Structure of Cyclosporine and Its Metabolites: Total Synthesis of Cyclosporine Metabolites Formed by Oxidation at Positions 4 and 9 of Cyclosporine. Preparation of Leucine-4-cyclosporine, (γ-Hydroxy)-N-methyl-leucine-9-cyclosporine and Leucine-4-(γ-hydroxy)-N-methyl-leucine-9-cyclosporine

Authors

  • Roland M. Wenger
  • Kurt Martin
  • Charles Timbers
  • Anne Tromelin

DOI:

https://doi.org/10.2533/chimia.1992.314

Abstract

The syntheses of the cyclosporine metabolites Leu-4-cyclosporine (AM4N), (γ-OH)MeLeu-9-cyclosporine (AM9) and Leu-4-(γ-OH)MeLeu-cyclosporine (AM4N9) were completed. Aspartic acid was used as starting material to prepare peptides containing (γ-OH)MeLeu residues. The structure of metabolite M13 was definitively established as being Leu-4-(γ-OH)MeLeu-9-cyclosporine. The immunosuppressive activity in vitro of these synthesized metabolites was compared with that of cyclosporine and metabolite AM1.

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Published

1992-08-19

Issue

Vol. 46 No. 7-8 (1992): XIIth International Symposium on Medicinal Chemistry

Section

Forschung

License

Copyright (c) 1992 Swiss Chemical Society

Creative Commons License

This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

How to Cite

[1]
R. M. Wenger, K. Martin, C. Timbers, A. Tromelin, Chimia 1992, 46, 314, DOI: 10.2533/chimia.1992.314.