Biosynthetic incorporation of fluorinated amino acids into the nonribosomal peptide gramicidin S
Literature Information
Publication Date
2023-07-25
DOI
10.1039/D3CB00061C
Impact Factor
0
Authors
Maximilian Müll, Farzaneh Pourmasoumi, Leon Wehrhan, Olena Nosovska, Philipp Stephan, Hannah Zeihe, Ivan Vilotijevic, Bettina G. Keller
View Original
Abstract
Fluorine is a key element in medicinal chemistry, as it can significantly enhance the pharmacological properties of drugs. In this study, we aimed to biosynthetically produce fluorinated analogues of the antimicrobial cyclic decapeptide gramicidin S (GS). However, our results show that the A-domain of the NRPS module GrsA rejects 4-fluorinated analogues of its native substrate Phe due to an interrupted T-shaped aromatic interaction in the binding pocket. We demonstrate that GrsA mutant W239S improves the incorporation of 4-fluorinated Phe into GS both in vitro and in vivo. Our findings provide new insights into the behavior of NRPSs towards fluorinated amino acids and strategies for the engineered biosynthesis of fluorinated peptides.
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