![4-[(2-Fluoro-4-methylphenyl)amino]-6-[4-(2-hydroxyethyl)-1-piperazinyl]-7-methoxy-3-cinnolinecarboxamide structure](https://static.chemtradehub.com/structs/104/1041852-85-0-fb1c.webp "4-[(2-Fluoro-4-methylphenyl)amino]-6-[4-(2-hydroxyethyl)-1-piperazinyl]-7-methoxy-3-cinnolinecarboxamide structure")
4-[(2-Fluoro-4-methylphenyl)amino]-6-[4-(2-hydroxyethyl)-1-piperazinyl]-7-methoxy-3-cinnolinecarboxamide
CAS Number:
1041852-85-0
Molecular Formula:
C23H27FN6O3
Synthesis and biological evaluation of coprinoferrin, an acylated tripeptide hydroxamate siderophore
Literature Information
Publication Date
2023-12-21
DOI
10.1039/D3OB01850D
Impact Factor
3.876
Authors
Ichiro Hayakawa, Tomoki Isogai, Jun Takanishi, Shihori Asai, Chika Ando, Tomohiro Tsutsumi, Kenji Watanabe, Akira Sakakura, Yuta Tsunematsu
View Original
Abstract
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-hexanoyl-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 provides unequivocal confirmation of the proposed chemical structure, facilitating a deeper understanding of its physiological role in nature, particularly in fruiting body formation.
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Source Journal
Organic & Biomolecular Chemistry
CiteScore:
3.4
Self-citation Rate:
10.3%
Articles per Year:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
Recommended Compounds
![(2S)-2-({N-[(2S)-2-Ammonio-4-methylpentanoyl]glycyl}amino)-3-phenylpropanoate structure](https://static.chemtradehub.com/structs/429/4294-25-1-0842.webp "(2S)-2-({N-[(2S)-2-Ammonio-4-methylpentanoyl]glycyl}amino)-3-phenylpropanoate structure")
(2S)-2-({N-[(2S)-2-Ammonio-4-methylpentanoyl]glycyl}amino)-3-phenylpropanoate
CAS Number:
4294-25-1
Molecular Formula:
C17H25N3O4
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