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Tripeptides of the type H-D-Pro-Pro-Xaa-NH2 as catalysts for asymmetric 1,4-addition reactions: structural requirements for high catalytic efficiency.
Journal article

Tripeptides of the type H-D-Pro-Pro-Xaa-NH2 as catalysts for asymmetric 1,4-addition reactions: structural requirements for high catalytic efficiency.

  • 2009-08-22
Published in:
  • Chemistry (Weinheim an der Bergstrasse, Germany). - 2009
Aldehydes
Amino Acid Sequence
Catalysis
Glutamic Acid
Molecular Conformation
Nitro Compounds
Oligopeptides
Peptide Fragments
Proline
Stereoisomerism
English Analysis of the structural and functional requirements within the asymmetric peptidic catalyst H-D-Pro-Pro-Asp-NH(2) led to the development of the closely related peptide H-D-Pro-Pro-Glu-NH(2) as an even more efficient catalyst for asymmetric conjugate addition reactions of aldehydes to nitroolefins. In the presence of as little as 1 mol % of H-D-Pro-Pro-Glu-NH(2), a broad range of aldehydes and nitroolefins react readily with each other. The resulting gamma-nitroaldehydes were obtained in excellent yields and stereoselectivities at room temperature. Within the structure of the peptidic catalysts, the D-Pro-Pro motif is the major contributor to the high stereoselectivities. The C-terminal amide and the spacer to the carboxylic acid in the side-chain of the C-terminal amino acid are responsible for the fine-tuning of the stereoselectivity. The peptidic catalysts not only allow for highly effective asymmetric catalysis under mild conditions, but also function in the absence of additives.
Language
  • English
Open access status
closed
Identifiers
Persistent URL
https://sonar.ch/global/documents/205247
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