Robust asymmetric synthesis of unnatural alkenyl amino acids for conformationally constrained α-helix peptides

Org Biomol Chem. 2014 Nov 21;12(43):8775-82. doi: 10.1039/c4ob01832j.

Abstract

The efficient asymmetric synthesis of unnatural alkenyl amino acids required for peptide 'stapling' has been achieved using alkylation of a fluorine-modified Ni(II) Schiff base complex as the key step.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Amino Acids / chemistry*
  • Catalysis
  • Cations, Divalent
  • Crystallography, X-Ray
  • Fluorine / chemistry*
  • Halogenation
  • Molecular Mimicry
  • Nickel / chemistry*
  • Peptides / chemical synthesis*
  • Peptidomimetics / chemical synthesis*
  • Protein Structure, Secondary
  • Schiff Bases / chemistry*
  • Stereoisomerism

Substances

  • Amino Acids
  • Cations, Divalent
  • Peptides
  • Peptidomimetics
  • Schiff Bases
  • Fluorine
  • Nickel