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
DOI:
https://doi.org/10.2533/chimia.1992.314Abstract
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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1992-08-19
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Copyright (c) 1992 Swiss Chemical Society
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[1]
R. M. Wenger, K. Martin, C. Timbers, A. Tromelin, Chimia 1992, 46, 314, DOI: 10.2533/chimia.1992.314.