Molecule of the Month
November 2006
A Model Aldolase Peptide Dendrimer

Peptide dendrimers are attractive as models for enzymes because they are easily prepared by solid phase peptide synthesis and given their globular shape omit the difficult problem of protein folding.
The model aldolase peptide dendrimer shown here displays multiple catalytic sites in the form of Pro-Lys dyads (red-cyan) and features a hydrophobic core (blue) for substrate binding. Like an aldolase enzyme it catalyzes the condensation of aldehydes and ketones under both organic and aqueous conditions using 1 mole% catalyst and gives access to the aldol product in good yield and up to 65% e.e.

This work was carried out in the group of Prof. Jean-Louis Reymond.

References:

  • J. Kofoed, T. Darbre, J.-L. Reymond;
    "Artificial aldolases from peptide dendrimer combinatorial libraries"
    Org. Biomol. Chem., 4, 3268-3281, (2006); doi:10.1039/B607342E.