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  Sequential in vitro cyclization by cytochrome P450 enzymes of glycopeptide antibiotic precursors bearing the X-domain from nonribosomal peptide biosynthesis

Brieke, C., Peschke, M., Haslinger, K., & Cryle, M. J. (2015). Sequential in vitro cyclization by cytochrome P450 enzymes of glycopeptide antibiotic precursors bearing the X-domain from nonribosomal peptide biosynthesis. Angewandte Chemie International Edition in English, 54(52), 15715-15719. doi:10.1002/anie.201507533.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-002A-21A0-D Version Permalink: https://hdl.handle.net/11858/00-001M-0000-002A-21A1-B
Genre: Journal Article

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 Creators:
Brieke, Clara1, Author           
Peschke, Madeleine1, Author           
Haslinger, Kristina1, Author           
Cryle, Max J.1, Author           
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1Department of Biomolecular Mechanisms, Max Planck Institute for Medical Research, Max Planck Society, ou_1497700              

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 Abstract: The biosynthesis of the glycopeptide antibiotics, which include vancomycin and teicoplanin, relies on the interplay between the peptide-producing non-ribosomal peptide synthetase (NRPS) and Cytochrome P450 enzymes (P450s) that catalyze side-chain crosslinking of the peptide. We demonstrate that sequential in vitro P450-catalyzed cyclization of peptide substrates is enabled by the use of an NRPS peptide carrier protein (PCP)-X di-domain as a P450 recruitment platform. This study reveals that whilst the precursor peptide sequence influences the installation of the second crosslink by the P450 OxyAtei , activity is not restricted to the native teicoplanin peptide. Initial peptide cyclization is possible with teicoplanin and vancomycin OxyB homologues, and the latter displays excellent activity with all substrate combinations tested. By using non-natural X-domain substrates, bicyclization of hexapeptides was also shown, which demonstrates the utility of this method for the cyclization of varied peptide substrates in vitro.

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Language(s): eng - English
 Dates: 2015-08-152015-11-092015-11-092015-12-21
 Publication Status: Issued
 Pages: 5
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 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201507533
URI: http://www.ncbi.nlm.nih.gov/pubmed/26549530
URI: http://onlinelibrary.wiley.com/doi/10.1002/anie.201507533/abstract
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Title: Angewandte Chemie International Edition in English
  Other : Angewandte Chemie, International Edition in English
  Abbreviation : Angew. Chem. Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 54 (52) Sequence Number: - Start / End Page: 15715 - 15719 Identifier: ISSN: 0570-0833
CoNE: https://pure.mpg.de/cone/journals/resource/0570-0833