The synthesis of a geminally perfluoro-tert-butylated beta-amino acid and its protected forms as a potential pharmacokinetic modulator and reporter for peptide-based pharmaceuticals

J Org Chem. 2007 Feb 16;72(4):1464-7. doi: 10.1021/jo0616308. Epub 2007 Jan 23.

Abstract

To modulate and report the pharmacokinetics of peptide-based pharmaceuticals, a novel geminally perfluoro-tert-butylated beta-amino acid (betaFa) and its Fmoc- and Boc-protected forms were designed and synthesized. betaFa was incorporated into a model tripeptide via standard solid-phase chemistry. Both the amino acid (free and protected) and the tripeptide show a sharp singlet 19F NMR signal. Reversed-phase chromatography and 1-octanol/water partition measurements demonstrate that betaFa is extremely hydrophobic.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Fluorocarbons / chemistry*
  • Peptides / analysis*
  • Peptides / pharmacokinetics*
  • Protein Conformation

Substances

  • Fluorocarbons
  • Peptides