View PDF Version
 
DOI: 10.1039/A809266D (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1999, 389-392

The first electrochemical study of epidithiopiperazine-2,5-diones, a special class of α,α′-disulfide bridged cyclic dipeptides

(Note: The full text of this document is currently only available in the PDF Version )

Christina L. L. Chai, Graham A. Heath, Paul B. Huleatt and Gavin A. O’Shea

Abstract

Polarographic stufies of 3,6-epidithiopiperazine-2,5-diones (ETP) including naturally occurring gliotoxin and simple synyhetic analogues are pertinent to understanding their biological action; coulometric measurements on 1,4-diethyl ETP in acetonitrille establish the existance of a ready one-electron reduction overall, in sharp contrast to the familiar two-electron cleavage of acyclic disulfides.

References

  1. A. Taylor, in Microbial Toxins, ed. S. Kadis, A. Ciegler and S. Ajl, Academic Press, New York, 1971, Part VII, p. 337–371 Search PubMed; T. W. Jordan and S. J. Cordiner, Trends Pharmacol. Sci., 1987, 8, 144 Search PubMed; P. G. Sammes, Fortschr. Chem. Org. Naturst., 1975, 32, 51 CrossRef CAS; P. Waring, R. D. Eichner and A. Müllbacher, Med. Res. Rev., 1988, 8, 499 Search PubMed; P. Waring and J. Beaver, Gen. Pharmacol., 1996, 27, 1311 CAS.
  2. P. W. Trown, Biochem. Biophys. Res. Commun., 1968, 33, 402 CAS.
  3. A. M. Hurne, J. Simpson, P. Waring and C. L. L. Chai, Bioorg. Med. Chem. Lett., 1997, 7, 2645 CrossRef CAS.
  4. R. Munday, J. Appl. Toxicol., 1987, 7, 17 CAS.
  5. H. Poisel and U. Schmidt, Angew. Chem., Int. Ed. Engl., 1971, 10, 130 CAS.
  6. B. Kamber, Helv. Chim. Acta, 1971, 54, 927 CAS.
  7. P. Waring, N. Newcombe, M. Edel, Q. H. Lin, H. Jiang, A. Sjaarda, T. Piva and A. Müllbacher, Toxicon., 1994, 32, 491 CrossRef CAS.
  8. B. Breyer and H. H. Bauer, in Chemical Analysis, New York, eds. P. J. Elving and I. M. Kolthoff, Interscience Publishers, 1963, vol. 8 Search PubMed.
  9. B. Nygård, Ark. Kemi, 1967, 28, 75 Search PubMed; B. Nygård, Ark. Kemi, 1967, 28, 89 Search PubMed; B. Nygård and L. Schotte, Acta Chem. Scand., 1956, 10, 469 CAS; J. Ludvík and B. Nygård, J. Electroanal. Chem., 1997, 423, 1 CrossRef CAS.
  10. R. L. Wilson, J. Chem. Soc., Chem. Commun., 1970, 1425 RSC.
  11. K.-D. Asmus, in Methods in Enzymology, Academic Press, New York, eds. L. Packer and A. N. Glazer, 1990, vol. 186, p. 168 Search PubMed; M. Z. Hoffman and E. Hayon, J. Am. Chem. Soc., 1972, 94, 7950 Search PubMed.
  12. See for example M. E. Hall, Anal. Chem., 1953, 25, 556 Search PubMed.
  13. J. Fridrichsons and A. McL. Mathieson, Acta Crystallogr., 1965, 18, 1043 CrossRef CAS; J. Fridrichsons and A. McL. Mathieson, Acta Crystallogr., 1967, 23, 439 CrossRef CAS.
  14. H. Mez, Cryst. Struct. Commun., 1974, 3, 657 Search PubMed.
  15. For early examples, see I. M. Kolthoff and C. Barnum, J. Am. Chem. Soc., 1941, 63, 520 Search PubMed; D. G. Davis and E. Bianco, J. Electroanal. Chem., 1966, 12, 254 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.