A Chemoenzymatic Approach to the Synthesis of Glycopeptide Antibiotic Analogues.
biocatalysis
biosynthesis
cytochrome P450 enzymes
glycopeptide antibiotics
nonribosomal peptides
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
26 06 2020
26 06 2020
Historique:
received:
12
03
2020
revised:
14
04
2020
pubmed:
17
4
2020
medline:
18
3
2021
entrez:
17
4
2020
Statut:
ppublish
Résumé
Glycopeptide antibiotics (GPAs) are important antibiotics that are highly challenging to synthesise due to their unique and heavily crosslinked structure. Given this, the synthetic production and diversification of this key compound class remains impractical. Furthermore, the possibility of biosynthetic reengineering of GPAs is not yet feasible since the selectivity of the biosynthetic crosslinking enzymes for altered substrates is largely unknown. We show that combining peptide synthesis with enzymatic cyclisation enables the formation of novel examples of GPAs and provides an indication of the utility of these crucial enzymes. By accessing the biosynthetic process in vitro, we identified peptide modifications that are enzymatically tolerated and can also reveal the mechanistic basis for substrate intolerance where present. Using this approach, we next specifically activated modified residues within GPAs for functionalisation at previously inaccessible positions, thereby offering the possibility of late-stage chemical functionalisation after GPA cyclisation is complete.
Identifiants
pubmed: 32297389
doi: 10.1002/anie.202003726
doi:
Substances chimiques
Anti-Bacterial Agents
0
Glycopeptides
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
10899-10903Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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