Journal
ACS CHEMICAL BIOLOGY
Volume 16, Issue 6, Pages 1019-1029Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acschembio.1c00106
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Funding
- National Institutes of Health [GM 058822, F32 GM117765, S10 RR027109 A]
- national funds (OE), through FCT [4, 5, 6, 23, CEECIND/01463/2017]
- FCT/MCTES [UIDP/50017/2020, UIDB/50017/2020]
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Lanthipeptides are a type of ribosomally synthesized and post-translationally modified peptide natural products characterized by lanthionine and methyllanthionine crosslinked amino acids. While most lanthipeptides are identified from Gram-positive bacteria, this study reports the heterologous expression and modification in Escherichia coli of two lanthipeptides from the Gram-negative Bacteroidetes Pedobacter lusitanus NL19, showing novel structural features and unusual stereochemical configuration.
Lanthipeptides are ribosomally synthesized and post-translationally modified peptide natural products characterized by the presence of lanthionine and methyllanthionine crosslinked amino acids formed by dehydration of Ser/Thr residues followed by conjugate addition of Cys to the resulting dehydroamino acids. Class I lanthipeptide dehydratases utilize glutamyl-tRNAGlu as a cosubstrate to glutamylate Ser/Thr followed by glutamate elimination. A vast majority of lanthipeptides identified from class I synthase systems have been from Gram-positive bacteria. Herein, we report the heterologous expression and modification in Escherichia coli of two lanthipeptides from the Gram-negative Bacteroidetes Pedobacter lusitanus NL19. These peptides are representative of a group of compounds frequently encoded in Pedobacter genomes. Structural characterization of the lanthipeptides revealed a novel ring pattern as well as an unusual LL-lanthionine stereochemical configuration and a cyclase that lacks the canonical zinc ligands found in most LanC enzymes.
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