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Studies on cyclic dipeptides, II. Methylated modifications ofcyclo-[Phe-His]

Untersuchungen an cyclischen Dipeptiden, 2. Mitt.: Methylierte Derivate von cyclo-[Phe-His]

  • Organische Cheme Und Biochemie
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Summary

Synthesis of seven new cyclic dipeptides and their conformational analysis based on1HNMR spectra is reported as well as their application as models to elucidate the mechanism of cyclic dipeptide catalysis in enantioselective mandelonitrile formation. Further evidence is presented to support the view that a highly ordered supramolecular complex of dipeptides acts as catalyst.

Zusammenfassung

Es wird die Synthese sieben neuer cyclischer Dipeptide, ihre Konformationsanalyse (basierend auf1H-NMR-Daten) und ihre Anwendung als Modelle zur Aufklärung des Mechanismus der dipeptidkatalysierten enantioselektiven Mandelsäurenitrilsynthese beschrieben. Weitere Hinweise zur Stützung der Annahme, daß ein hoch geordneter supramolekularer Komplex aus Dipeptiden für die Katalyse ausschlaggebend ist, werden vorgelegt.

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Authors and Affiliations

  1. Institut für Pharmazeutische Chemie, Johann-Wolfgang-Goethe-Universität Frankfurt, Christian Doppler Laboratorium für Chemie chiraler Verbindungen, D-60439, Frankfurt/Main, Germany

    C. R. Noe, A. Weigand, S. Pirker & P. Liepert

Authors
  1. C. R. Noe
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  2. A. Weigand
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  3. S. Pirker
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  4. P. Liepert
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Noe, C.R., Weigand, A., Pirker, S. et al. Studies on cyclic dipeptides, II. Methylated modifications ofcyclo-[Phe-His]. Monatsh Chem 128, 301–316 (1997). https://doi.org/10.1007/BF00807896

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  • DOI: https://doi.org/10.1007/BF00807896

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