ArticleJournal of the American Chemical Society2013
Chemical synthesis of the lantibiotic lacticin 481 reveals the importance of lanthionine stereochemistry.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed, 58 citations in OpenAlex.
- Cyanamide-Induced Desulfhydration Enables Access to α,β-Dehydropeptides.Organic letters · 2026Article
- Discovery, Biosynthesis, and Characterization of Rodencin, a Two-Component Lanthipeptide, Harboring d-Amino Acids Introduced by the Unusual Dehydrogenase RodJJournal of natural products · 2024Article
- Article
- Facile Method for Determining Lanthipeptide Stereochemistry.Analytical chemistry · 2024Article
- Systematic mining of the human microbiome identifies antimicrobial peptides with diverse activity spectra.Nature microbiology · 2023Article
- Synthesis of Fluorescent Lanthipeptide Cytolysin S Analogues by Late-Stage Sulfamidate Ring Opening.Organic letters · 2023Article
- Divergent Evolution of Lanthipeptide Stereochemistry.ACS chemical biology · 2022Article
- Metabolic Processing of Selenium-Based Bioisosteres ofBiochemistry · 2022Article
- Unexpected Methyllanthionine Stereochemistry in the Morphogenetic Lanthipeptide SapT.Journal of the American Chemical Society · 2022Article
- Evaluation of endogenous peptide stereochemistry using liquid chromatography-mass spectrometry-based spiking experiments.Methods in enzymology · 2022Article
- Facile Synthesis and Metabolic Incorporation ofACS chemical biology · 2020Article
- A Chemical Biology Approach to Understanding Molecular Recognition of Lipid II by Nisin(1-12): Synthesis and NMR Ensemble Analysis of Nisin(1-12) and Analogues.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
- Molecular Recognition of Lipid II by Lantibiotics: Synthesis and Conformational Studies of Analogues of Nisin and Mutacin Rings A and B.The Journal of organic chemistry · 2019Article
- Scalable Synthesis of Orthogonally Protected β-Methyllanthionines by Indium(III)-Mediated Ring Opening of Aziridines.Organic letters · 2019Article
- pDobz/pDobb protected diaminodiacid as a novel building block for peptide disulfide-bond mimic synthesis.RSC advances · 2019Article
- Genome mining, isolation, chemical synthesis and biological evaluation of a novel lanthipeptide, tikitericin, from the extremophilic microorganismChemical science · 2018Article
- Nisin Z produced by Lactococcus lactis from bullfrog hatchery is active against Citrobacter freundii, a red-leg syndrome related pathogen.World journal of microbiology & biotechnology · 2017Article
- Mechanistic Understanding of Lanthipeptide Biosynthetic Enzymes.Chemical reviews · 2017Review
- Synthesis and Bioactivity of Diastereomers of the Virulence Lanthipeptide Cytolysin.Organic letters · 2016Article
- Lanthipeptides: chemical synthesis versus in vivo biosynthesis as tools for pharmaceutical production.Microbial cell factories · 2016Review
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Lantibiotics are a family of antibacterial peptide natural products characterized by the post-translational installation of the thioether-containing amino acids lanthionine and methyllanthionine. Until recently, only a single naturally occurring stereochemical configuration for each of these cross-links was known. The discovery of lantibiotics with alternative lanthionine and methyllanthionine stereochemistry has prompted an investigation of its importance to biological activity. Here, solid-supported chemical synthesis enabled the total synthesis of the lantibiotic lacticin 481 and analogues containing cross-links with non-native stereochemical configurations. Biological evaluation revealed that these alterations abolished the antibacterial activity in all of the analogues, revealing the critical importance of the enzymatically installed stereochemistry for the biological activity of lacticin 481.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.