Molecules (Mar 2024)

Asymmetric α-Fluoroalkyl-α-Amino Acids: Recent Advances in Their Synthesis and Applications

  • Nathan Picois,
  • Yazid Boutahri,
  • Pierre Milbeo,
  • Chiara Zanato,
  • Nathalie Lensen,
  • Grégory Chaume,
  • Thierry Brigaud

DOI
https://doi.org/10.3390/molecules29061408
Journal volume & issue
Vol. 29, no. 6
p. 1408

Abstract

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Due to the specific properties provided by fluorine atoms to biomolecules, amino acids with fluorinated side chains are of great interest for medicinal chemistry and chemical biology. Among them, α-fluoroalkyl-α-amino acids constitute a unique class of compounds. In this review, we outline the strategies adopted for their syntheses in enantiopure or enantioenriched forms and their incorporation into peptides. We then describe the consequences of the introduction of fluorine atoms in these compounds for the modulation of their hydrophobicity and the control of their conformation. Emerging applications are presented in the areas of enzyme inhibition, medicinal chemistry, hydrolytic stability of peptides, antimicrobial peptides, PET, and 19F NMR probes.

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