2,3-trans-3,4-trans-3,4-Dihydroxy-L-proline: An amino acid in toxic peptides of 
Amanita virosa mushrooms

Buku, Angeliki; Faulstich, Heinz; Wieland, Theodor; Dabrowski, Janusz

doi:10.1073/pnas.77.5.2370

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2,3-trans-3,4-trans-3,4-Dihydroxy-L-proline: An amino acid in toxic peptides of Amanita virosa mushrooms

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Buku, Angeliki
Max Planck Institute for Medical Research, Max Planck Society;

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Faulstich, Heinz
Department of Molecular Cell Research, Max Planck Institute for Medical Research, Max Planck Society;

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Wieland, Theodor
Max Planck Institute for Medical Research, Max Planck Society;

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Dabrowski, Janusz
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Citation

Buku, A., Faulstich, H., Wieland, T., & Dabrowski, J. (1980). 2,3-trans-3,4-trans-3,4-Dihydroxy-L-proline: An amino acid in toxic peptides of Amanita virosa mushrooms. Proceedings of the National Academy of Sciences of the United States of America, 77(5), 2370-2371. doi:10.1073/pnas.77.5.2370.

Cite as: https://hdl.handle.net/21.11116/0000-0004-862F-1

Abstract

Among the four possible stereoisomers of 3,4-dihydroxy-L-proline,2,3-trans-3,4-trans-3,4-dihydroxy-L-proline (IV) had not been found in nature previously. It has now been detected as a component of virotoxins, toxic peptides of Amanita virosa mushrooms. Because periodate failed to effect an oxidative glycol splitting reaction, the two hydroxyl groups in positions 3 and 4 were expected to be in a trans configuration. Furthermore, the formation of a 4-lactone on treatment with acids pointed to the carboxyl group and the hydroxyl group at position 4 being in a cis configuration. These results are in agreement with structure IV only. Final proof for structure IV was given by NMR spectroscopy and direct comparison with the 2,3-cis-3,4-trans-3,4-dihydroxy-L-proline isomer.