【新着論文】Synthesis and biological evaluation of coprinoferrin, an acylated tripeptide hydroxamate siderophore

Ichiro Hayakawa*, Tomoki Isogai, Jun Takanishi, Shihori Asai, Chika Ando, Tomohiro Tsutsumi, Kenji Watanabe*, Akira Sakakura* and
Yuta Tsunematsu*
Org. Biomol. Chem. 2024, Advance Article
DOI: 10.1039/D3OB01850D

Coprinoferrin (CPF), originally isolated from a genetically engineered strain (ΔlaeA) of the mushroom fungus Coprinopsis cinerea, is an acylated tripeptide hydroxamate consisting of tandem aligned N5-hexa- noyl-N5-hydroxy-L-ornithine with modifications of N-acetyl and C-carboxamide. These unique chemical properties make CPF an iron(III) binder (siderophore), which helps in iron acquisition from the environment and promotes hyphal growth as well as fruiting body formation in C. cinerea. However, CPF’s detailed mode of action remains enigmatic. In this study, we have accomplished the synthesis of CPF from N-Boc-L-glutamic acid 5-benzyl ester. The physicochemical characteristics, spectroscopic features, and biological activity observed in the synthetic CPF closely match those of natural CPF. This alignment pro- vides unequivocal confirmation of the proposed chemical structure, facilitating a deeper understanding of its physiological role in nature, particularly in fruiting body formation.