2013•Protein and Peptide LettersRequires access

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

Keiko Hojo, Natsuki Shinozaki, Asaki Hara, Mare Onishi, Yoshinobu Fukumori, Hideki Ichikawa

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.

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Key concepts: Racemization, Peptide synthesis, Chemistry, Solid-phase synthesis, Peptide, Cysteine, Amino acid, Aqueous solution