ArticleJournal of the American Chemical Society2008
Analysis of the cryptophycin P450 epoxidase reveals substrate tolerance and cooperativity.
Article in Journal of the American Chemical Society, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Discovery of Peptide-Based Tubulin Inhibitors Through Structure-Guided Design.Pharmaceutics · 2026Article
- Macrocyclizing-thioesterases in bacterial non-ribosomal peptide biosynthesis.Journal of natural medicines · 2025Review
- Cytochrome P450s in algae: Bioactive natural product biosynthesis and light-driven bioproduction.Acta pharmaceutica Sinica. B · 2022Review
- Review
- Biosynthesis of depsipeptides, or Depsi: The peptides with varied generations.Protein science : a publication of the Protein Society · 2020Review
- Mechanism-Guided Design and Discovery of Efficient Cytochrome P450-Derived C-H Amination Biocatalysts.Journal of the American Chemical Society · 2020Article
- A Versatile Chemoenzymatic Synthesis for the Discovery of Potent Cryptophycin Analogs.ACS chemical biology · 2020Article
- Engineering cytochrome P450 enzyme systems for biomedical and biotechnological applications.The Journal of biological chemistry · 2020Review
- A distributive peptide cyclase processes multiple microviridin core peptides within a single polypeptide substrate.Nature communications · 2018Article
- Biochemical and Structural Characterization of MycCI, a Versatile P450 Biocatalyst from the Mycinamicin Biosynthetic Pathway.ACS chemical biology · 2016Article
- Polyketide intermediate mimics as probes for revealing cryptic stereochemistry of ketoreductase domains.ACS chemical biology · 2014Article
- Efficient, divergent synthesis of cryptophycin unit A analogues.Chemical communications (Cambridge, England) · 2012Article
- Chemodiversity in freshwater and terrestrial cyanobacteria - a source for drug discovery.Current drug targets · 2011Review
- Chemoenzymatic synthesis of cryptophycin anticancer agents by an ester bond-forming non-ribosomal peptide synthetase module.Journal of the American Chemical Society · 2011Article
- Natural product biosyntheses in cyanobacteria: A treasure trove of unique enzymes.Beilstein journal of organic chemistry · 2011Article
- Frontiers and opportunities in chemoenzymatic synthesis.The Journal of organic chemistry · 2010Review
- Cooperative properties of cytochromes P450.Pharmacology & therapeutics · 2009Review
- Functional analysis of an aspartate-based epoxidation catalyst with amide-to-alkene peptidomimetic catalyst analogues.Angewandte Chemie (International ed. in English) · 2008Article
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Authors and funding
4 authors.
Funding
Abstract
Cryptophycins are potent anticancer agents isolated from Nostoc sp. ATCC 53789 and Nostoc sp. GSV 224. The most potent natural cryptophycin analogues retain a beta-epoxide at the C2'-C3' position of the molecule. A P450 epoxidase encoded by c rpE recently identified from the cryptophycin gene cluster was shown to install this key functional group into cryptophycin-4 (Cr-4) to produce cryptophycin-2 (Cr-2) in a regio- and stereospecific manner. Here we report a detailed characterization of the CrpE epoxidase using an engineered maltose binding protein (MBP)-CrpE fusion. The substrate tolerance of the CrpE polypeptide was investigated with a series of structurally related cryptophycin analogues generated by chemoenzymatic synthesis. The enzyme specifically installed a beta-epoxide between C2' and C3' of cyclic cryptophycin analogues. The kcat/Km values of the enzyme were determined to provide further insights into the P450 epoxidase catalytic efficiency affected by substrate structural variation. Finally, binding analysis revealed cooperativity of MBP-CrpE toward natural and unnatural desepoxy cryptophycin substrates.
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