ArticleAmino acids2016
Incorporation of tryptophan analogues into the lantibiotic nisin.
Article in Amino acids, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed, 42 citations in OpenAlex.
- Synthesis and Antimicrobial Specificities of Halogenated Tryptophan-Containing Nisin Variants.ACS chemical biology · 2025Article
- Functionalizing Nisin with a Sugar Moiety Improves Its Solubility and Results in an Altered Antibacterial Spectrum and Mode of Action.ACS synthetic biology · 2025Article
- Residue-Specific Incorporation of Noncanonical Amino Acids in Auxotrophic Hosts:Chemical reviews · 2025Review
- Facile Halogenation of Antimicrobial Peptides As Demonstrated by Producing Bromotryptophan-Labeled Nisin Variants with Enhanced Antimicrobial Activity.Journal of natural products · 2024Article
- Engineering of Nisin as a Means for Improvement of Its Pharmacological Properties: A Review.Pharmaceuticals (Basel, Switzerland) · 2023Review
- Lipidated variants of the antimicrobial peptide nisin produced via incorporation of methionine analogs for click chemistry show improved bioactivity.The Journal of biological chemistry · 2023Article
- Novel Crown Ether Amino Acids as Fluorescent Reporters for Metal Ions.Molecules (Basel, Switzerland) · 2023Article
- Enhanced Antibacterial Activity of Substituted Derivatives of NCR169C Peptide.International journal of molecular sciences · 2023Article
- Modular Use of the Uniquely Small Ring A of Mersacidin Generates the Smallest Ribosomally Produced Lanthipeptide.ACS synthetic biology · 2022Article
- Nisin Variants Generated by Protein Engineering and Their Properties.Bioengineering (Basel, Switzerland) · 2022Review
- Engineered bacterial host for genetic encoding of physiologically stable protein nitration.Frontiers in molecular biosciences · 2022Article
- Substrate Sequence Controls Regioselectivity of Lanthionine Formation by ProcM.Journal of the American Chemical Society · 2021Article
- New developments in RiPP discovery, enzymology and engineering.Natural product reports · 2021Review
- Expanding the Scope of Orthogonal Translation with Pyrrolysyl-tRNA Synthetases Dedicated to Aromatic Amino Acids.Molecules (Basel, Switzerland) · 2020Article
- Substrate Recognition by the Class II Lanthipeptide Synthetase HalM2.ACS chemical biology · 2020Article
- Site-specific 5-hydroxytryptophan incorporation into apolipoprotein A-I impairs cholesterol efflux activity and high-density lipoprotein biogenesis.The Journal of biological chemistry · 2020Article
- Combating Antimicrobial Resistance With New-To-Nature Lanthipeptides Created by Genetic Code Expansion.Frontiers in microbiology · 2020Review
- Systematic characterization of position one variants within the lantibiotic nisin.Scientific reports · 2019Article
- High-resolution NMR studies of antibiotics in cellular membranes.Nature communications · 2018Article
- Catalytic Modification of Dehydroalanine in Peptides and Proteins by Palladium-Mediated Cross-Coupling.Chemistry (Weinheim an der Bergstrasse, Germany) · 2018Article
Corrections and comments
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Authors and funding
7 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Lantibiotics are posttranslationally modified peptides with efficient inhibitory activity against various Gram-positive bacteria. In addition to the original modifications, incorporation of non-canonical amino acids can render new properties and functions to lantibiotics. Nisin is the most studied lantibiotic and contains no tryptophan residues. In this study, a system was constructed to incorporate tryptophan analogues into nisin, which included the modification machinery (NisBTC) and the overexpression of tryptophanyl-tRNA synthetase (TrpRS). Tryptophan and three different tryptophan analogues (5-fluoroTrp (5FW), 5-hydroxyTrp (5HW) and 5-methylTrp (5MeW)) were successfully incorporated at four different positions of nisin (I1W, I4W, M17W and V32W). The incorporation efficiency of tryptophan analogues into mutants I1W, M17W and V32W was over 97 %, while the mutant I4W showed relatively low incorporation efficiency (69-93 %). The variants with 5FW showed relatively higher production yield, while 5MeW-containing variants showed the lowest yield. The dehydration efficiency of serines or threonines was affected by the tryptophan mutants of I4W and V32W. The affinity of the peptides for the cation-ion exchange and reverse phase chromatography columns was significantly reduced when 5HW was incorporated. The antimicrobial activity of IIW and its 5FW analogue both decreased two times compared to that of nisin, while that of its 5HW analogue decreased four times. The 5FW analogue of I4W also showed two times decreased activity than nisin. However, the mutant M17W and its 5HW analogue both showed 32 times reduced activity relative to that of nisin.
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