of interstrand cross-links formed between abasic sites and adenine residues in duplex DNA.

Price NE, Catalano MJ, Liu S, Wang Y, Gates KS - Nucleic Acids Res. (2015)

Bottom Line: A synthetic standard was prepared for the putative nucleoside cross-link remnant 6 in which the anomeric carbon of the 2-deoxyribose residue was connected to the exocyclic N(6)-amino group of dA.These findings establish the chemical structure of the dA-Ap cross-link released from duplex DNA and may provide methods for the detection of this lesion in cellular DNA.Both the nucleoside cross-link remnant 6: and the cross-link in duplex DNA were quite stable at pH 7 and 37°C, suggesting that the dA-Ap cross-link could be a persistent lesion with the potential to block the action of various DNA processing enzymes.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Missouri, 125 Chemistry Building, Columbia, MO 65211, USA.

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TOCSY data showing the N6-H correlations with H1″ protons of compound 6. The correlations between the N6-H of dA and H1″ of dR can be seen by contours shown at the intersecting lines between signals for the N6-H and H1″ protons, indicating these protons are in the same spin system.
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Figure 4: TOCSY data showing the N6-H correlations with H1″ protons of compound 6. The correlations between the N6-H of dA and H1″ of dR can be seen by contours shown at the intersecting lines between signals for the N6-H and H1″ protons, indicating these protons are in the same spin system.

Mentions: The NMR data provided evidence that the anomeric carbon of the 2-deoxyribose adduct was attached at the exocyclic N6-amino group of the 2′-deoxyadenosine unit, as shown in structure 6. For example, an 15N-HMBC experiment revealed three-bond coupling between the N6-nitrogen and the H2″ protons of the 2-deoxyribose adduct (Figure 3). Furthermore, the TOCSY spectra showed that the N6-H, the H1″ and H2″ protons reside in the same spin system (Figure 4). Overall, the NMR analysis established that the reaction of dA with 2-deoxyribose provided the desired cross-link remnant 6.


Chemical and structural characterization of interstrand cross-links formed between abasic sites and adenine residues in duplex DNA.

Price NE, Catalano MJ, Liu S, Wang Y, Gates KS - Nucleic Acids Res. (2015)

TOCSY data showing the N6-H correlations with H1″ protons of compound 6. The correlations between the N6-H of dA and H1″ of dR can be seen by contours shown at the intersecting lines between signals for the N6-H and H1″ protons, indicating these protons are in the same spin system.
© Copyright Policy - creative-commons
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4402519&req=5

Figure 4: TOCSY data showing the N6-H correlations with H1″ protons of compound 6. The correlations between the N6-H of dA and H1″ of dR can be seen by contours shown at the intersecting lines between signals for the N6-H and H1″ protons, indicating these protons are in the same spin system.
Mentions: The NMR data provided evidence that the anomeric carbon of the 2-deoxyribose adduct was attached at the exocyclic N6-amino group of the 2′-deoxyadenosine unit, as shown in structure 6. For example, an 15N-HMBC experiment revealed three-bond coupling between the N6-nitrogen and the H2″ protons of the 2-deoxyribose adduct (Figure 3). Furthermore, the TOCSY spectra showed that the N6-H, the H1″ and H2″ protons reside in the same spin system (Figure 4). Overall, the NMR analysis established that the reaction of dA with 2-deoxyribose provided the desired cross-link remnant 6.

Bottom Line: A synthetic standard was prepared for the putative nucleoside cross-link remnant 6 in which the anomeric carbon of the 2-deoxyribose residue was connected to the exocyclic N(6)-amino group of dA.These findings establish the chemical structure of the dA-Ap cross-link released from duplex DNA and may provide methods for the detection of this lesion in cellular DNA.Both the nucleoside cross-link remnant 6: and the cross-link in duplex DNA were quite stable at pH 7 and 37°C, suggesting that the dA-Ap cross-link could be a persistent lesion with the potential to block the action of various DNA processing enzymes.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Missouri, 125 Chemistry Building, Columbia, MO 65211, USA.

Show MeSH