ArticleJournal of the American Society for Mass Spectrometry2011
Topoisomer differentiation of molecular knots by FTICR MS: lessons from class II lasso peptides.
Article in Journal of the American Society for Mass Spectrometry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed, 40 citations in OpenAlex.
- Chemoenzymatic Modification of Microcin J25 with Single-Residue Precision Provides New-to-Nature Lasso Peptides.JACS Au · 2026Article
- Synthesis of β-Thiolated Amino Acids: Investigation Toward the Total Chemical Synthesis of Lasso Peptide Microcin J25.Chembiochem : a European journal of chemical biology · 2026Article
- Uncovering how selected potent bacteriocins reshape the broiler chicken gut microbiome in a PolyFermS continuous in vitro model.Journal of animal science and biotechnology · 2026Article
- Genomic Insight intoBioengineering (Basel, Switzerland) · 2022Article
- Exploring structural signatures of the lanthipeptide prochlorosin 2.8 using tandem mass spectrometry and trapped ion mobility-mass spectrometry.Analytical and bioanalytical chemistry · 2021Article
- Recent Advances and Perspectives on Expanding the Chemical Diversity of Lasso Peptides.Frontiers in bioengineering and biotechnology · 2021Review
- Discovery of Ubonodin, an Antimicrobial Lasso Peptide Active against Members of the Burkholderia cepacia Complex.Chembiochem : a European journal of chemical biology · 2020Article
- Evidence of Cis/Trans-Isomerization at Pro7/Pro16 in the Lasso Peptide Microcin J25.Journal of the American Society for Mass Spectrometry · 2019Article
- Conformational dynamics of the ABC transporter McjD seen by single-molecule FRET.The EMBO journal · 2018Article
- An orthogonal system for heterologous expression of actinobacterial lasso peptides in Streptomyces hosts.Scientific reports · 2018Article
- Fate and Biological Activity of the Antimicrobial Lasso Peptide Microcin J25 Under Gastrointestinal Tract Conditions.Frontiers in microbiology · 2018Article
- Structural basis for antibacterial peptide self-immunity by the bacterial ABC transporter McjD.The EMBO journal · 2017Article
- Thermal Unthreading of the Lasso Peptides Astexin-2 and Astexin-3.ACS chemical biology · 2016Article
- Structural and Functional Basis for Lipid Synergy on the Activity of the Antibacterial Peptide ABC Transporter McjD.The Journal of biological chemistry · 2016Article
- Structural basis for hijacking siderophore receptors by antimicrobial lasso peptides.Nature chemical biology · 2014Article
- Precursor-centric genome-mining approach for lasso peptide discovery.Proceedings of the National Academy of Sciences of the United States of America · 2012Article
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Authors and funding
7 authors at 4 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Lasso peptides constitute a class of bioactive peptides sharing a knotted structure where the C-terminal tail of the peptide is threaded through and trapped within an N-terminal macrolactam ring. The structural characterization of lasso structures and differentiation from their unthreaded topoisomers is not trivial and generally requires the use of complementary biochemical and spectroscopic methods. Here we investigated two antimicrobial peptides belonging to the class II lasso peptide family and their corresponding unthreaded topoisomers: microcin J25 (MccJ25), which is known to yield two-peptide product ions specific of the lasso structure under collision-induced dissociation (CID), and capistruin, for which CID does not permit to unambiguously assign the lasso structure. The two pairs of topoisomers were analyzed by electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry (ESI-FTICR MS) upon CID, infrared multiple photon dissociation (IRMPD), and electron capture dissociation (ECD). CID and ECD spectra clearly permitted to differentiate MccJ25 from its non-lasso topoisomer MccJ25-Icm, while for capistruin, only ECD was informative and showed different extent of hydrogen migration (formation of c•/z from c/z•) for the threaded and unthreaded topoisomers. The ECD spectra of the triply-charged MccJ25 and MccJ25-lcm showed a series of radical b-type product ions (b'/•(n)). We proposed that these ions are specific of cyclic-branched peptides and result from a dual c/z• and y/b dissociation, in the ring and in the tail, respectively. This work shows the potentiality of ECD for structural characterization of peptide topoisomers, as well as the effect of conformation on hydrogen migration subsequent to electron capture.
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