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A Novel Synthetic Protocol for the Preparation of Enantiopure 3-, 4-, and 5-Substituted Prolines

  • N. André Sasaki
Part of the Methods in Molecular Medicine™ book series (MIMM, volume 23)

Abstract

Stereochemicaly well-defined 3-, 4-, and 5-monosubstituted prolines can play an important role as probes in search of potent neuroexitatory agents or in the construction of conformationally constrained peptides. Mimicking distinct conformations of excitatory amino acids may lead to a more detailed understanding of the structural requirements for binding of these amino acids to the proteins involved in the process of neurotransmission (1, 2, 3). Meanwhile, syntheses of conformationally constrained peptides are emerging as useful means for developing peptide-derived pharmaceutical agents (4,5). This chapter describes methodology for synthesizing enantiopure 3-, 4-, and 5-monosubstituted prolines starting from the single l-serine-derived chiral derivative (R)-1 (6, 7, 8, 9).

Keywords

Ethyl Acetate Flash Chromatography Benzyl Bromide Allyl Bromide Combine Organic Extract 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Humana Press Inc., Totowa, NJ 1999

Authors and Affiliations

  • N. André Sasaki
    • 1
  1. 1.Institut de Chimie des Substances NaturellesCNRSGifsur-YvetteFrance

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