Zinc-promoted simple synthesis of oligomer-free N(alpha)-Fmoc-amino acids using Fmoc-Cl as an acylating agent under neutral conditions

J Pept Res. 2000 Apr;55(4):295-9. doi: 10.1034/j.1399-3011.2000.00668.x.

Abstract

A range of N(alpha)-Fmoc-protected amino acids, including those that contain t-butyl moiety, have been synthesized by employing Fmoc-Cl utilizing the activated, commercial zinc dust-promoted synthesis of carbamates under neutral conditions. A general procedure is described that circumvents the oligomerization side reaction normally noticed in Schotten-Baumann conditions. It is a simple, convenient and clean method. Thus, Fmoc-amino acids are obtained in high yield (85-92%) and purity as checked by thin-layer chromatography, high-performance liquid chromatography and other physical methods.

MeSH terms

  • Acylation
  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Carbamates / chemistry
  • Chromatography, High Pressure Liquid
  • Chromatography, Thin Layer
  • Fluorenes / chemical synthesis*
  • Fluorenes / chemistry
  • Zinc

Substances

  • Amino Acids
  • Carbamates
  • Fluorenes
  • N(alpha)-fluorenylmethyloxycarbonylamino acids
  • Zinc