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An unusual side chain C-C cleavage at the MeBmt amino acid in cyclosporin A

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Summary

The mixture of products obtained by alkaline treatment of cyclosporin A was analyzed by HPLC-continuous-flow-FAB/MS. The changes involve the atypical amino acid (4R)-4-((E)-2-butenyl)-4,N-dimethyl-L-threonine (MeBmt) without affecting the cyclic structure. The main degradation pathway is dehydration producing all four possible anhydro-MeBmt containing cyclosporins. A new cyclosporin, [Sar1]CS, resulting from the side chain cleavage of MeBmt has been isolated and characterized.

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Authors and Affiliations

  1. Galena Co., Research Unit, Branišovská 31, CZ-370 05, České Budějovice, Czech Republic

    A. Jegorov

  2. Institute of Microbiology, Academy of Sciences of the Czech Republic, Prague, Czech Republic

    V. Havlíček & P. Sedmera

Authors
  1. A. Jegorov
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  2. V. Havlíček
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  3. P. Sedmera
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Jegorov, A., Havlíček, V. & Sedmera, P. An unusual side chain C-C cleavage at the MeBmt amino acid in cyclosporin A. Amino Acids 10, 145–151 (1996). https://doi.org/10.1007/BF00806587

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  • DOI: https://doi.org/10.1007/BF00806587

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