Discovery of new peptide-based catalysts for the direct asymmetric aldol reaction.
A series of oligo-peptide based catalysts were prepared using Fmoc solid-phase peptide synthesis. It was found that peptides with N-terminal proline residues catalyzed an aldol reaction yielding enantiomeric enriched product. Peptide H-Pro-Glu-Leu-Phe-OH catalyzed the reaction with good activity and moderate enantioselectivity (66% ee). Furthermore, it was shown that an acidic side chain and/or C-termini are essential to catalysis.
Kofoed
Jacob
J
Department of Chemistry and Biochemistry, University of Berne, Freiestrasse 3, 3012 Bern, Switzerland.
Nielsen
John
J
Reymond
Jean-Louis
JL
D000096:Acetone; D000477:Alkylating Agents; D001547:Benzaldehydes; D002384:Catalysis; D005634:Fructose-Bisphosphate Aldolase / Q000737:chemistry / Q000378:metabolism; D007202:Indicators and Reagents; D009842:Oligopeptides / Q000737:chemistry*; D011392:Proline / Q000737:chemistry
D000477:Alkylating Agents; D001547:Benzaldehydes; D007202:Indicators and Reagents; D009842:Oligopeptides; D000096:Acetone; C029915:4-nitrobenzaldehyde; D011392:Proline; D005634:Fructose-Bisphosphate Aldolase