Thiol Probes To Detect Electrophilic Natural Products Based on Their Mechanism of Action

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The anti-inflammatory natural product parthenolide from the medicinal herb Feverfew directly binds to and inhibits IκB kinase

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XPB, a subunit of TFIIH, is a target of the natural product triptolide

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Lactacystin, a novel microbial metabolite, induces neuritogenesis of neuroblastoma cells.

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Andrographolide Attenuates Inflammation by Inhibition of NF-κB Activation through Covalent Modification of Reduced Cysteine 62 of p50

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Stereospecific total synthesis of a "slow reacting substance" of anaphylaxis, leukotriene C-1

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Mechanistic Studies on the Inactivation of the Proteasome by Lactacystin

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Crystal Structures of Salinosporamide A (NPI-0052) and B (NPI-0047) in Complex with the 20S Proteasome Reveal Important Consequences of β-Lactone Ring Opening and a Mechanism for Irreversible Binding

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Crystal Structure of Epoxomicin:20S Proteasome Reveals a Molecular Basis for Selectivity of α‘,β‘-Epoxyketone Proteasome Inhibitors

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Electrophilic natural products and their biological targets

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Diversity and evolution of secondary metabolism in the marine actinomycete genus Salinispora

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Cyclomarins A−C, New Antiinflammatory Cyclic Peptides Produced by a Marine Bacterium (Streptomyces sp.)

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Protein‐Reactive Natural Products

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Mechanistic Studies on the Inactivation of the Proteasome by Lactacystin in Cultured Cells

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Chemical and enzymic syntheses of 5-HPETE, a key biological precursor of slow-reacting substance of anaphylaxis (SRS), and 5-HETE

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The Natural Product Cyclomarin Kills Mycobacterium Tuberculosis by Targeting the ClpC1 Subunit of the Caseinolytic Protease

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Recent advances in the heterologous expression of microbial natural product biosynthetic pathways

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The Guanacastepenes: A Highly Diverse Family of Secondary Metabolites Produced by an Endophytic Fungus

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Nodulisporic Acid A, a Novel and Potent Insecticide from a Nodulisporium Sp. Isolation, Structure Determination, and Chemical Transformations

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An NMR Spectroscopic Method to Identify and Classify Thiol‐Trapping Agents: Revival of Michael Acceptors for Drug Discovery?

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Eponemycin exerts its antitumor effect through the inhibition of proteasome function.

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Methods and options for the heterologous production of complex natural products

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Mechanism of penicillin action: penicillin and substrate bind covalently to the same active site serine in two bacterial D-alanine carboxypeptidases.

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Structural Basis of Mycobacterial Inhibition by Cyclomarin A

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Salinamides A and B: anti-inflammatory depsipeptides from a marine streptomycete

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Studies on the Mechanism of Phosphatidylinositol 3-Kinase Inhibition by Wortmannin and Related Analogs

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Proteasome inhibition by the natural products epoxomicin and dihydroeponemycin: Insights into specificity and potency

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Brasilicardin A. A Novel Tricyclic Metabolite with Potent Immunosuppressive Activity from Actinomycete Nocardia brasiliensis

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Salinamides, Antiinflammatory Depsipeptides from a Marine Streptomycete

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Covalent Modification of a Cysteine Residue in the XPB Subunit of the General Transcription Factor TFIIH Through Single Epoxide Cleavage of the Transcription Inhibitor Triptolide

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Chemoselective probes for metabolite enrichment and profiling

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Salinosporamides D−J from the Marine Actinomycete Salinispora tropica, Bromosalinosporamide, and Thioester Derivatives Are Potent Inhibitors of the 20S Proteasome

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Antiplasmodial Thiostrepton Derivatives: Proteasome Inhibitors with a Dual Mode of Action

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The Molecular Basis of Conjugated Polyyne Biosynthesis in Phytopathogenic Bacteria

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Transcription inhibition by the depsipeptide antibiotic salinamide A

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Thiol Derivatization for LC-MS Identification of Microcystins in Complex Matrices

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Michael Addition of Amines and Thiols to Dehydroalanine Amides: A Remarkable Rate Acceleration in Water

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Isolation and structure of spatol, a potent inhibitor of cell replication from the brown seaweed Spatoglossum schmittii

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Unified Total Synthesis of Pteriatoxins and Their Diastereomers

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Genetic Basis for the Biosynthesis of the Pharmaceutically Important Class of Epoxyketone Proteasome Inhibitors

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Nucleophilic 1,4-Additions for Natural Product Discovery

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Enrichment Tags for Enhanced-Resolution Profiling of the Polar Metabolome

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Irreversible kinase inhibitors gain traction

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Salinamide F, new depsipeptide antibiotic and inhibitor of bacterial RNA polymerase from a marine-derived Streptomyces sp.

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Gift from Nature: Cyclomarin A Kills Mycobacteria and Malaria Parasites by Distinct Modes of Action

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Chemoselective enrichment for natural products discovery

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Tirandalydigin, a novel tetramic acid of the tirandamycin-streptolydigin type. I. Taxonomy of the producing organism, fermentation and biological activity.

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Triptolide binds covalently to a 90 kDa nuclear protein. Role of epoxides in binding and activity

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Chemical assay-guided natural product isolation via solid-supported chemodosimetric fluorescent probe

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Synthesis and Biological Evaluation of Antitumor‐Active Arglabin Derivatives

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Antineoplastic agents. 200. Absolute configuration of the bryostatins

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Subclass‐Specific Labeling of Protein‐Reactive Natural Products with Customized Nucleophilic Probes

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Thiol-catalysed hydrolysis of benzylpenicillin

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Solid‐Phase Enrichment and Analysis of Azide‐Labeled Natural Products: Fishing Downstream of Biochemical Pathways

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Reaction of cryptophycin 52 with thiols

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Side chain substitution reaction of 2-arylsulfinyl and 2-arylsulfonyl intermediates for 1β-methylcarbapenems

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Synthesis of β,β′-Diamino Acids from α-Amino Acid Derived β-Lactams

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Is there a future for andrographolide to be an anti-inflammatory drug? Deciphering its major mechanisms of action

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Biosynthesis and chemical diversity of β-lactone natural products

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Antibiotic drug discovery

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The hidden enzymology of bacterial natural product biosynthesis

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Designing Chimeric Molecules for Drug Discovery by Leveraging Chemical Biology

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Genomic insights into specialized metabolism in the marine actinomycete Salinispora

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The Photochemical Degradation of Bacterial Cell Wall Using Penicillin‐Based Carbon Dots: Weapons Against Multi‐Drug Resistant (MDR) Strains

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Recent developments on microwave-assisted organic synthesis of nitrogen- and oxygen-containing preferred heterocyclic scaffolds

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Connecting metabolome and phenotype: recent advances in functional metabolomics tools for the identification of bioactive natural products

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Targeting Reactive Carbonyls for Identifying Natural Products and Their Biosynthetic Origins

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Nature's Combinatorial Biosynthesis Produces Vatiamides A–F

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Thiol-Based Probe for Electrophilic Natural Products Reveals That Most of the Ammosamides Are Artifacts

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Reactivity-Based Screening for Citrulline-Containing Natural Products Reveals a Family of Bacterial Peptidyl Arginine Deiminases

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Chimeric natural products derived from medermycin and the nature-inspired construction of their polycyclic skeletons

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3-Bromotetrazine: labelling of macromolecules via monosubstituted bifunctional s -tetrazines

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Chemical labeling strategies for small molecule natural product detection and isolation

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Highly Sensitive Labeling Reagents for Scarce Natural Products

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Neolymphostin A Is a Covalent Phosphoinositide 3-Kinase (PI3K)/Mammalian Target of Rapamycin (mTOR) Dual Inhibitor That Employs an Unusual Electrophilic Vinylogous Ester

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Nitrosopyridine Probe To Detect Polyketide Natural Products with Conjugated Alkenes: Discovery of Novodaryamide and Nocarditriene

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Covalent Small Molecule Immunomodulators Targeting the Protease Active Site

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DeltaMS: a tool to track isotopologues in GC- and LC-MS data

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Bioactive natural products from the genus Salinospora: a review

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Bioinspired Nitroalkylation for Selective Protein Modification and Peptide Stapling

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Identification of Isonitrile‐Containing Natural Products in Complex Biological Matrices through Ligation with Chlorooximes

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Enhancing tandem mass spectrometry-based metabolite annotation with online chemical labeling

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The Cyanobacterial “Nutraceutical” Phycocyanobilin Inhibits Cysteine Protease Legumain

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Thiol-trapping natural products under the lens of the cysteamine assay: friends, foes, or simply alternatively reversible ligands?

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Boron NMR as a Method to Screen Natural Product Libraries for B-Containing Compounds

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Identification and Total Synthesis of an Unstable Anticancer Macrolide Presaccharothriolide Z Produced by Saccharothrix sp. A1506

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Reactivity-based screening for natural product discovery

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Andrographolide induce human embryonic stem cell apoptosis by oxidative stress response

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Discovery of Modified Metabolites, Secondary Metabolites, and Xenobiotics by Structure-Oriented LC–MS/MS

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A Diels–Alder probe for discovery of natural products containing furan moieties

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Bioinspired Nitroalkylation for Selective Protein Modification and Peptide Stapling

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Toward the Dark Matter of Natural Products

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Chemical capture of diazo metabolites reveals biosynthetic hydrazone oxidation

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Solid-phase enrichment and analysis of electrophilic natural products

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Targeting pharmacophore with probe‐reactivity‐guided fractionation to precisely identify electrophilic sesquiterpenes and its activity of anti‐TNBC

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Amino-Based Probe for Natural Products with Covalent Binding Ability to Lysine and Mechanism of Action of Medermycin

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Labeling and Characterization of Phenol‐Containing Glycopeptides Using Chemoselective Probes with Isotope Tags

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Nature's Combinatorial Biosynthesis Produces Vatiamides A–F

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Rings of Power: Enzymatic Routes to β-Lactones

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Pharmacophore-probe reaction guided purification to precisely identify electrophilic withanolides from Tubocapsicum anomalum Makino and their anti-TNBC activity

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Discovery of a Human Metabolite That Mimics the Bacterial Quorum-Sensing Autoinducer AI-2

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Behavioral metabolomics: how behavioral data can guide metabolomics research on neuropsychiatric disorders

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Bromine-Based Derivatization of Carboxyl-Containing Metabolites for Liquid Chromatography–Trapped Ion Mobility Spectrometry–Mass Spectrometry

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Pyrazolidinone-based peptidomimetic SARS-CoV-2 Mpro inhibitors

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Chemical Toolbox to Decode the Microbiota Lexicon

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Development of a solid-supported cysteinyl probe for the isolation of electrophiles from plant pollen extracts

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Natural Products from Marine Actinomycete Genus Salinispora Might Inhibit 3CLpro and PLpro Proteins of SARS-CoV-2: An In Silico Evidence

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Chemoselective Tagging to Promote Natural Product Discovery

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A Nucleophilic Chemical Probe Targeting Electrophilic Functional Groups in an Untargeted Way to Explore Cysteine Modulators in Natural Products

Gao, Y., Li, K., Zhang, L., Chen, C., & Bai, C. (2022) · ACS Chemical Biology · doi:10.1021/acschembio.2c00385 · Cited by 2 · see citing works

A Catch‐Release Strategy for the Genomics‐Driven Discovery of Antiproliferative Furan‐Functionalized Peptides

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A Catch‐Release Strategy for the Genomics‐Driven Discovery of Antiproliferative Furan‐Functionalized Peptides

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Streamlined Methods for Profiling Targeted Michael Acceptor Molecules Reveal Natural PTP1B Covalent Inhibitors

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Some Contributions of Organic Chemistry to the Study of the Biosynthesis of Natural Products

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Penicillins

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Mass-tagged aminated probes for rapid discovery of azaphilic natural products in fungal crude extracts

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Mollugin reacts with phenol thiol but not produce modification on cysteine discovered by a phenol thiol probe

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Capturing and releasing cucurbitacins with α, β-unsaturated group from Cucumis melo based on reversibility of thia-Michael addition reaction

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Thiol Reactome Profiling in Plant-Derived Foods and Discovery of an Abundant Insecticidal Natural Product (R)-Dihydromaleimide in Snow Pea (Pisum sativum)

Yuan, M., Chen, X., Yuan, G., Pu, Y., Liang, X., Liang, D., & Wang, L. (2025) · Journal of Agricultural and Food Chemistry · doi:10.1021/acs.jafc.5c05627

Design and synthesis of fluorescent glyco-dots for detection and cell imaging

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Thiol-reactive compound depletion reveals electrophile-dependent and independent anti-inflammatory constituents in Saussurea costus

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BindingDB Entry 50020848: Pyrazolidinone-based peptidomimetic SARS-CoV-2 M

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BindingDB Entry 50003196: Neolymphostin A Is a Covalent Phosphoinositide 3-Kinase (PI3K)/Mammalian Target of Rapamycin (mTOR) Dual Inhibitor That Employs an Unusual Electrophilic Vinylogous Ester.

BindingDB (2020) · UC San Diego · doi:10.7270/q24f1td1

BindingDB Entry 50018635: Covalent Small Molecule Immunomodulators Targeting the Protease Active Site.

BindingDB (2024) · UC San Diego · doi:10.7270/q2t72nnm

Subclass‐Specific Labeling of Protein‐Reactive Natural Products with Customized Nucleophilic Probes

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A Nucleophilic Chemical Probe Targeting Electrophilic Functional Groups in an Untargeted Way to Explore Cysteine Modulators in Natural Products

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Reactivity-guided isolation of marine and bacterial natural products in the genomic age

Castro‐Falcón, G. (2019) · eScholarship (California Digital Library)

Multiplexed Thiol Reactivity Profiling for Target Discovery of Electrophilic Natural Products

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Nucleophilic 1,4-Additions for Natural Product Discovery

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