Simplified synthesis of individual stereoisomers of the 4-hydroxynonenal adducts of deoxyguanosine

Tetrahedron Letters

Volumn 54, Issue 32, 2013, Pages 4289-4291

  Christov, Plamen P ^a   Hawkins, Edward K ^a   Kett, Nathan R ^a   Rizzo, Carmelo J ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

4 Hydroxynonenal; Dihydroxylation; DNA adducts; Henry reaction

Indexed keywords

4 HYDROXYNONENAL; 4 NITRO 5 HYDROXY 1 DECENE; ALKENE; AMINE OXIDE; AMINOTRIOL DERIVATIVE; DEOXYGUANOSINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DIHYDROXYLATION; DNA ADDUCT; STEREOISOMERISM; STOICHIOMETRY; SUPERCRITICAL FLUID CHROMATOGRAPHY; SYNTHESIS;

EID: 84879840267     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.06.004     Document Type: Article

References (21)

1. H. Esterbauer Am. J. Clin. Nutr. 57 1993 779S
2. H. Esterbauer, R.J. Schaur, and H. Zollner Free Radical Biol. Med. 11 1991 81
3. C.K. Winter, H.J. Segall, and W.F. Haddon Cancer Res. 46 1986 5682
4. F.L. Chung, R.G. Nath, J. Ocando, A. Nishikawa, and L. Zhang Cancer Res. 60 2000 1507
5. X. Liu, M.A. Lovell, and B.C. Lynn Chem. Res. Toxicol. 19 2006 710
6. H. Wang, and C.J. Rizzo Org. Lett. 3 2001 3603
7. H. Wang, I.D. Kozekov, T.M. Harris, and C.J. Rizzo J. Am. Chem. Soc. 125 2003 5687
8. M.P. Stone, Y.-J. Cho, H. Huang, H.-Y. Kim, I.D. Kozekov, A. Kozekova, H. Wang, I.G. Minko, R.S. Lloyd, T.M. Harris, and C.J. Rizzo Acc. Chem. Res. 41 2008 793
9. H. Huang, I.D. Kozekov, A. Kozekova, H. Wang, R.S. Lloyd, C.J. Rizzo, and M.P. Stone Environ. Mol. Mutagen. 51 2010 625
10. H. Sasai, T. Suzuki, S. Arai, T. Arai, and M. Shibasaki J. Am. Chem. Soc. 114 1992 4418
11. F.A. Luzzio Tetrahedron 57 2001 915
12. J. Boruwa, N. Gogoi, P.P. Saikia, and N.C. Barua Tetrahedron: Asymmetry 17 2006 3315
13. C. Palomo, M. Oiarbide, and A. Laso Eur. J. Org. Chem. 2007 2561
14. G.P. Marsh, P.J. Parsons, C. McCarthy, and X.G. Corniquet Org. Lett. 9 2007 2613
15. R. Ballini, and G. Bosica J. Org. Chem. 62 1997 425
16. D. Mangelings, and Y. Vander Heyden J. Sep. Sci. 31 2008 1252
17. V. VanRheenen, R.C. Kelly, and D.Y. Cha Tetrahedron Lett. 1976 1973
18. A.N. Milas, and S. Sussman J. Am. Chem. Soc. 58 1936 1302
19. T.J. Donohoe, K.M.P. Wheelhouse, P.J. Lindsay-Scott, P.A. Glossop, I.A. Nash, and J.S. Parker Angew. Chem., Int. Ed. 47 2008 2872
20. M. Zelikoff, and H.A. Taylor J. Am. Chem. Soc. 72 1950 5039
21. K.B. Sharpless, and K. Akashi J. Am. Chem. Soc. 98 1976 1986