{"id":412,"date":"2024-01-22T09:48:11","date_gmt":"2024-01-22T00:48:11","guid":{"rendered":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/?p=412"},"modified":"2025-06-13T11:01:52","modified_gmt":"2025-06-13T02:01:52","slug":"%e3%80%90%e6%96%b0%e7%9d%80%e8%ab%96%e6%96%87%e3%80%91synthesis-and-biological-evaluation-of-coprinoferrin-an-acylated-tripeptide-hydroxamate-siderophore","status":"publish","type":"post","link":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/archives\/412","title":{"rendered":"\u3010\u65b0\u7740\u8ad6\u6587\u3011Synthesis and biological evaluation of coprinoferrin, an acylated tripeptide hydroxamate siderophore"},"content":{"rendered":"\n<p class=\"has-small-font-size\">Ichiro Hayakawa*,&nbsp;Tomoki Isogai, Jun Takanishi,&nbsp;Shihori Asai,&nbsp;Chika Ando,&nbsp;Tomohiro Tsutsumi,&nbsp;Kenji Watanabe*,&nbsp;Akira Sakakura*&nbsp;and<br>Yuta Tsunematsu*<br><em>Org. Biomol. Chem. <\/em><strong>2024<\/strong><em>, Advance Article<\/em><br>DOI:&nbsp;<a rel=\"noreferrer noopener\" href=\"https:\/\/pubs.rsc.org\/en\/content\/articlehtml\/2024\/ob\/d3ob01850d\" target=\"_blank\">10.1039\/D3OB01850D<\/a><\/p>\n\n\n\n<p>Coprinoferrin (CPF), originally isolated from a genetically engineered strain (\u0394laeA) of the mushroom fungus&nbsp;Coprinopsis cinerea, is an acylated tripeptide hydroxamate consisting of tandem aligned&nbsp;N5-hexa- noyl-N5-hydroxy-L-ornithine with modifications of&nbsp;N-acetyl and&nbsp;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&nbsp;C. cinerea. However, CPF\u2019s detailed mode of action remains enigmatic. In this study, we have accomplished the synthesis of CPF from&nbsp;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.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Ichiro Hayakawa*,&nbsp;Tomoki Isogai, Jun Takanishi,&nbsp;Shihori Asai,&nbsp;Chika Ando,&nbsp;Tomohiro Tsutsum [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"vkexunit_cta_each_option":"","footnotes":""},"categories":[4,6],"tags":[],"class_list":["post-412","post","type-post","status-publish","format-standard","hentry","category-news","category-publications"],"_links":{"self":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/412","targetHints":{"allow":["GET"]}}],"collection":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/comments?post=412"}],"version-history":[{"count":1,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/412\/revisions"}],"predecessor-version":[{"id":414,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/412\/revisions\/414"}],"wp:attachment":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media?parent=412"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/categories?post=412"},{"taxonomy":"post_tag","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/tags?post=412"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}