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  Rapid access to glycopeptide antibiotic precursor peptides coupled with cytochrome P450-mediated catalysis: towards a biomimetic synthesis of glycopeptide antibiotics

Brieke, C., Kratzig, V., Haslinger, K., Winkler, A., & Cryle, M. (2015). Rapid access to glycopeptide antibiotic precursor peptides coupled with cytochrome P450-mediated catalysis: towards a biomimetic synthesis of glycopeptide antibiotics. Organic & Biomolecular Chemistry, 13(7), 2012-2021. doi:10.1039/c4ob02452d.

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Datensatz-Permalink: https://hdl.handle.net/11858/00-001M-0000-0024-D2BA-F Versions-Permalink: https://hdl.handle.net/11858/00-001M-0000-0028-A15E-C
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OrgBiomolChem_13_2015_2012.pdf (beliebiger Volltext), 2MB
 
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 Urheber:
Brieke, Clara1, Autor           
Kratzig, Veronika1, Autor           
Haslinger, Kristina1, Autor           
Winkler, Andreas1, Autor           
Cryle, Max1, 2, 3, Autor           
Affiliations:
1Department of Biomolecular Mechanisms, Max Planck Institute for Medical Research, Max Planck Society, ou_1497700              
2Cytochrome P450, Max Planck Institute for Medical Research, Max Planck Society, Jahnstrasse 29, 69120 Heidelberg, DE, ou_1497697              
3Heme and Flavin Enzymes, Max Planck Institute for Medical Research, Max Planck Society, Jahnstrasse 29, 69120 Heidelberg, DE, ou_1497715              

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 Zusammenfassung: Understanding the mechanisms underpinning glycopeptide antibiotic biosynthesis is key to the future ability to reinvent these compounds. For effective in vitro characterization of the crucial later steps of the biosynthesis, facile access to a wide range of substrate peptides as their Coenzyme A (CoA) conjugates is essential. Here we report the development of a rapid route to glycopeptide precursor CoA conjugates that affords both high yields and excellent purities. This synthesis route is applicable to the synthesis of peptide CoA-conjugates containing racemization-prone arylglycine residues: such residues are hallmarks of non-ribosomal peptide synthesis and have previously been inaccessible to peptide synthesis using Fmoc-type chemistry. We have applied this route to generate glycopeptide precursor peptides in their carrier protein-bound form as substrates to explore the specificity of the first oxygenase enzyme from vancomycin biosynthesis (OxyBvan). Our results indicate that OxyBvan is a highly promiscuous catalyst for phenolic coupling of diverse glycopeptide precursors that accepts multiple carrier protein substrates, even on carrier protein domains from alternate glycopeptide biosynthetic machineries. These results represent the first important steps in the development of an in vitro biomimetic synthesis of modified glycopeptide aglycones

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Sprache(n): eng - English
 Datum: 2014-11-212014-12-032015-02-04
 Publikationsstatus: Erschienen
 Seiten: 10
 Ort, Verlag, Ausgabe: -
 Inhaltsverzeichnis: -
 Art der Begutachtung: Expertenbegutachtung
 Identifikatoren: Anderer: 8059
DOI: 10.1039/c4ob02452d
URI: http://www.ncbi.nlm.nih.gov/pubmed/25501135
URI: http://pubs.rsc.org/en/content/articlehtml/2015/ob/c4ob02452d
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Titel: Organic & Biomolecular Chemistry
  Andere : Organic and Biomolecular Chemistry
  Kurztitel : Org. Biomol. Chem.
Genre der Quelle: Zeitschrift
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Ort, Verlag, Ausgabe: Cambridge : Royal Society of Chemistry
Seiten: - Band / Heft: 13 (7) Artikelnummer: - Start- / Endseite: 2012 - 2021 Identifikator: ISSN: 1477-0520
CoNE: https://pure.mpg.de/cone/journals/resource/954925269322