Transformation of thiols to disulfides by epolactaene and its derivatives

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 14, 2011, Pages 4162-4172

  Kuramochi, Kouji ^a   Sunoki, Takashi ^b   Tsubaki, Kazunori ^a   Mizushina, Yoshiyuki ^c   Sakaguchi, Kengo ^b   Sugawara, Fumio ^b   Ikekita, Masahiko ^b   Kobayashi, Susumu ^b  

^a KYOTO PREFECTURAL UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

^c KOBE GAKUIN UNIVERSITY   (Japan)

Author keywords

Lactam; Disulfide; Epolactaene; Epoxide; Thiol; Thiolysis

Indexed keywords

1 BENZOYL 4 HYDROXY 4 METHYL 6 OXA 3 AZABICYCLO[3.1.0]HEXAN 2 ONE; 3 DODECANOYL 5 HYDROXY 5 METHYL 3 PYRROLIN 2 ONE; 3 OXO 2 PHENYLSULFANYLTETRADECANAMIDE; 3 OXOTETRADECANAMIDE; 4 HYDROXY 5 METHOXY 5 METHYL 3 PHENYLSULFANYL 2 PYRROLIDINONE; 4 HYDROXY 5 METHYL 3,5 BIS(PHENYLSULFANYL) 2 PYRROLIDINONE; 4,5 DIHYDROXY 5 METHYL 3 PHENYLSULFANYL 2 PYRROLIDINONE;; 5 HYDROXY 5 METHYL 3 PHENYLSULFANYL 3 PYRROLIN 2 ONE; ACETYLCYSTEINE DERIVATIVE; ALPHA LACTAM; BICARBONATE; CHEMICAL COMPOUND; DISULFIDE; EPOLACTAENE DERIVATIVE; LACTAM; N ACETYL[1 (AMINOCARBONYL) 2 OXOOCTANYL]CYSTEINATE; PHOSPHATE BUFFERED SALINE; REAGENT; THIOL DERIVATIVE; THIOPHENOL; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; BIOTRANSFORMATION; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CLAIZEN REACTION; DISULFIDE BOND; PH; ROOM TEMPERATURE; SOLVENT EFFECT; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

DISULFIDES; EPOXY COMPOUNDS; MOLECULAR STRUCTURE; POLYENES; STEREOISOMERISM; SULFHYDRYL COMPOUNDS;

EID: 79960015648     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.06.015     Document Type: Article

References (41)

1. W.J. Lees Curr. Opin. Chem. Biol. 12 2008 740
2. C.S. Sevier, and C.A. Kaiser Antioxid. Redox Signal. 8 2006 797
3. G. Bulaj Biotechnol. Adv. 23 2005 87
4. H. Ishikawa, S. Kim, K. Kwak, K. Wakasugi, and M.D. Fayer Proc. Natl. Acad. Sci. U.S.A. 104 2007 19309
5. K. Piotukh, D. Kosslick, J. Zimmermann, E. Krause, and C. Freund Free Radical Biol. Med. 43 2007 1263
6. C. Lee, S.M. Lee, P. Mukhopadhyay, S.J. Kim, S.C. Lee, W.S. Ahn, M.H. Yu, G. Storz, and S.E. Ryu Nat. Struct. Mol. Biol. 11 2004 1179
7. J. Riemer, N. Bulleid, and J.M. Herrmann Science 324 2009 1284
8. A. Rietsch, and J. Beckwith Annu. Rev. Genet. 32 1998 163
9. J. Messens, and J.F. Collet Int. J. Biochem. Cell Biol. 38 2006 1050
10. R.C. Cumming, N.L. Andon, P.A. Haynes, M. Park, W.H. Fischer, and D. Schubert J. Biol. Chem. 279 2004 21749
11. H. Kakeya, I. Takahashi, G. Okada, K. Isono, and H. Osada J. Antibiot. 48 1995 733
12. H. Kakeya, C. Onozawa, M. Sato, K. Arai, and H. Osada J. Med. Chem. 40 1997 391
13. Y. Nagumo, H. Kakeya, M. Shoji, Y. Hayashi, M. Dohmae, and H. Osada Biochem. J. 387 2005 835
14. Y. Nagumo, H. Kakeya, J. Yamaguchi, T. Uno, M. Shoji, Y. Hayashi, and H. Osada Bioorg. Med. Chem. Lett. 14 2004 4425
15. J. Nakai, K. Kawada, S. Nagata, K. Kuramochi, H. Uchiro, S. Kobayashi, and M. Ikekita Biochim. Biophys. Acta 1581 2002 1
16. K. Kuramochi, R. Matsui, Y. Matsubara, J. Nakai, T. Sunoki, S. Arai, S. Nagata, Y. Nagahara, Y. Mizushina, M. Ikekita, and S. Kobayashi Bioorg. Med. Chem. 14 2006 2151
17. Y. Mizushina, S. Kobayashi, K. Kuramochi, S. Nagata, F. Sugawara, and K. Sakaguchi Biochem. Biophys. Res. Commun. 273 2000 784
18. K. Kuramochi, Y. Mizushina, S. Nagata, F. Sugawara, K. Sakaguchi, and S. Kobayashi Bioorg. Med. Chem. 12 2004 1983
19. Y. Mizushina, K. Kuramochi, H. Ikawa, I. Kuriyama, N. Shimazaki, M. Takemura, M. Oshige, H. Yoshida, O. Koiwai, F. Sugawara, S. Kobayashi, and K. Sakaguchi Int. J. Mol. Med. 15 2005 785
20. K. Kuramochi, H. Itaya, S. Nagata, K. Takao, and S. Kobayashi Tetrahedron Lett. 40 1999 7367
21. K. Kuramochi, S. Nagata, H. Itaya, K. Takao, and S. Kobayashi Tetrahedron Lett. 40 1999 7371
22. K. Kuramochi, S. Nagata, H. Itaya, Y. Matsubara, T. Sunoki, H. Uchiro, K. Takao, and S. Kobayashi Tetrahedron 59 2003 9743
23. Total synthesis of epolactaene: Y. Hayashi, and K. Narasaka Chem. Lett. 1998 313
24. Y. Hayashi, J. Kanayama, J. Yamaguchi, and M. Shoji J. Org. Chem. 67 2002 9443
25. S. Marumoto, H. Kogen, and S. Naruto J. Org. Chem. 63 1998 2068
26. S. Marumoto, H. Kogen, and S. Naruto Tetrahedron 55 1999 7129
27. S. Marumoto, H. Kogen, and S. Naruto Tetrahedron 55 1999 7145
28. Z. Tan, and E. Negishi Org. Lett. 8 2006 2783
29. K. Kuramochi, S. Yukizawa, S. Ikeda, T. Sunoki, S. Arai, R. Matsui, A. Morita, Y. Mizushina, K. Sakaguchi, F. Sugawara, M. Ikekita, and S. Kobayashi Bioorg. Med. Chem. 16 2008 5039
30. J.M. Sayer, P. Conlon, J. Hupp, J. Fancher, R. Belanger, and E.J. White J. Am. Chem. Soc. 101 1979 1890
31. E.L. Loechler, and T.C. Hollocher J. Am. Chem. Soc. 102 1980 7312
32. D.A. Forsyth, and J.A. Hanley J. Am. Chem. Soc. 109 1987 7930
33. S. Sato, R. Sakai, and M. Kodama Bioorg. Med. Chem. Lett. 10 2000 1787
34. S. Sakamoto, S. Sato, T. Ogata, and M. Kodama Fish. Sci. 66 2000 136
35. J. Wu, and H.G. Xia Green Chem. 7 2005 708
36. C. Mukherjee, G.H. Maiti, and A.K. Misra ARKIVOC 2008 46
37. P. Magnus, T. Katoh, I.R. Matthew, and J.C. Huffman J. Am. Chem. Soc. 111 1989 6707
38. J. Durman, J. Elliott, A.B. McElroy, and S. Warren J. Chem. Soc., Perkin Trans. 1 1985 1237
39. N.N. Girotra, and N.L. Wendler Tetrahedron Lett. 20 1979 4793
40. H. Funabashi, S. Iwasaki, S. Okuda, and S. Õmura Tetrahedron Lett. 24 1983 2673
41. H. Funabashi, A. Kawaguchi, H. Tomoda, S. Õmura, S. Okuda, and S. Iwasaki J. Biochem. (Tokyo) 105 1989 751