ArticleThe Journal of biological chemistry2014
Semienzymatic cyclization of disulfide-rich peptides using Sortase A.
Article in The Journal of biological chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 29 papers.
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Who cites it
29 citing papers in PubMed, 92 citations in OpenAlex.
- Exploring Use of a Protein Cage System for Producing Bioactive Peptides in Escherichia coli.Microbial biotechnology · 2025Article
- Review
- Diol as a New Pantetheine Surrogate for Chemoenzymatic Synthesis of Cyclic Peptides via Nonribosomal Peptide Cyclases.Methods in molecular biology (Clifton, N.J.) · 2025Article
- Azole reagents enabled ligation of peptide acyl pyrazoles for chemical protein synthesis.Chemical science · 2024Article
- Chemoenzymatic tandem cyclization for the facile synthesis of bicyclic peptides.Communications chemistry · 2024Article
- Going Beyond Host Defence Peptides: Horizons of Chemically Engineered Peptides for Multidrug-Resistant Bacteria.BioDrugs : clinical immunotherapeutics, biopharmaceuticals and gene therapy · 2023Review
- Insights into the synthesis strategies of plant-derived cyclotides.Amino acids · 2023Review
- Exploring the Limits of Cyanobactin Macrocyclase PatGmac: Cyclization of PawS-Derived Peptide Sunflower Trypsin Inhibitor-1 and Cyclotide Kalata B1.Journal of natural products · 2023Article
- Self-cyclisation as a general and efficient platform for peptide and protein macrocyclisation.Communications chemistry · 2023Article
- Chemo-Enzymatic Synthesis of Non-ribosomal Macrolactams by a Penicillin-Binding Protein-Type Thioesterase.Methods in molecular biology (Clifton, N.J.) · 2023Article
- Using the Cyclotide Scaffold for Targeting Biomolecular Interactions in Drug Development.Molecules (Basel, Switzerland) · 2022Review
- Amide Bonds Meet Flow Chemistry: A Journey into Methodologies and Sustainable Evolution.ChemSusChem · 2022Review
- Yeast-based bioproduction of disulfide-rich peptides and their cyclization via asparaginyl endopeptidases.Nature protocols · 2021Article
- Methodologies for Backbone Macrocyclic Peptide Synthesis Compatible With Screening Technologies.Frontiers in chemistry · 2020Review
- The Potential of the Cyclotide Scaffold for Drug Development.Biomedicines · 2019Review
- Synthesis of Constrained Tetracyclic Peptides by Consecutive CEPS, CLIPS, and Oxime Ligation.Organic letters · 2019Article
- Natural Occurring and Engineered Enzymes for Peptide Ligation and Cyclization.Frontiers in chemistry · 2019Review
- Immobilization of Staphylococcus aureus Sortase A on Chitosan Particles and Its Applications in Peptide-to-Peptide Ligation and Peptide Cyclization.Molecules (Basel, Switzerland) · 2018Article
- Cyclotides, a versatile ultrastable micro-protein scaffold for biotechnological applications.Bioorganic & medicinal chemistry letters · 2017Review
- Sortase-mediated chemical protein synthesis reveals the bidentate binding of bisphosphorylated p62 with K63 diubiquitin.Chemical science · 2017Article
Corrections and comments
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Authors and funding
10 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Disulfide-rich cyclic peptides have generated great interest in the development of peptide-based therapeutics due to their exceptional stability toward chemical, enzymatic, or thermal attack. In particular, they have been used as scaffolds onto which bioactive epitopes can be grafted to take advantage of the favorable biophysical properties of disulfide-rich cyclic peptides. To date, the most commonly used method for the head-to-tail cyclization of peptides has been native chemical ligation. In recent years, however, enzyme-mediated cyclization has become a promising new technology due to its efficiency, safety, and cost-effectiveness. Sortase A (SrtA) is a bacterial enzyme with transpeptidase activity. It recognizes a C-terminal penta-amino acid motif, LPXTG, and cleaves the amide bond between Thr and Gly to form a thioacyl-linked intermediate. This intermediate undergoes nucleophilic attack by an N-terminal poly-Gly sequence to form an amide bond between the Thr and N-terminal Gly. Here, we demonstrate that sortase A can successfully be used to cyclize a variety of small disulfide-rich peptides, including the cyclotide kalata B1, α-conotoxin Vc1.1, and sunflower trypsin inhibitor 1. These peptides range in size from 14 to 29 amino acids and contain three, two, or one disulfide bond, respectively, within their head-to-tail cyclic backbones. Our findings provide proof of concept for the potential broad applicability of enzymatic cyclization of disulfide-rich peptides with therapeutic potential.
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Registered trials
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.