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Updated: Apr 27, 2026
An Inexpensive Adaptation of a Commercial Microwave Reactor for Solid Phase Peptide Synthesis
Published on: November 22, 2024
Aqueous microwave-assisted solid-phase peptide synthesis using Fmoc strategy. III: racemization studies and
Keiko Hojo1, Natsuki Shinozaki, Koushi Hidaka
1Faculty of Pharmaceutical Sciences and Cooperative Research Center of Life Sciences, Kobe Gakuin University, Chuo-ku, Kobe, 650-8586, Japan, hojo@pharm.kobegakuin.ac.jp.
Abstract:
In this study, we describe the first aqueous microwave-assisted synthesis of histidine-containing peptides in high purity and with low racemization. We have previously shown the effectiveness of our synthesis methodology for peptides including difficult sequences using water-dispersible 9-fluorenylmethoxycarbonyl-amino acid nanoparticles. It is an organic solvent-free, environmentally friendly method for chemical peptide synthesis. Here, we studied the racemization of histidine during an aqueous-based coupling reaction with microwave irradiation. Under our microwave-assisted protocol using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride, the coupling reaction can be efficiently performed with low levels of racemization of histidine. Application of this water-based microwave-assisted protocol with water-dispersible 9-fluorenylmethoxycarbonyl-amino acid nanoparticles led to the successful synthesis of the histidine-containing hexapeptide neuropeptide W-30 (10-15), Tyr-His-Thr-Val-Gly-Arg-NH₂, in high yield and with greatly reduced histidine racemization.
