Journal
AMINO ACIDS
Volume 46, Issue 10, Pages 2347-2354Publisher
SPRINGER WIEN
DOI: 10.1007/s00726-014-1779-y
Keywords
Histidine; Microwave-assisted synthesis; Nanoparticles; Racemization; Solid-phase peptide synthesis; Synthesis in water
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Funding
- Strategic Research Foundation at Private Universities matching fund subsidy from the Japanese Ministry of Education, Culture, Sports Science and Technology [S1201010]
- Takeda Science Foundation
- Victorian Government Operational Infrastructure Support Program
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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.
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