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Spectroscopic characterization of interstrand carbinolamine cross-links formed in the 5'-CpG-3' sequence by the acrolein-derived gamma-OH-1,N2-propano-2'-deoxyguanosine DNA adduct.
Cho YJ, Kim HY, Huang H, Slutsky A, Minko IG, Wang H, Nechev LV, Kozekov ID, Kozekova A, Tamura P, Jacob J, Voehler M, Harris TM, Lloyd RS, Rizzo CJ, Stone MP. Cho YJ, et al. Among authors: huang h. J Am Chem Soc. 2005 Dec 21;127(50):17686-96. doi: 10.1021/ja053897e. J Am Chem Soc. 2005. PMID: 16351098 Free PMC article.
The stereochemistry of trans-4-hydroxynonenal-derived exocyclic 1,N2-2'-deoxyguanosine adducts modulates formation of interstrand cross-links in the 5'-CpG-3' sequence.
Huang H, Wang H, Qi N, Lloyd RS, Rizzo CJ, Stone MP. Huang H, et al. Biochemistry. 2008 Nov 4;47(44):11457-72. doi: 10.1021/bi8011143. Epub 2008 Oct 11. Biochemistry. 2008. PMID: 18847226 Free PMC article.
Both exist primarily as diastereomeric cyclic hemiacetals when placed into duplex DNA [Huang, H., Wang, H., Qi, N., Kozekova, A., Rizzo, C. J., and Stone, M. P. (2008) J. Am. ...
Both exist primarily as diastereomeric cyclic hemiacetals when placed into duplex DNA [Huang, H., Wang, H., Qi, N., Koz …
Conformational interconversion of the trans-4-hydroxynonenal-derived (6S,8R,11S) 1,N(2)-deoxyguanosine adduct when mismatched with deoxyadenosine in DNA.
Huang H, Wang H, Lloyd RS, Rizzo CJ, Stone MP. Huang H, et al. Chem Res Toxicol. 2009 Jan;22(1):187-200. doi: 10.1021/tx800320m. Chem Res Toxicol. 2009. PMID: 19053179 Free PMC article.
This was in contrast to when this adduct was correctly paired with dCyd, conditions under which it underwent ring opening and rearrangement to diastereomeric minor groove cyclic hemiacetals [ Huang , H. , Wang , H. , Qi , N. , Lloyd , R. S. , Harris , T. M. , …
This was in contrast to when this adduct was correctly paired with dCyd, conditions under which it underwent ring opening and rearrangement …
DNA cross-link induced by trans-4-hydroxynonenal.
Huang H, Kozekov ID, Kozekova A, Wang H, Lloyd RS, Rizzo CJ, Stone MP. Huang H, et al. Environ Mol Mutagen. 2010 Jul;51(6):625-34. doi: 10.1002/em.20599. Environ Mol Mutagen. 2010. PMID: 20577992 Free PMC article. Review.
γ-Hydroxy-1,N2-propano-2'-deoxyguanosine DNA adduct conjugates the N-terminal amine of the KWKK peptide via a carbinolamine linkage.
Huang H, Wang H, Voehler MW, Kozekova A, Rizzo CJ, McCullough AK, Lloyd RS, Stone MP. Huang H, et al. Chem Res Toxicol. 2011 Jul 18;24(7):1123-33. doi: 10.1021/tx200113n. Epub 2011 May 11. Chem Res Toxicol. 2011. PMID: 21561113 Free PMC article.
The structures of the diastereomeric DNA-KWKK conjugates were predicted from potential energy minimization of model structures derived from the refined structure of the fully reduced cross-link [ Huang, H., Kozekov, I. D., Kozekova, A., Rizzo, C. J., McCullough, A., …
The structures of the diastereomeric DNA-KWKK conjugates were predicted from potential energy minimization of model structures derived from …
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