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

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

Journal Name: Protein & Peptide Letters

Volume 20 , Issue 10 , 2013

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.

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

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Article Details

VOLUME: 20
ISSUE: 10
Year: 2013
Page: [1122 - 1128]
Pages: 7
DOI: 10.2174/0929866511320100006

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