ArticleJournal of the American Chemical Society2018
Scalable Access to Arylomycins via C-H Functionalization Logic.
Article in Journal of the American Chemical Society, 2018. 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.
- Stereodivergent total synthesis of C5/C6-oxygenated angucyclines: stereochemical reassignment and antitumor activities.Chemical science · 2026Article
- Reprogramming RiPP scaffolds through skeletal editing unlocks chemical space.Chemical science · 2026Article
- Unified Access to Biaryl-Bridged Linkages Unlocks Structural Diversification of Noncanonical Cyclic Peptides.Journal of the American Chemical Society · 2026Article
- Biosynthesis of Macrocyclic Peptides with C-Terminal β-Amino-α-keto Acid Groups by Three Different Metalloenzymes.ACS central science · 2024Article
- Non-symmetric stapling of native peptides.Nature reviews. Chemistry · 2024Review
- Recent advances in oxidative phenol coupling for the total synthesis of natural products.Natural product reports · 2024Review
- Biosynthesis of macrocyclic peptides with C-terminal β-amino-α-keto acid groups by three different metalloenzymes.bioRxiv : the preprint server for biology · 2024Article
- Synthetic ramoplanin analogues are accessible by effective incorporation of arylglycines in solid-phase peptide synthesis.Chemical science · 2023Article
- In vitro maturation of NiSOD reveals a role for cytoplasmic histidine in processing and metalation.Metallomics : integrated biometal science · 2023Article
- Stretching Peptides to Generate Small Molecule β-Strand Mimics.ACS central science · 2023Article
- Visible-Light-Induced Oxidative Coupling of Phenols and Alkenylphenols with a Recyclable, Solid Photocatalyst.Organic letters · 2023Article
- Atroposelective Total Synthesis of Darobactin A.Journal of the American Chemical Society · 2022Article
- Umpolung strategies for the functionalization of peptides and proteins.Chemical science · 2022Review
- Carrier Protein-Free Enzymatic Biaryl Coupling in Arylomycin A2 Assembly and Structure of the Cytochrome P450 AryC.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Organometallic AlaChem catalysis · 2021Article
- Emerging peptide antibiotics with therapeutic potential.Medicine in drug discovery · 2021Review
- Rhodium(iii) catalyzed olefination and deuteration of tetrahydrocarbazole.RSC advances · 2021Article
- Ideality in Context: Motivations for Total Synthesis.Accounts of chemical research · 2021Article
- Oxidative Photocatalytic Homo- and Cross-Coupling of Phenols: Nonenzymatic, Catalytic Method for Coupling Tyrosine.ACS catalysis · 2020Article
- Unconventional Macrocyclizations in Natural Product Synthesis.ACS central science · 2020Review
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
Arylomycins are a promising class of "latent" antibacterial natural products currently in preclinical development. Access to analogues within this family has previously required a lengthy route involving multiple functional group manipulations that is costly and time-intensive on scale. This study presents a simplified route predicated on simple C-H functionalization logic that is enabled by a Cu-mediated oxidative phenol coupling that mimics the putative biosynthesis. This operationally simple macrocyclization is the largest of its kind and can be easily performed on gram scale. The application of this new route to a formal synthesis of the natural product and a collection of new analogues along with their biological evaluation is also reported.
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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.