Cyclic metallopeptides, cyclo[Gly-L-Cys(terpyPtII)]nCln

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

Kentaro Tanaka, Mitsuhiko Shionoya and Kazuki Shigemori


Abstract

An efficient strategy for the liquid-phase synthesis of cyclic metallopeptides, cyclo[Gly-L-Cys(terpyPtII)]nCln (n = 3, 4), has been developed, which could provide a powerful tool for arraying metal centers on cyclopeptide frameworks.


References

  1. R. Haubner, D. Finsinger and H. Kessler, Angew. Chem., Int. Ed. Engl., 1997, 36, 1374 CrossRef CAS.
  2. W. F. DeGrado, Adv. Protein Chem., 1988, 39, 51 CAS; J. S. Richardson and D. C. Richardson, Trends Biochem. Sci., 1989, 14, 304 CrossRef CAS.
  3. M. R. Ghadiri, J. R. Granja, R. A. Milligan, D. E. McRee and N. Khazanovich, Nature, 1993, 366, 324 CrossRef CAS; M. R. Ghadiri, J. R. Granja and L. Buehler, Nature, 1994, 369, 301 CrossRef CAS; H. S. Kim, J. Hartgerink and M. R. Ghadiri, J. Am. Chem. Soc., 1998, 120, 4417 CrossRef CAS.
  4. For recent examples, see M. R. Ghadiri and C. Choi, J. Am. Chem. Soc., 1990, 112, 1630 Search PubMed; F. Ruan, Y. Chen and J. Hopkins, J. Am. Chem. Soc., 1990, 112, 9403 CrossRef CAS; M. Lieberman and T. Sasaki, J. Am. Chem. Soc., 1991, 113, 2533 CrossRef CAS; C. A. Kim and J. M. Berg, Nature, 1993, 362, 267 CrossRef; D. E. Robertson, R. S. Farid, C. C. Moser, J. L. Urbauer, S. E. Mulholland, R. Pidikiti, J. D. Lear, A. J. Wand, W. F. DeGrado and P. L. Dutton, Nature, 1994, 368, 425 CrossRef CAS; J. Schneider and J. W. Kelly, J. Am. Chem. Soc., 1995, 117, 2533 CrossRef CAS; R. P. Cheng, S. L. Fisher and B. Imperiali, J. Am. Chem. Soc., 1996, 118, 11349 CrossRef CAS; W. D. Kohn, C. M. Kay, B. D. Sykes and R. S. Hodges, J. Am. Chem. Soc., 1998, 120, 1124 CrossRef CAS.
  5. S. J. Lippard, Acc. Chem. Res., 1978, 11, 211 CrossRef CAS.
  6. These metallopeptides were characterized by 1H NMR, ESI MS and elemental analyses.
  7. In the case with n= 2, the intermolecular coupling predominantly occurred to produce the linear octapeptide and then cyclooctapeptide 3 as the main product. The isolation of the desired cyclotetrapeptide as the minor product was not successful.
  8. Comprehensive Supramolecular Chemistry, ed. J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vogtle, J.-M. Lehn and G. W. Gokel, Elsevier Science, Oxford, 1996, vol. 1 Search PubMed.
  9. The binding constants could not be determined accurately due to the low solubility of the complex with carboxylate anions in general solvents.
Click here to see how this site uses Cookies. View our privacy policy here.