Amino acid building blocks for Fmoc solid-phase synthesis of peptides phosphocholinated at serine, threonine, and tyrosine

J Org Chem. 2013 Mar 15;78(6):2715-9. doi: 10.1021/jo302587g. Epub 2013 Feb 13.

Abstract

Phosphocholination of eukaryotic host cell proteins has recently been identified as a novel post-translational modification important for bacterial pathogenesis. Here, we describe the first straightforward synthetic strategy for peptides containing phosphocholinated serine, threonine, or tyrosine residues using preformed functional amino acid building blocks, fully compatible with standard Fmoc solid-phase peptide synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Fluorenes / chemistry*
  • Peptides / chemical synthesis*
  • Peptides / chemistry*
  • Phosphorylcholine / chemical synthesis*
  • Phosphorylcholine / chemistry*
  • Serine / chemistry*
  • Solid-Phase Synthesis Techniques
  • Threonine / chemistry*
  • Tyrosine / chemistry*

Substances

  • 9-fluorenylmethoxycarbonyl
  • Amino Acids
  • Fluorenes
  • Peptides
  • Phosphorylcholine
  • Threonine
  • Tyrosine
  • Serine