Discovery of a highly selective and efficient reagent for formation of intramolecular disulfide bonds in peptides

Journal of the American Chemical Society

Volumn 122, Issue 29, 2000, Pages 6809-6815

  Shi, Tiesheng ^a   Rabenstein, Dallas L ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DISULFIDE; DITHIOL DERIVATIVE; PEPTIDE; PLATINUM COMPLEX; PLATINUM ETHYLENEDIAMINE DICHLORIDE; PRESSINOIC ACID; REAGENT;

ARTICLE; CHEMICAL REACTION KINETICS; DISULFIDE BOND; MOLECULAR DYNAMICS; OXIDATION;

EID: 0034718078     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0008618     Document Type: Article

References (37)

1. For reviews see: (a) Andreu, D.; Albericio, F.; Sole, N. A.; Munson, M. C.; Ferrer, M.; Barany, G. In Peptide Synthesis Protocols; Pennington, M. W., Bunn, B. M., Eds.; Humana Press: Totowa, NJ, 1994; pp 91-169.
2. (b) Moroder, L.; Besse, D.; Musiol, H.-J.; Rudolph-Böhner, S.; Siedler, F. Kopolymers 1996, 40, 207-234.
3. Annis, I.; Hargittai, B.; Barany, G. Methods Enzymol. 1997, 289, 198-221.
4. Tarn, J. P.; Wu, C.-R.; Liu, W.; Zhang, J.-W. J. Am. Chem. Soc. 1991, 113, 6657-6662.
5. Munson, M. C.; Barany, G. J. Am. Chem. Soc. 1993, 115, 10203-10216.
6. Shik, H. J. Org. Chem. 1993, 58, 3003-3008.
7. Annis, I.; Chen, L.; Barany, G. J. Am. Chem. Soc. 1998,120, 7226-7238.
8. Shi, T.; Rabenstein, D. L. J. Org. Chem. 1999, 64, 4590-4595.
9. (a) Fujii, N.; Otaka, A.; Funakoshi, S.; Bessho, K.; Watanabe, T.; Akaji, K.; Yajima, H. Chem. Pharm. Bull. 1987, 35, 2339-2347.
10. (b) Albericio, F.; Hammer, R. P.; Garcia-Echeverria, C.; Molins, M. A.; Chang, J. L.; Munson, M. C.; Pons, M.; Giralt, E.; Barany, G. Int. J. Peptide Protein Res. 1991, 37, 402-413.
11. Goldberg, R. N.; Helper, L. G. Chem. Rev. 1968, 68, 229-252.
12. Shi, T.; Berglund, J.; Elding, L. I. J. Chem. Soc., Dalton Trans. 1997, 2073-2077.
13. Bard, A. J.; Parsons, R.; Jordan, J. Standard Potentials in Aqueous Solution; Marcel Dekker: New York, 1985; pp 345-365.
14. Holmgren, A. Anna. Rev. Biochem. 1985, 54, 237-271.
15. Gan, Z.-R.; Wells, W. W. J. Biol. Chem. 1986, 261, 996-1001.
16. Zapun, A.; Missiakas, D.; Raina, S.; Creighton, T. E. Biochemistry 1995, 34, 5075-5089.
17. (a) Larive, C. K.; Rabenstein, D. L. J. Am. Chem. Soc. 1993,115, 2833-2836.
18. (b) Rabenstein, D. L.; Shi, T.; Spain, S. J. Am. Chem. Soc. 2000, 722, 2401-2402.
19. Shi, T.; Spain, S.; Rabenstein, D. L. Unpublished results.
20. Hope, D. B.; Murti, V. V. S.; Vigneaud, V. D. J. Biol. Chem. 1962, 237, 1563-1566.
21. Hruby, V. J.; Upson, D. A.; Agarwal, N. S. J. Org. Chem. 1977, 42, 3552-3556.
22. Live, D. H.; Agosta, W. C.; Cowburn, D. J. Org. Chem. 1977, 42, 3556-3561.
23. Moore, G. Biochem. J. 1978, 173, 403-409.
24. Lavielle, S.; Chassaing, G.; Ploux, O.; Loeuillet, D.; Besseyre, J.; Julien, S.; Marquet, A.; Convert, O.; Beaujouan, J.-C.; Torrens, Y.; Bergström, L.; Saffroy, M.; Glowinski, J. Biochem. Pharmacol. 1988, 37, 41-49.
25. Lazure, C.; Ong, H.; McNicoll, N.; Netchitailo, P.; Chrétien, M.; De Lean, A.; Vaudry, H. FEBS Lett., 1988, 238, 300-306.
26. Bankowski, K.; Manning, M. J. Med. Chem. 1978, 21, 850-853.
27. Shi, T.; Berglund, J.; Elding, L. I. Inorg. Chem. 1996, .35, 3498-3503.
28. Lemma, K.; Shi, T.; Elding, L. I. Inorg. Chem. 2000, 39, 1728-1734.
29. Shi, T.; Elding, L. I. Inorg. Chim. Ada 1998, 282, 55-60.
30. Wilmarth, W. K.; Fanehiang, Y.-T.; Byrd, J. E. Coord. Chem. Rev. 1983,57, 141-153.
31. Noszal, B.; Guo, W.; Rabenstein, D. L. J. Org. Chem. 1992, 57, 2327-2334.
32. Creighton, T. E. Proteins: Structures and Molecular Properties, 2nd ed.; W. H. Freeman and Company: New York, 1993; Chapter 5.
33. Rabenstein, D. L.; Yeo, P. L. J. Org. Chem. 1994,59,4223-4229.
34. Rabenstein, D. L.; Weaver, K. H. J. Org. Chem. 1996, 61, 7391-7397.
35. Basolo, F.; Bailar, J. C; Tarr, B. P. J. Am. Chem. Soc. 1950, 72, 2433-2438.
36. Poe, A. J. J. Chem. Soc. 1963, 183-188.
37. Yeo, P. L.; Rabenstein, D. L. Anal. Chem. 1993, 65, 3061-3066.