Iron‐Catalyzed Biomimetic Dimerization of Tryptophan‐Containing Peptides
Abstract: Biomimetic oxidative dimerization of tryptophan derivatives in aqueous media with oxygen as a bulk oxidant catalyzed by an iron octacarboxy phthalocyanine complex was established. The discovery of the extremely active iron catalyst enables aerobic enzyme‐mimetic oxidation to be performed in a flask. This method was applicable to the oxidative dimerization of a wide range of tryptophan derivatives, including various dipeptides and oligopeptides, with remarkable functional‐group tolerance without the protection of the amino acid residues. Furthermore, oxidative dimerization of tryptophan derivatives bearing dioxopiperazine units enabled the convergent total synthesis of five natural pyrroloindole compounds and unnatural congeners. The established chemical method provides facile access to a broad range of dimerized peptides with a unique scaffold to link two turn structures, which will serve as a powerful tool to create new small‐ and medium‐sized‐molecules as drug candidates.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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Iron‐Catalyzed Biomimetic Dimerization of Tryptophan‐Containing Peptides ; day:21 ; month:04 ; year:2023 ; extent:10
Angewandte Chemie ; (21.04.2023) (gesamt 10)
- Urheber
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Ueda, Hirofumi
Sato, Soichiro
Noda, Kenta
Hakamata, Hiroyuki
Kwon, Eunsang
Kobayashi, Nagao
Tokuyama, Hidetoshi
- DOI
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10.1002/ange.202302404
- URN
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urn:nbn:de:101:1-2023042415484592421948
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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14.08.2025, 10:57 MESZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Ueda, Hirofumi
- Sato, Soichiro
- Noda, Kenta
- Hakamata, Hiroyuki
- Kwon, Eunsang
- Kobayashi, Nagao
- Tokuyama, Hidetoshi
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PolyQ aggregation studied by model peptides with intrinsic tryptophan fluorophores
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Identifizierung von Tryptophanderivaten in Tryptophan, tryptophanhaltigen Peptiden und Proteinen : = Identification of contaminants in biotechnologically manufactured tryptophan and oxidation of tryptophan residues in peptides and proteins
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