Cytochrome P450 Blt Enables Versatile Peptide Cyclisation to Generate Histidine‐ and Tyrosine‐Containing Crosslinked Tripeptide Building Blocks

Abstract: We report our investigation of the utility of peptide crosslinking cytochrome P450 enzymes from biarylitide biosynthesis to generate a range of cyclic tripeptides from simple synthons. The crosslinked tripeptides produced by this P450 include both tyrosine‐histidine (A−N−B) and tyrosine‐tryptophan (A−O−B) crosslinked tripeptides, the latter a rare example of a phenolic crosslink to an indole moiety. Tripeptides are easily isolated following proteolytic removal of the leader peptide and can incorporate a wide range of amino acids in the residue inside the crosslinked tripeptide. Given the utility of peptide crosslinks in important natural products and the synthetic challenge that these can represent, P450 enzymes have the potential to play roles as important tools in the generation of high‐value cyclic tripeptides for incorporation in synthesis, which can be yet further diversified using selective chemical techniques through specific handles contained within these tripeptides.

Angaben zum Objekt

• Standort: Deutsche Nationalbibliothek Frankfurt am Main
• Umfang: Online-Ressource
• Sprache: Englisch

Verweise und Beziehungen

• Erschienen in: Cytochrome P450 Blt Enables Versatile Peptide Cyclisation to Generate Histidine‐ and Tyrosine‐Containing Crosslinked Tripeptide Building Blocks ; day:03 ; month:08 ; year:2022 ; extent:1 ; Angewandte Chemie / International edition. International edition ; (03.08.2022) (gesamt 1)

Beteiligte, Orts- und Zeitangaben

• Urheber: Zhao, Yongwei ; Marschall, Edward ; Treisman, Maxine ; McKay, Alasdair ; Padva, Leo ; Crüsemann, Max ; Nelson, David R. ; Steer, David L. ; Schittenhelm, Ralf B. ; Tailhades, Julien ; Cryle, Max

Weitere Informationen

• DOI: 10.1002/anie.202204957
• URN: urn:nbn:de:101:1-2022080415223402049785
• Rechteinformation: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Letzte Aktualisierung: 15.08.2025, 07:29 MESZ