Neighboring pyrrolidine amide participation in thioether oxidation. methionine as a "hopping" site

Organic Letters

Volumn 13, Issue 11, 2011, Pages 2837-2839

  Glass, Richard S ^a   Schöneich, Christian ^b   Wilson, George S ^b   Nauser, Thomas ^c   Yamamoto, Takuhei ^a   Lorance, Edward ^d   Nichol, Gary S ^a   Ammam, Malika ^b  

^a University of Arizona   (United States)

^b UNIVERSITY OF KANSAS   (United States)

^c LABORATORY OF INORGANIC CHEMISTRY   (Switzerland)

^d Vanguard University of Southern California   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; METHIONINE; PYRROLIDINE; PYRROLIDINE DERIVATIVE; SULFUR;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION;

AMIDES; METHIONINE; MODELS, CHEMICAL; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PYRROLIDINES; SULFUR;

EID: 79957833096     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200793z     Document Type: Article

References (28)

1. Gray, H. B.; Winkler, J. R. Q. Rev. Biophys. 2003, 36, 341-372
2. Cordes, M.; Giese, B. Chem. Soc. Rev. 2009, 38, 892-901
3. Wang, M.; Gao, J.; Müller, P.; Giese, B. Angew. Chem., Int. Ed. 2009, 48, 4232-4234
4. Giese, B.; Wang, M.; Gao, J.; Stoltz, M.; Müller, P.; Graber, M. J. Org. Chem. 2009, 74, 3621-3625
5. Cowan, P. M.; McGavin, S. Nature 1955, 176, 501-503
6. Crick, P. H. C.; Rich, A. Nature 1955, 176, 780-781
7. Steinberg, I. Z.; Harrington, W. F.; Berger, A.; Sela, M.; Katchalski, E. J. Am. Chem. Soc. 1960, 82, 5263-5279
8. Shi, Z.; Chen, K.; Liu, Z.; Kallenbach, N. R. Chem. Rev. 2006, 106, 1877-1897
9. Kuemin, M.; Schweizer, S.; Ochsenfeld, C.; Wennemers, H. J. Am. Chem. Soc. 2009, 131, 15474-15482
10. ·+/MetS) = +1.4 V: Prütz, W. A.; Butler, J.; Land, E. J.; Swallow, A. J. Int. J. Radiat. Biol. 1989, 55, 539-556
11. Brunelle, P.; Schöneich, C.; Rauk, A. Can. J. Chem. 2006, 84, 893-904
12. Glass, R. S.; Petsom, A. M.; Coleman, B. R.; Duchek, J. R.; Klug, J.; Wilson, G. S. J. Am. Chem. Soc. 1988, 110, 4772-4778
13. Glass, R. S.; Hug, G. L.; Schöneich, C.; Wilson, G. S.; Kuznetsova, L.; Lee, T.-M.; Ammam, M.; Lorance, E.; Nauser, T.; Nichol, G. S.; Yamamoto, T. J. Am. Chem. Soc. 2009, 131, 13791-13805
14. -.
15. Mucsi, Z.; Tsai, A.; Szori, M.; Chass, G. A.; Viskolcz, B.; Csizmadia, I. G. J. Phys. Chem. A 2007, 111, 13245-13254
16. von Sonntag, C. The Chemical Basis of Radiation Biology; Taylor & Francis: London, 1987.
17. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209-220
18. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 221-264
19. B3: Becke, A. J. Chem. Phys. 1993, 98, 5648-5652
20. PW91: Burke, K.; Perdew, J. P.; Wang, Y. In Electronic Density Functional Theory: Recent Progress and New Directions; Dobson, J. F.; Vignale, G.; Das, M. P., Eds.; Plenum: New York, 1998.
21. Perdew, J. P. In Electronic Structure of Solids 91; Ziesche, P.; Eschrig, H., Eds.; Verlag: Berlin, 1991; Chapter 11.
22. Perdew, J. P.; Chevary, J. A.; Vosko, S. H.; Jackson, K. A.; Pederson, M. R.; Singh, D. J.; Fiolhais, C. Phys. Rev. B 1992, 46, 6671-6687
23. Perdew, J. P.; Chevary, J. A.; Vosko, S. H.; Jackson, K. A.; Pederson, M. R.; Singh, D. J.; Fiolhais, C. Phys Rev. B 1993, 48, 4978
24. Perdew, J. P.; Burke, K.; Wang, Y. Phys Rev. B 1996, 54, 16533-16539
25. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision D.01; Gaussian, Inc., Wallingford CT, 2004.
26. - couple: Stanbury, D. M. Adv. Inorg. Chem. 1989, 33, 69-138
27. E ° = 2.73 V vs NHE: Wardman, P. J. Phys. Chem. Ref. Data 1989, 18, 1634-1755
28. 2-) = 0.87 V vs NHE. Handbook of Chemistry and Physics, 64 th ed.; CRC Press, Boca Raton, FL, 1984.