Solid-phase synthesis of phenylalanine containing peptides using a traceless triazene linker

J Org Chem. 2012 Nov 2;77(21):9852-8. doi: 10.1021/jo301630h. Epub 2012 Oct 24.

Abstract

The use of a triazene function to anchor phenylalanine to a polymeric support through its side chain is reported. To prove the usefulness of this strategy in solid-phase peptide synthesis, several bioactive peptides have been prepared including cyclic, C-modified, and protected peptides. The triazene linkage is formed by coupling the diazonium salt of Fmoc-Phe(pNH(2))-OAllyl to a MBHA-polystyrene resin previously functionalized with isonipecotic acid (90%). Further assembly of the peptide chain, cleavage from the resin using 2-5% TFA in DCM, and reduction of the resulting diazonium salt of the peptide with FeSO(4)·7H(2)O in DMF afforded the desired products in high purities (73-94%).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Chromatography, High Pressure Liquid
  • Molecular Sequence Data
  • Peptides / chemical synthesis
  • Peptides / chemistry
  • Phenylalanine / chemical synthesis*
  • Phenylalanine / chemistry*
  • Solid-Phase Synthesis Techniques / methods*
  • Triazines / chemistry*

Substances

  • Peptides
  • Triazines
  • Phenylalanine