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Total Synthesis and Structural Revision of the Antibiotic Tetrapeptide GE81112A |
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| Authors: | Dr. Gerrit Jürjens Dr. Sören M. M. Schuler Dr. Michael Kurz Dr. Sylvain Petit Dr. Cédric Couturier Dr. Frédéric Jeannot Fabian Nguyen Dr. Raffael C. Wende Prof. Dr. Peter E. Hammann Prof. Dr. Daniel N. Wilson Dr. Eric Bacqué Dr. Christoph Pöverlein Dr. Armin Bauer |
| Affiliation: | 1. Fraunhofer IME, Projektgruppe Bioressourcen, Gie?en, Germany;2. Helmholtz Zentrum München, Institut für Medizinalchemie, Hannover, Germany;3. R&D Integrated Drug Discovery, Sanofi-Aventis Deutschland GmbH, Frankfurt am Main, Germany;4. Therapeutic Area Infectious Diseases, Sanofi R&D, Marcy L'Etoile, France;5. Present address: UCB Pharma SA, Braine-L'Alleud, Belgium;6. Gene Center, Department for Biochemistry and Center for Protein Science Munich (CiPSM), Ludwig-Maximilians-Universit?t, München, Germany;7. Present address: Institut für Biochemie und Molekularbiologie, Universit?t Hamburg, Germany;8. R&D Therapeutic Area Infectious Diseases, Sanofi-Aventis Deutschland GmbH, Frankfurt am Main, Germany |
| Abstract: | The total synthesis of the naturally occurring antibiotic GE81112A, a densely functionalized tetrapeptide, is reported. Comparison of spectral data with those of the natural product and the lack of biological activity of the synthesized compound led us to revise the published configuration of the 3‐hydroxypipecolic acid moiety. This hypothesis was fully validated by the synthesis of the corresponding epimer. |
| Keywords: | antibiotics non-ribosomal peptide synthesis peptides structural revision total synthesis |