Herzon, Seth - Yale University - Department of Chemistry

个人简介

Education B.S. Temple University, 2002 Ph.D. Harvard University, 2006 Postdoctoral Fellow, University of Illinois, 2006-2008 Honors Petroleum Research Fund Undergraduate Research Fellowship, 2001-2002 The F. Albert Cotton and Al Tulinsky Prize, 2002 National Science Foundation Graduate Research Fellowship, 2003 Harvard University Certificate of Distinction in Teaching, 2003 National Institutes of Health Postdoctoral Fellowship, 2006 Lilly New Faculty Award, 2008 Searle Scholar Award, 2010 American Cancer Society Research Scholar Award, 2010 Synthesis/Synlett Journal Award, 2011 Packard Fellowship in Science and Engineering, 2011 NSF CAREER Award, 2012 Alfred P. Sloan Fellowship, 2012 Cottrell Scholar Award of the Research Corporation for Scientific Advancement, 2012 Camille Dreyfus Teacher-Scholar Award, 2012 Boehringer Ingelheim Pharmaceuticals Creative Synthetic Organic Chemistry Award, 2012 Amgen Young Investigator Award, 2013 Eli Lilly Grantee Award, 2013 Arthur C. Cope Scholar Award, 2014 Natural Products Reports Emerging Investigator Lectureship, 2015 Novartis Chemistry Lectureship, 2016 Defense Science Study Group, Sponsored by the Institute for Defense Analyses, 2018-2019 Elias J. Corey Award for Outstanding Original Contribution in Organic Synthesis by a Young Investigator, 2018 Tetrahedron Young Investigator Award (Organic Synthesis), 2018

研究领域

Emergence is the phenomenon by which novel properties arise from interactions of simpler fragments which lack that property at a given level of hierarchical complexity. In chemical systems such as polyfunctional natural products, emergent properties are difficult if not impossible to predict, even when very detailed information about the interacting fragments is available. Efforts to analyze natural products without considering their emergent phenomena typically fail as an approach to identifying the most interesting functional features of these molecules. Therefore, our laboratory is working to formalize a study of emergence in bioactive natural products, with the ultimate goal of connecting the modular, evolved chemical reactivity within a natural product with cellular phenotype. Studies of this nature enrich our understanding of structure, bonding and reactivity in complex settings, motivate advances in synthetic strategy and methodology, and provide a blueprint for the creation of novel molecules with desired, complex properties, with implications for human health.

近期论文

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Dougherty MW, Valdés-Mas R, Wernke KM, Gharaibeh RZ, Yang Y, Brant JO, Riva A, Muehlbauer M, Elinav E, Puschhof J, Herzon SB, Jobin C. The microbial genotoxin colibactin exacerbates mismatch repair mutations in colorectal tumors. Neoplasia. 2023 Sep;43:100918. doi: 10.1016/j.neo.2023.100918. Epub 2023 Jul 25. PubMed PMID: 37499275; PubMed Central PMCID: PMC10413156. Xu Z, Li X, Rose JA, Herzon SB. Finding activity through rigidity: syntheses of natural products containing tricyclic bridgehead carbon centers. Nat Prod Rep. 2023 Aug 16;40(8):1393-1431. doi: 10.1039/d3np00008g. Review. PubMed PMID: 37140079; PubMed Central PMCID: PMC10472132. DiBello M, Healy AR, Nikolayevskiy H, Xu Z, Herzon SB. Structure Elucidation of Secondary Metabolites: Current Frontiers and Lingering Pitfalls. Acc Chem Res. 2023 Jun 20;56(12):1656-1668. doi: 10.1021/acs.accounts.3c00183. Epub 2023 May 23. PubMed PMID: 37220079; PubMed Central PMCID: PMC10468810. Frischling MC, Herzon SB. On the Abundance and Stability of Diazo-Containing Secondary Metabolites: Enantioselective Synthesis of (-)-Nenestatin A. Org Lett. 2023 May 26;25(20):3723-3727. doi: 10.1021/acs.orglett.3c01175. Epub 2023 May 12. PubMed PMID: 37172275; PubMed Central PMCID: PMC10468809. Hsu IT, Herzon SB. Fragment Coupling Approach to Diaporthein B. J Org Chem. 2023 Feb 17;88(4):2221-2244. doi: 10.1021/acs.joc.2c02655. Epub 2023 Feb 3. PubMed PMID: 36737056. Goethe O, DiBello M, Herzon SB. Total synthesis of structurally diverse pleuromutilin antibiotics. Nat Chem. 2022 Nov;14(11):1270-1277. doi: 10.1038/s41557-022-01027-7. Epub 2022 Sep 26. PubMed PMID: 36163267; PubMed Central PMCID: PMC9633427. Xu Z, DiBello M, Wang Z, Rose JA, Chen L, Li X, Herzon SB. Stereocontrolled Synthesis of the Fully Glycosylated Monomeric Unit of Lomaiviticin A. J Am Chem Soc. 2022 Sep 7;144(35):16199-16205. doi: 10.1021/jacs.2c07631. Epub 2022 Aug 23. PubMed PMID: 35998350; PubMed Central PMCID: PMC9502020. Hoang KM, Zheng X, Herzon SB. Synthesis of 2-Deoxyglycosides Bearing Free Hydroxyl Substituents on the Glycosyl Donor. J Org Chem. 2022 Aug 19;87(16):10768-10790. doi: 10.1021/acs.joc.2c01003. Epub 2022 Aug 3. PubMed PMID: 35921523; PubMed Central PMCID: PMC9511991. Lin K, Gueble SE, Sundaram RK, Huseman ED, Bindra RS, Herzon SB. Mechanism-based design of agents that selectively target drug-resistant glioma. Science. 2022 Jul 29;377(6605):502-511. doi: 10.1126/science.abn7570. Epub 2022 Jul 28. PubMed PMID: 35901163; PubMed Central PMCID: PMC9502022. Patel JR, Oh J, Wang S, Crawford JM, Isaacs FJ. Cross-kingdom expression of synthetic genetic elements promotes discovery of metabolites in the human microbiome. Cell. 2022 Apr 28;185(9):1487-1505.e14. doi: 10.1016/j.cell.2022.03.008. Epub 2022 Apr 1. PubMed PMID: 35366417; PubMed Central PMCID: PMC10619838. Gatsios A, Kim CS, Crawford JM. Escherichia coli small molecule metabolism at the host-microorganism interface. Nat Chem Biol. 2021 Oct;17(10):1016-1026. doi: 10.1038/s41589-021-00807-5. Epub 2021 Sep 22. Review. PubMed PMID: 34552219; PubMed Central PMCID: PMC8675634. Kim CS, Turocy T, Moon G, Shine EE, Crawford JM. Escherichia coli-Derived γ-Lactams and Structurally Related Metabolites Are Produced at the Intersection of Colibactin and Fatty Acid Biosynthesis. Org Lett. 2021 Sep 3;23(17):6895-6899. doi: 10.1021/acs.orglett.1c02461. Epub 2021 Aug 18. PubMed PMID: 34406772; PubMed Central PMCID: PMC10577019. Tirla A, Wernke KM, Herzon SB. On the Stability and Spectroscopic Properties of 5-Hydroxyoxazole-4-carboxylic Acid Derivatives. Org Lett. 2021 Jul 16;23(14):5457-5460. doi: 10.1021/acs.orglett.1c01796. Epub 2021 Jun 28. PubMed PMID: 34180681; PubMed Central PMCID: PMC8294165. Kim LJ, Xue M, Li X, Xu Z, Paulson E, Mercado B, Nelson HM, Herzon SB. Structure Revision of the Lomaiviticins. J Am Chem Soc. 2021 May 5;143(17):6578-6585. doi: 10.1021/jacs.1c01729. Epub 2021 Apr 26. PubMed PMID: 33900077; PubMed Central PMCID: PMC8935351. Hoang KM, Lees NR, Herzon SB. General Method for the Synthesis of α- or β-Deoxyaminoglycosides Bearing Basic Nitrogen. J Am Chem Soc. 2021 Feb 24;143(7):2777-2783. doi: 10.1021/jacs.0c11262. Epub 2021 Feb 8. PubMed PMID: 33555855; PubMed Central PMCID: PMC7935422. Hsu IT, Tomanik M, Herzon SB. Metric-Based Analysis of Convergence in Complex Molecule Synthesis. Acc Chem Res. 2021 Feb 16;54(4):903-916. doi: 10.1021/acs.accounts.0c00817. Epub 2021 Feb 1. PubMed PMID: 33523640. Kaneko M, Li Z, Burk M, Colis L, Herzon SB. Synthesis and Biological Evaluation of (2S,2'S)-Lomaiviticin A. J Am Chem Soc. 2021 Jan 20;143(2):1126-1132. doi: 10.1021/jacs.0c11960. Epub 2021 Jan 7. PubMed PMID: 33410680; PubMed Central PMCID: PMC8174553. Tomanik M, Xu Z, Herzon SB. Enantioselective Synthesis of Euonyminol. J Am Chem Soc. 2021 Jan 20;143(2):699-704. doi: 10.1021/jacs.0c12998. Epub 2021 Jan 7. PubMed PMID: 33410701. Tomanik M, Hsu IT, Herzon SB. Fragment Coupling Reactions in Total Synthesis That Form Carbon-Carbon Bonds via Carbanionic or Free Radical Intermediates. Angew Chem Int Ed Engl. 2021 Jan 18;60(3):1116-1150. doi: 10.1002/anie.201913645. Epub 2020 Sep 24. Review. PubMed PMID: 31869476. Williams PC, Wernke KM, Tirla A, Herzon SB. Employing chemical synthesis to study the structure and function of colibactin, a "dark matter" metabolite. Nat Prod Rep. 2020 Nov 18;37(11):1532-1548. doi: 10.1039/d0np00072h. Review. PubMed PMID: 33174565; PubMed Central PMCID: PMC7700718. Herzon SB. Macrocyclic colibactins. Nat Chem. 2020 Nov;12(11):1005-1006. doi: 10.1038/s41557-020-00551-8. Epub 2020 Sep 21. PubMed PMID: 32958888; PubMed Central PMCID: PMC7935421. Wernke KM, Xue M, Tirla A, Kim CS, Crawford JM, Herzon SB. Structure and bioactivity of colibactin. Bioorg Med Chem Lett. 2020 Aug 1;30(15):127280. doi: 10.1016/j.bmcl.2020.127280. Epub 2020 May 23. Review. PubMed PMID: 32527463; PubMed Central PMCID: PMC7309967. Tomanik M, Economou C, Frischling MC, Xue M, Marks VA, Mercado BQ, Herzon SB. Development of a Convergent Enantioselective Synthetic Route to (-)-Myrocin G. J Org Chem. 2020 Jul 17;85(14):8952-8989. doi: 10.1021/acs.joc.0c00891. Epub 2020 Jul 2. PubMed PMID: 32615040; PubMed Central PMCID: PMC7520802. Rose JA, Mahapatra S, Li X, Wang C, Chen L, Swick SM, Herzon SB. Synthesis of the bis(cyclohexenone) core of (-)-lomaiviticin A. Chem Sci. 2020 Jul 9;11(28):7462-7467. doi: 10.1039/d0sc02770g. PubMed PMID: 34123029; PubMed Central PMCID: PMC8159427. Herzon SB. New Leads for the Treatment of Multidrug Resistant Mycobacterium tuberculosis. ACS Cent Sci. 2020 Jun 24;6(6):833-835. doi: 10.1021/acscentsci.0c00684. Epub 2020 Jun 12. PubMed PMID: 32607429; PubMed Central PMCID: PMC7318060. Xue M, Wernke KM, Herzon SB. Depurination of Colibactin-Derived Interstrand Cross-Links. Biochemistry. 2020 Feb 25;59(7):892-900. doi: 10.1021/acs.biochem.9b01070. Epub 2020 Feb 13. PubMed PMID: 31977191; PubMed Central PMCID: PMC7521609. Healy AR, Wernke KM, Kim CS, Lees NR, Crawford JM, Herzon SB. Addendum: Synthesis and reactivity of precolibactin 886. Nat Chem. 2019 Dec;11(12):1167. doi: 10.1038/s41557-019-0383-x. PubMed PMID: 31719668; PubMed Central PMCID: PMC7523535. Healy AR, Wernke KM, Kim CS, Lees NR, Crawford JM, Herzon SB. Synthesis and reactivity of precolibactin 886. Nat Chem. 2019 Oct;11(10):890-898. doi: 10.1038/s41557-019-0338-2. Epub 2019 Sep 23. PubMed PMID: 31548676; PubMed Central PMCID: PMC6761996. Xue M, Kim CS, Healy AR, Wernke KM, Wang Z, Frischling MC, Shine EE, Wang W, Herzon SB, Crawford JM. Structure elucidation of colibactin and its DNA cross-links. Science. 2019 Sep 6;365(6457). doi: 10.1126/science.aax2685. Epub 2019 Aug 8. PubMed PMID: 31395743; PubMed Central PMCID: PMC6820679. Goethe O, Heuer A, Ma X, Wang Z, Herzon SB. Antibacterial properties and clinical potential of pleuromutilins. Nat Prod Rep. 2019 Jan 1;36(1):220-247. doi: 10.1039/c8np00042e. Epub 2018 Jul 6. Review. PubMed PMID: 29979463. Shine EE, Xue M, Patel JR, Healy AR, Surovtseva YV, Herzon SB, Crawford JM. Model Colibactins Exhibit Human Cell Genotoxicity in the Absence of Host Bacteria. ACS Chem Biol. 2018 Dec 21;13(12):3286-3293. doi: 10.1021/acschembio.8b00714. Epub 2018 Nov 20. PubMed PMID: 30403848; PubMed Central PMCID: PMC7001666. Economou C, Tomanik M, Herzon SB. Synthesis of Myrocin G, the Putative Active Form of the Myrocin Antitumor Antibiotics. J Am Chem Soc. 2018 Nov 28;140(47):16058-16061. doi: 10.1021/jacs.8b10891. Epub 2018 Nov 16. PubMed PMID: 30415540; PubMed Central PMCID: PMC7001008.