ArticleNature chemical biology2017
A new strategy for aromatic ring alkylation in cylindrocyclophane biosynthesis.
Article in Nature chemical biology, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 42 papers.
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Who cites it
42 citing papers in PubMed.
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- Oxidative Rearrangement of Indoles Enabled by Promiscuous Cryptic Halogenation with Vanadium-Dependent Haloperoxidases.ACS catalysis · 2026Article
- P450 Enzyme LyoI Performs Hydro-2,2'-Bifuran Oxidation in the Polyether Ionophore Lysocellin.Angewandte Chemie (International ed. in English) · 2025Article
- Biochemical Studies of a Cyanobacterial Halogenase Support the Involvement of a Dimetal Cofactor.Biochemistry · 2025Article
- Chemoenzymatic C,C-Bond Forming Cascades by Cryptic Vanadium Haloperoxidase Catalyzed Bromination.Organic letters · 2025Article
- Structural insights into type III polyketide synthase CylI from cylindrocyclophane biosynthesis.Protein science : a publication of the Protein Society · 2024Article
- Accelerating the discovery of alkyl halide-derived natural products using halide depletion.Nature chemistry · 2024Article
- Recent Developments and Applications of Biocatalytic and Chemoenzymatic Synthesis for the Generation of Diverse Classes of Drugs.Current pharmaceutical biotechnology · 2024Article
- Chemo-enzymatic total synthesis: current approaches toward the integration of chemical and enzymatic transformations.Beilstein journal of organic chemistry · 2024Review
- Review
- Incorporation and modification of fatty acids in cyanobacterial natural products biosynthesis.Chemical communications (Cambridge, England) · 2023Review
- New Nostocyclophanes fromMarine drugs · 2023Article
- Naturally Occurring Organohalogen Compounds-A Comprehensive Review.Progress in the chemistry of organic natural products · 2023Review
- Discovery and Heterologous Expression of Microginins fromACS synthetic biology · 2022Article
- Biocatalytic Friedel-Crafts Reactions.ChemCatChem · 2022Review
- The Transformative Power of Biocatalysis in Convergent Synthesis.Journal of the American Chemical Society · 2022Review
- Discovery of Anticancer Agents of Diverse Natural Origin.Journal of natural products · 2022Article
- Structural basis for an unprecedented enzymatic alkylation in cylindrocyclophane biosynthesis.eLife · 2022Article
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Authors and funding
3 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Alkylation of aromatic rings with alkyl halides is an important transformation in organic synthesis, yet an enzymatic equivalent is unknown. Here, we report that cylindrocyclophane biosynthesis in Cylindrospermum licheniforme ATCC 29412 involves chlorination of an unactivated carbon center by a novel halogenase, followed by a previously uncharacterized enzymatic dimerization reaction featuring sequential, stereospecific alkylations of resorcinol aromatic rings. Discovery of the enzymatic machinery underlying this unique biosynthetic carbon-carbon bond formation has implications for biocatalysis and metabolic engineering.
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