Communication

A Rationally Designed Aldolase Foldamer†

  1. Manuel M. Müller2,
  2. Matthew A. Windsor1,
  3. William C. Pomerantz Dr.1,
  4. Samuel H. Gellman Prof. Dr.1,
  5. Donald Hilvert Prof. Dr.2

Article first published online: 17 DEC 2008

DOI: 10.1002/anie.200804996

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 48, Issue 5, pages 922–925, January 19, 2009

Additional Information

How to Cite

Müller, Manuel M., Windsor, Matthew A., Pomerantz, William C., Gellman, Samuel H. and Hilvert, D. (2009), A Rationally Designed Aldolase Foldamer. Angew. Chem. Int. Ed., 48: 922–925. doi: 10.1002/anie.200804996

Author Information

  1. 1

    Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706 (USA), Fax: (+1) 608-265-4534

  2. 2

    Laboratorium für Organische Chemie, ETH Zürich, Hönggerberg HCI F339, 8093 Zürich (Switzerland), Fax: (+41) 44-632-1486

  1. †

    This work was supported by the Schweizerischer Nationalfonds, NIH grant GM056414 (to S.H.G.), and the Nanoscale Science and Engineering Center at UW-Madison (NSF DMR-042588). We thank Dr. Dennis Gillingham for help with substrate preparation.

Publication History

  1. Issue published online: 13 JAN 2009
  2. Article first published online: 17 DEC 2008
  3. Manuscript Revised: 11 NOV 2008
  4. Manuscript Received: 13 OCT 2008

Funded by

  • Schweizerischer Nationalfonds
  • NIH. Grant Number: GM056414
  • NSF. Grant Number: DMR-042588

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Keywords:

  • aldol reaction;
  • enzyme models;
  • homogeneous catalysis;
  • peptides;
  • preorganization
Thumbnail image of graphical abstract

Neatly folded: A decameric β-peptide shows enzyme-like catalytic properties. The foldamer, which bears a terminal heptanoyl unit and displays a thermostable helical structure with an array of ammonium-group side chains, accelerates a retroaldol reaction (see scheme) by more than three orders of magnitude through an imine mechanism.

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