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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

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.

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PNAS_77_1980_2370.pdf (beliebiger Volltext), 398KB
 
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https://www.pnas.org/content/pnas/77/5/2370.full.pdf (beliebiger Volltext)
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 Urheber:
Buku, Angeliki1, Autor           
Faulstich, Heinz2, Autor           
Wieland, Theodor1, Autor           
Dabrowski, Janusz3, Autor           
Affiliations:
1Max Planck Institute for Medical Research, Max Planck Society, ou_1125545              
2Department of Molecular Cell Research, Max Planck Institute for Medical Research, Max Planck Society, ou_1497703              
3Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society, ou_1497706              

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Schlagwörter: mushroom toxins; virotoxins; dihydroxyproline
 Zusammenfassung: 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.

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Sprache(n): eng - English
 Datum: 1980-05-01
 Publikationsstatus: Erschienen
 Seiten: 2
 Ort, Verlag, Ausgabe: -
 Inhaltsverzeichnis: -
 Art der Begutachtung: Expertenbegutachtung
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Titel: Proceedings of the National Academy of Sciences of the United States of America
  Andere : Proc. Acad. Sci. USA
  Andere : Proc. Acad. Sci. U.S.A.
  Andere : Proceedings of the National Academy of Sciences of the USA
  Kurztitel : PNAS
Genre der Quelle: Zeitschrift
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Ort, Verlag, Ausgabe: Washington, D.C. : National Academy of Sciences
Seiten: - Band / Heft: 77 (5) Artikelnummer: - Start- / Endseite: 2370 - 2371 Identifikator: ISSN: 0027-8424
CoNE: https://pure.mpg.de/cone/journals/resource/954925427230