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Increased Structural Complexity Leads to Higher Activity: Peptides as Efficient and Versatile Catalysts for Asymmetric Aldol Reactions
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Section:Abstract
Peptides containing a secondary amine and a carboxylic acid in a specific orientation to each other are presented as highly efficient catalysts for asymmetric aldol reactions: (1) their activity is considerably higher compared to that of proline, and (2) the enantioselectivity of the peptidic catalysts can be changed from (R)- to (S)-selectivity by simple modifications of the secondary structure.
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This article has been cited by 21 ACS Journal articles (5 most recent appear below).
N-Prolinylanthranilamide Pseudopeptides as Bifunctional Organocatalysts for Asymmetric Aldol Reactions
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Anthony J. Pearson and Santanu PandaOrganic Letters2011 13 (20), 5548-5551Proline anthranilamide-based pseudopeptides were shown to be effective organocatalysts for enantioselective direct aldol reactions of a selection of aldehydes with various ketones with excellent yield, enantioselectivity up to 99% and anti to syn ...
Combinatorial Discovery of Peptide Dendrimer Enzyme Models Hydrolyzing Isobutyryl Fluorescein
Noélie Maillard, Rasomoy Biswas, Tamis Darbre, and Jean-Louis ReymondACS Combinatorial Science2011 13 (3), 310-320Combinatorial Discovery of Peptide Dendrimer Enzyme Models Hydrolyzing Isobutyryl Fluorescein
Noélie Maillard, Rasomoy Biswas, Tamis Darbre, and Jean-Louis ReymondACS Combinatorial Science2011 13 (3), 310-320Two 6750-membered one-bead-one-compound peptide dendrimer combinatorial libraries L (X4)8(LysX3)4(LysX2)2LysX1 (X1−4 = 14 different amino acids or deletion, Lys = branching lysine residue) and AcL (with N-terminal acetylation) were prepared by split-and-...
Asymmetric Aldol Reaction Organocatalyzed by (S)-Proline-Containing Dipeptides: Improved Stereoinduction under Solvent-Free Conditions
José G. Hernández and Eusebio JuaristiThe Journal of Organic Chemistry2011 76 (5), 1464-1467Asymmetric Aldol Reaction Organocatalyzed by (S)-Proline-Containing Dipeptides: Improved Stereoinduction under Solvent-Free Conditions
José G. Hernández and Eusebio JuaristiThe Journal of Organic Chemistry2011 76 (5), 1464-1467The organocatalytic activity of the methyl ester of (S)-proline-(S)-phenylalanine, (S,S)-2, in the asymmetric aldol reaction between cyclohexanone and acetone with various aromatic aldehydes under solvent-free conditions in a ball mill has been evaluated. ...
Efficient Asymmetric α-Oxyamination of Aldehydes by Resin-Supported Peptide Catalyst in Aqueous Media
Kengo Akagawa, Takuma Fujiwara, Seiji Sakamoto and Kazuaki KudoOrganic Letters2010 12 (8), 1804-1807Efficient Asymmetric α-Oxyamination of Aldehydes by Resin-Supported Peptide Catalyst in Aqueous Media
Kengo Akagawa, Takuma Fujiwara, Seiji Sakamoto and Kazuaki KudoOrganic Letters2010 12 (8), 1804-1807The resin-supported peptide catalyst having the terminal five-residue Pro-d-Pro-Aib-Trp-Trp combined with polyleucine successfully catalyzed the asymmetric α-oxyamination of aldehydes in aqueous media. The secondary structure and the chirality sense of ...
Enamine Catalysis with Low Catalyst Loadings - High Efficiency via Kinetic Studies
Markus Wiesner, Grégory Upert, Gaetano Angelici and Helma WennemersJournal of the American Chemical Society2010 132 (1), 6-7Enamine Catalysis with Low Catalyst Loadings - High Efficiency via Kinetic Studies
Markus Wiesner, Grégory Upert, Gaetano Angelici and Helma WennemersJournal of the American Chemical Society2010 132 (1), 6-7Kinetic studies on enamine catalysis provided insight into the rate determining step(s) of peptide catalyzed conjugate addition reactions between aldehydes and nitroolefins. They demonstrate that not enamine formation but both the reaction of the enamine ...
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History
- Published In Issue March 17, 2005
- Received January 6, 2005
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