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5(4H)-Oxazolones as Intermediates in the Carbodiimide- and Cyanamide-Promoted Peptide Activations in Aqueous Solution†

  1. Dr. Grégoire Danger1,*,
  2. Arthur Michaut1,2,
  3. Manon Bucchi2,
  4. Dr. Laurent Boiteau2,
  5. Justine Canal2,
  6. Dr. Raphaël Plasson3,
  7. Dr. Robert Pascal2,*

Article first published online: 21 NOV 2012

DOI: 10.1002/ange.201207730

Issue

Angewandte Chemie

Angewandte Chemie

Volume 125, Issue 2, pages 639–642, January 7, 2013

Additional Information

How to Cite

Danger, G., Michaut, A., Bucchi, M., Boiteau, L., Canal, J., Plasson, R. and Pascal, R. (2013), 5(4H)-Oxazolones as Intermediates in the Carbodiimide- and Cyanamide-Promoted Peptide Activations in Aqueous Solution . Angew. Chem., 125: 639–642. doi: 10.1002/ange.201207730

Author Information

  1. 1

    Spectrométries et Dynamique Moléculaire, Physique des Interactions Ioniques et Moléculaires, UMR 7345, CNRS—Aix-Marseille Université, Centre Saint-Jérôme—case 252, 13397 Marseille, Cedex 20 (France)

  2. 2

    Institut des Biomolécules Max Mousseron, UMR 5247, CNRS—Université Montpellier 1 & Montpellier 2, CC17006, Place E. Bataillon, 34095 Montpellier (France)

  3. 3

    Department of Earth and Planetary Sciences, Harvard University, 100 Edwin H. Lane Bvd, Cambridge, MA 02142 (USA)

*Spectrométries et Dynamique Moléculaire, Physique des Interactions Ioniques et Moléculaires, UMR 7345, CNRS—Aix-Marseille Université, Centre Saint-Jérôme—case 252, 13397 Marseille, Cedex 20 (France)

  1. †

    We are indebted to the interdisciplinary program of the CNRS Planetary Environments and Origins of Life (EPOV) for support, and to the COST Action CM0703 “Systems chemistry” for providing the possibility of fruitful scientific exchanges during the realization of this work.

Publication History

  1. Issue published online: 28 DEC 2012
  2. Article first published online: 21 NOV 2012
  3. Manuscript Revised: 18 OCT 2012
  4. Manuscript Received: 25 SEP 2012

Funded by

  • CNRS
  • COST Action

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Keywords:

  • Aminosäuren;
  • Chiralität;
  • NMR-Spektroskopie;
  • Peptide;
  • Reaktive Zwischenstufen
Thumbnail image of graphical abstract

Wie in der guten alten Zeit? Die Bildung von 5(4H)-Oxazolonen wird in der Peptidchemie üblicherweise vermieden. Ergebnisse zeigen nun aber, dass 5(4H)-Oxazolone als Zwischenstufen bei der Peptidbildung durch Cyanamid- und Carbodiimid-Aktivierung in wässriger Lösung auftreten (siehe Schema).

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