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Wiley-VCH Verlag, ChemInform, 43(34), 2003
Elsevier, Bioorganic and Medicinal Chemistry Letters, 15(13), p. 2445-2447
DOI: 10.1016/s0960-894x(03)00498-0
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Discovery of New Peptide-Based Catalysts for the Direct Asymmetric Aldol Reaction.
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Abstract
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.