Communication

Siamese Depsipeptides: Constrained Bicyclic Architectures†

  1. Javier Ruiz-Rodríguez Dr.1,
  2. Jan Spengler Dr.1,2,
  3. Fernando Albericio Prof.1,2,3

Article first published online: 6 OCT 2009

DOI: 10.1002/anie.200904135

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 48, Issue 45, pages 8564–8567, October 26, 2009

Additional Information

How to Cite

Ruiz-Rodríguez, J., Spengler, J. and Albericio, F. (2009), Siamese Depsipeptides: Constrained Bicyclic Architectures. Angew. Chem. Int. Ed., 48: 8564–8567. doi: 10.1002/anie.200904135

Author Information

  1. 1

    Institute for Research in Biomedicine, Barcelona Science Park (PCB), Baldiri Reixac 10, 08028-Barcelona (Spain), Fax: (+34) 93-403-7126 http://www.pcb.ub.es/fama/

  2. 2

    CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, PCB, Baldiri Reixac 10, 08028-Barcelona (Spain)

  3. 3

    Department of Organic Chemistry, University of Barcelona, Martí i Franqués 1–11, 08028-Barcelona (Spain)

  1. †

    We kindly acknowledge Dr. Miguel Moreno (PCB) and Andres M. Francesc from PharmaMar, S.A.U., 28770-Colmenar Viejo, Madrid (Spain) for the performance of the cell assays. We thank the Barcelona Science Park for the facilities (Confocal Laboratory, and Nuclear Magnetic Resonance Laboratory). This study was supported by CICYT (CTQ2006-03794/BQU, CTQ2008-00177), the Generalitat de Catalunya (2005SGR 00662), the Barcelona Science Park, and the Institute for Research in Biomedicine.

Publication History

  1. Issue published online: 20 OCT 2009
  2. Article first published online: 6 OCT 2009
  3. Manuscript Revised: 3 SEP 2009
  4. Manuscript Received: 26 JUL 2009

Funded by

  • CICYT. Grant Numbers: CTQ2006-03794/BQU, CTQ2008-00177
  • Generalitat de Catalunya. Grant Number: 2005SGR 00662
  • Barcelona Science Park
  • Institute for Research in Biomedicine

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Keywords:

  • biological activity;
  • bioorganic chemistry;
  • depsipeptides;
  • structure–activity relationships;
  • tartaric acid
Thumbnail image of graphical abstract

The first members of a new class of depsipeptides with tartaric acid as the core unit, called Siamese depsipeptides, are described. These compounds were synthesized from a branched precursor in only one cyclization step. The structural manipulation of a natural bioactive depsipeptide (sansalvamide A) gives analogues with greater activity, and thereby provides additional information on structure–activity relationships (see structures).

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