(+)-Zwittermicin A: Assignment of its Complete Configuration by Total Synthesis of the Enantiomer and Implication of D-Serine in its Biosynthesis

Authors

  • Evan W. Rogers,

    1. Department of Chemistry and Biochemistry and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA, 92093-0358 (USA), Fax: (+1) 858-822-0386
    Search for more papers by this author
  • Doralyn S. Dalisay,

    1. Department of Chemistry and Biochemistry and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA, 92093-0358 (USA), Fax: (+1) 858-822-0386
    Search for more papers by this author
  • Tadeusz F. Molinski Prof. Dr.

    1. Department of Chemistry and Biochemistry and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA, 92093-0358 (USA), Fax: (+1) 858-822-0386
    Search for more papers by this author

  • Financial support for this work was provided by the National Institutes of Health (RO1 AI039987). We are grateful to Prof. T. M. Zabriskie (Oregon State University) and Prof. M. Burkart (UC San Diego) for helpful discussions. HRMS measurements were carried out by R. New (UC Riverside) and Y. X. Su (UC San Diego). We thank D. Manker (Novo Nordisk, Entotech Inc, Davis, CA) for a gift of authentic (+)-1.

Abstract

original image

D-Serin ist der Hauptverdächtige: Die Totalsynthese von (−)-Zwittermicin A gelang ausgehend von einer geschützten C2-symmetrischen Diaminotetraol-Einheit und ermöglichte die vollständige stereochemische Zuordnung von natürlichem (+)-Zwittermicin A. Die unerwartete 14R-Konfiguration legt die Beteiligung eines „D-Serin“-Motivs an der Biosynthese von (+)-Zwittermicin A nahe.

Ancillary