Aqueous microwave-assisted solid-phase peptide synthesis using fmoc strategy. II. Racemization studies and water based synthesis of cysteine-containing peptides

Protein Pept Lett. 2013 Oct;20(10):1122-8. doi: 10.2174/0929866511320100006.

Abstract

We have developed a microwave (MW)-assisted peptide synthesis using Fmoc-amino acid nanoparticles in water previously. It is an organic solvent-free, environmentally friendly method for peptide synthesis. In this study, we have investigated the racemization of cysteine during an aqueous based coupling reaction with MW irradiation. Under our MW-assisted protocol using WSCI and DMTMM, the coupling reaction can be performed with low levels of racemization of cysteine. We also demonstrated the synthesis of the nonapeptide oxytocin analogue, Cys(Acm)-Tyr-Ile-Gln-Asn- Cys(Acm)-Pro-Leu-Gly-NH2 using our water based MW-assisted protocol with Fmoc-amino acid nanoparticles.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Amino Acids / chemical synthesis
  • Amino Acids / chemistry*
  • Cysteine / chemical synthesis
  • Cysteine / chemistry*
  • Fluorenes / chemical synthesis
  • Fluorenes / chemistry*
  • Microwaves
  • Nanoparticles / chemistry*
  • Oxytocin / analogs & derivatives*
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Solid-Phase Synthesis Techniques / methods*
  • Water / chemistry

Substances

  • Amino Acids
  • Fluorenes
  • N(alpha)-fluorenylmethyloxycarbonylamino acids
  • Peptides
  • Water
  • Oxytocin
  • Cysteine