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    Proc Natl Acad Sci U S A. 1980 May;77(5):2370-1.

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

    Source

    Max-Planck-Institut for Medical Research, Abteilung Naturstoff-Chemie, Jahnstrasse 29, 6900 Heidelberg, West Germany.

    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.

    PMID:
    16592813
    [PubMed]
    PMCID:
    PMC349399
    Free PMC Article

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