View PDF Version
 
DOI: 10.1039/P19940001997 (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1994, 1997-2006

Design and synthesis of transition-state analogues for a cationic cyclisation

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

Ian M. Bell, Chris Abell and Finian J. Leeper

Abstract

Transition-state analogues based upon the 6-(hydroxymethyl)-13-azagona-1,3,5(10),8-tetraene structure (e.g., 40) have been designed and synthesized as part of a programme to elicit antibodies capable of catalysing cationic cyclisations. Methodology for conjugating such analogues to proteins has also been developed.

References

  1. Encyclopedia of Terpenoids, ed. J. S. Glasby, Wiley, Chichester, 1982. Search PubMed.
  2. D. E. Cane, Chem. Rev., 1990, 90, 1089 CrossRef CAS.
  3. For recent reviews see: P. G. Schultz and R. A. Lerner, Acc. Chem. Res., 1993, 26, 391 Search PubMed; J. D. Stewart and S. J. Benkovic, Chem. Soc. Rev., 1993, 14, 213 CrossRef CAS; S. J. Benkovic, Ann. Rev. Biochem., 1992, 61, 29 RSC.
  4. J. Dijkink and W. N. Speckamp, Tetrahedron, 1978, 34, 173 CrossRef CAS.
  5. E. J. Corey and A. Venkateswarlu, J. Am. Chem. Soc., 1972, 94, 6190 CrossRef CAS.
  6. O. Mitsunobu, M. Wada and T. Sano, J. Am, Chem. Soc., 1972, 94, 679 CrossRef.
  7. D. C. Owsley and J. J. Broomfield, Synthesis, 1977, 118 CrossRef CAS.
  8. J. Carlsson, H. Drevin and R. Axen, Biochem. J., 1978, 173, 723 CAS.
  9. F.-T. Liu, M. Zinnecker, T. Hamaoka and D. H. Katz, Biochemistry, 1979, 18, 690 CrossRef CAS.
  10. J. K. Weltman, S. A. Johnson, J. Lanisevin and E. F. Riester, BioTechniques, 1983, 1, 148 Search PubMed.
  11. S. Shaltiel, Biochem. Biophys. Res. Commun., 1967, 29, 178 CAS.
  12. T. W. Greene, Protective Groups in Organic Synthesis, Wiley, New York, 1981. Search PubMed.
  13. J. H. van Boom and C. T. J. Wreesmann, in Oligonucleotide Synthesis, ed. M. J. Gait, IRL Press, Oxford, 1984, pp. 153–183. Search PubMed.
  14. W. C. Still, M. Kahn and A. Mitra, J. Org. Chem., 1978, 43, 2923 CrossRef CAS.
  15. D. D. Perrin, W. L. F. Armarego and D. R. Perrin, Purification of Laboratory Chemicals, 2nd edn., Pergamon Press, Oxford, 1980. Search PubMed.
  16. T. V. RajanBabu, G. S. Reddy and T. Fukunaga, J. Am. Chem. Soc., 1985, 107, 5473 CrossRef CAS.
  17. M. Vincent, J. Maillard and M. Bénard, Bull. Soc. Chim. Fr., 1962, 1580 CAS.
  18. R. S. Goudie and P. N. Preston, J. Chem. Soc. C, 1971, 1718 RSC.
  19. P. J. Lachmann, L. Strangeways, A. Vyakamam and G. Evan, Synthetic Peptides as Antigens (Ciba Foundation Symposium 119), Wiley, Chichester, 1986, pp. 25–27. Search PubMed.
  20. T. Stuchbury, M. Shipton, R. Norris, J. P. G. Malthouse, K. Brocklehurst, J. A. L. Herbert and H. Suschitzky, Biochem. J., 1975, 151, 417 CAS.
Click here to see how this site uses Cookies. View our privacy policy here.