Aqueous Microwave-Assisted Solid-Phase Peptide Synthesis Using Fmoc Strategy. II. Racemization Studies and Water Based Synthesis of Cysteine- Containing Peptides

Title:Aqueous Microwave-Assisted Solid-Phase Peptide Synthesis Using Fmoc Strategy. II. Racemization Studies and Water Based Synthesis of Cysteine- Containing Peptides

Volume: 20 Issue: 10

Author(s): Keiko Hojo, Natsuki Shinozaki, Asaki Hara, Mare Onishi, Yoshinobu Fukumori and Hideki Ichikawa

Affiliation:

Keywords: Cysteine, microwave-assisted synthesis, nanoparticles, racemization solid-phase peptide synthesis, synthesis in water.

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.

Cite this article as:

Hojo Keiko, Shinozaki Natsuki, Hara Asaki, Onishi Mare, Fukumori Yoshinobu and Ichikawa Hideki, Aqueous Microwave-Assisted Solid-Phase Peptide Synthesis Using Fmoc Strategy. II. Racemization Studies and Water Based Synthesis of Cysteine- Containing Peptides, Protein & Peptide Letters 2013; 20 (10) . https://dx.doi.org/10.2174/0929866511320100006