Skip to main content
SpringerLink
Log in

Semi-synthesis of A23187 (calcimycin) analogs

  • Short Communications
  • Published:
Experientia Aims and scope Submit manuscript

Summary

The cleavage of A23187 to give a synthon (4) and the semi-synthesis from (4) of 2 Des-N-methylamino A23187 isomers (7a,b) are described. The antibiotic activities of the acids analogous to A23187(1), (2), (7a), (7b) are compared.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

References

  1. Hamill, R.L., Gorman, M., Gale, R.M., Higgens, C.E. and Hoehm, N.M., 12th Interscience Conference on Antimicrobial Agents and Chemotherapy, Atlantic City (N.J.) 1972, abstr. p. 32.

  2. Tissier, C., Juillard, J., Dupin, M., and Jeminet, G., J. Chim. phys.76 (1979) 611.

    Article  CAS  Google Scholar 

  3. Reed, P.W., and Lardy, H.A., J. biol. Chem.247 (1972) 6970.

    Article  CAS  PubMed  Google Scholar 

  4. Pfeiffer, D.R., Taylor, R.W., and Lardy, H.A., Annl. N.Y. Acad. Sci.307, (1978) 402.

    Article  CAS  Google Scholar 

  5. Baker, E.P., in: Antibiotics. Ed. F.E. Hahn, Springer, Berlin 1979.

    Google Scholar 

  6. Chaney, M.O., Jones, N.D., and Debono, M., J. Antibiot.29 (1976) 424.

    Article  CAS  Google Scholar 

  7. Alleaume, M., Barrans, Y., and Jeminet, G., submitted.

  8. For confirmation of structure, we compared totally assigned1H (Anteunis, M.J.O., Bioorg. Chem.6 (1977) 1) and13C (David, L., Guittet, E., Lallemand, J.Y., and Beloeil, J.C., Nouv. J. Chim.5 (1981) 531) NMR-spectra of calcimycin with compounds2–7. Only characteristic peaks are given in this communication. For all the compounds, we used the unmodified numbering of calcimycin skeleton.

  9. Shiozaki, M., Ishida, N., Iono, K., and Hiraoka, T., Tetrahedron36 (1980) 2736.

    Article  Google Scholar 

  10. All the reactions were protected from light. The crude products were purified by TLC (silica gel, eluting with several solvents: cyclohexane-ethylacetate 50–50 (4,5b) cyclohexane-ethylacetate 70–30 (5a,6b) ether (6a), ethylacetate (7a,7b). All the analysis conform to the proposed formula.

  11. Benzotriazol-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorphosphat.

  12. Castro, B., Dormoy, J.R., Dourtoglou, B., Evin, G., Selve, C. and Ziegler, J.C., Synthesis (Communication) (1976) 751.

  13. Kanaoka, Y., Hamada, T., and Yonemitsu, O., Chem. Pharm. Bull.18 (1970) 587.

    Article  CAS  Google Scholar 

  14. David, L. and Kergomard, A., J. Antibiotics35 (1982) 1409.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Laboratoire de Chimie Organique Biologique (E.R.A. 392 du CNRS), Université de Clermont-Ferrand II, 24, Avenue des Landais, F-63170, Aubiere, France

    M. Prudhomme & G. Jeminet

Authors
  1. M. Prudhomme
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. Jeminet
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Acknowledgment. The authors are very grateful to Drs G. Dauphin and J.Y. Lallemand for the NMR-spectra at 400 MHz performed in Gif-sur-Yvette, To Dr J.G. Gourcy and Mrs G. Kergomard for technical assistance.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Prudhomme, M., Jeminet, G. Semi-synthesis of A23187 (calcimycin) analogs. Experientia 39, 256–258 (1983). https://doi.org/10.1007/BF01955290

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01955290

Keywords

Search

Navigation