Abstract
A versatile solid-phase total synthesis was applied to the rapid preparation of Argadin, a natural product isolated and characterized as a cyclopentapeptide by our group, which possesses superior inhibitory activity against family-18 chitinases. The synthetic strategy includes peptide synthesis by using an Fmoc (9-fluorenylmethoxycarbonyl) protective group, macrolactamization, acetylguanylation and formation of hemiaminal accompanied by total deprotection, including cleavage from resin.
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Acknowledgements
This work was supported by the Grant of the 21st Century COE Program, Ministry of Education Culture, Sports, Science and Technology. AS was supported by a JSPS Research Fellowships for Young Scientists. TH acknowledges the Kitasato University research grant for young researchers. We also thank Ms A Nakagawa, Ms N Sato and Dr K Nagai (Kitasato University) for various instrumental analyses.
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Hirose, T., Sunazuka, T., Sugawara, A. et al. Solid-phase total synthesis of the chitinase inhibitor Argadin using a supported acetal resin. J Antibiot 62, 495–500 (2009). https://doi.org/10.1038/ja.2009.57
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DOI: https://doi.org/10.1038/ja.2009.57
