Yike Zou

Contact information
email: zou1@llnl.gov

 

 

 

Education/Experience

PhD, Synthetic Organic Chemistry, University of Pennsylvania, Philadelphia, PA, 2012-2017

Postdoc, Computational Chemistry, UCLA, Los Angeles, CA, 2018-2022

 

Research

I am a molecular designer bridging experimental and computational chemistry to design valuable small organic molecules and large biomolecules. I have a long-standing research interest in the chemistry and biology of bioactive compounds -- both natural products and synthetic molecules. I have research experience in natural product discovery, total synthesis, biosynthesis, and protein design. Currently I am interested in applying my experience to the computational design of new drugs.

 

Publications

Gao, L.; Zou, Y.; Liu, X.; Yang, J.; Du, X.; Wang, J.; Yu, X.; Fan, J.; Jiang, M.; Li, Y.; Houk, K. N.; Lei, X., Nature Catalysis, 2021 (ASAP), “Enzymatic control of endo- and exo-stereoselective Diels–Alder reactions with broad substrate scope” doi.org/10.1038/s41929-021-00717-8

Chen Zhang, Hao Zuo, Ga Young Lee, Yike Zou, Qiu-Di Dang, K. N. Houk*, Dawen Niu*, Nature Chemistry, 2021, (ASAP), “Radical Activation of Glycosyl Donors Enables Development of Mild and Stereoconvergent 1,2-cis-Glycosylation”

Zou, Y.*; Houk, K. N.*, J. Am. Chem. Soc. 2021, 143 (30), 11734-11740. “Mechanisms and Dynamics of Synthetic and Biosynthetic Formation of Delitschiapyrones: Solvent Control of Ambimodal Periselectivity” doi.org/10.1021/jacs.1c05293

Deng, Y.#; Zou, Y. #; Yang, C.-P. H.; Houk, K. N.; Smith, A. B., J. Org. Chem. 2021, 86 (19), 13583-13597. “Total Syntheses of (+)-Peniciketals A-B and (−)-Diocollettines A Exploiting a Photoisomerization/Cyclization Union Protocol” doi.org/10.1021/acs.joc.1c01635

Wan, L.-Q.#; Zhang, X.#; Zou, Y.#; Shi, R.; Cao, J.-G.; Xu, S.-Y.; Deng, L.-F.; Zhou, L.; Gong, Y.; Shu, X.; Lee, G. Y.; Ren, H.; Dai, L.; Qi, S.; Houk, K. N.; Niu, D., J. Am. Chem. Soc. 2021, 143 (31), 11919-11926. “Nonenzymatic Stereoselective S-Glycosylation of Polypeptides and Proteins” doi.org/10.1021/jacs.1c05156

Anthony, S. M. #; Tona, V. #; Zou, Y. #; Morrill, L. A.; Billingsley, J. M.; Lim, M.; Tang, Y.; Houk, K. N.; Garg, N. K., J. Am. Chem. Soc. 2021, 143, 7471-7479. “Total Synthesis of (−)-Strictosidine and Interception of Aryne Natural Product Derivatives “Strictosidyne” and “Strictosamidyne” doi.org/10.1021/jacs.1c02004

Basler, S.; Studer, S.; Zou, Y.; Mori, T.; Ota, Y.; Camus, A.; Bunzel, A.; Helgeson, R.; Houk, K.  N.; Jiménez-Osés, G.; Hilvert, D. Nature Chemistry 2021, 13, 231-235. “Efficient Lewis acid catalysis of an abiological reaction in a de novo protein scaffold” doi.org/10.1038/s41557-020-00628-4.  (Highlighted on UCLA News Report and C&EN news)

Zou, Y.; Yang, S.; Sanders, J. N.; Li, W.; Yu, P.; Wang, H.; Tang, Z.; Liu, W.; Houk, K.N. J. Am. Chem. Soc. 2020, 142, 20232-20239. “Computational Investigation of the Mechanism of Diels–Alderase PyrI4” doi.org/10.1021/jacs.0c10813

Yang, F.; Gao, Y.; Chang Y.; Zou, Y.; Houk, K. N.; Lu, J.; He, J.; Tang, W.; Liao, H.; Han, H.; Lin, H. J. Nat. Prod., 2020, 83, 3758-3763. “Aromatic ring substituted aaptamine analogues as potential cytotoxic agents against extranodal natural killer/T-cell lymphoma” doi.org/10.1021/acs.jnatprod.0c00769

Liu, L.; Zou, Y.; Bhattacharya, A.; Zhang, D.; Lang, S. Q.; Houk, K. N.; Devaraj, N. K. Nature Chemistry 2020, 12, 1029-1034. “Enzyme-free synthesis of natural phospholipids in water” doi.org/10.1038/s41557-020-00559-0

Zou, Y.; Wong, J.; Houk, K. N. J. Am. Chem. Soc. 2020, 142, 38, 16403–16408. “Computational exploration of a redox-neutral organocatalytic Mitsunobu reaction” doi.org/10.1021/jacs.0c07487

Li, H.; Liang, Y.-R.; Chen, S.-X.; Wang, W.-X.; Zou, Y.; Nuryyeva, S.; Houk, K. N.; Xiong, J.; Hu, J.-F. J. Nat. Prod. 2020, 83, 2129-2144. “Amentotaxins C–V, structurally diverse diterpenoids from the leaves and twigs of the vulnerable conifer Amentotaxus argotaenia and their cytotoxic effects” doi.org/10.1021/acs.jnatprod.0c00064

Low, Z. J. #; Ma, G.-L. #; Tran, H. T. #; Zou, Y. #; Xiong, J.; Pang, L.; Nuryyeva, S.; Ye, H.; Hu, J.-F.; Houk, K. N.; Liang, Z.-X. J. Am. Chem. Soc. 2020, 142, 1673-1679. “Sungei­dines from a non-canonical enediyne biosynthetic pathway” doi.org/10.1021/jacs.9b10086

Liu, L.; Zou, Y.; Bhattacharya, A.; Zhang, D.; Lang, S. Q.; Houk, K. N.; Devaraj, N. K. bioRxiv 2019, 746156. “Enzyme-free synthesis of natural phospholipids in water” doi.org/10.1101/746156

Zou, Y.; Chen, S.; Houk, K. N. J. Am. Chem. Soc. 2019, 141, 12382-12387. “Origins of selective formation of 5-vinyl-2-methylene furans from oxyallyl/diene (3+2) cycloadditions with Pd(0) catalysis” doi.org/10.1021/jacs.9b05762

Zou, Y.; Xue, X.-S.; Deng, Y.; Smith, A. B.; Houk, K. N. Org. Lett. 2019, 21, 5894-5897. “Factors controlling reactivity in the hydrogen atom transfer and radical addition steps of a radical relay cascade” doi.org/10.1021/acs.orglett.9b02023

Xiong, J.; Meng, W.-J.; Zhang, H.-Y.; Zou, Y.; Wang, W.-X.; Wang, X.-Y.; Yang, Q.-L.; Osman, E. E. A.; Hu, J.-F. Phytochemistry 2019, 162, 183-192. “Lycofargesiines A–F, further lycopodium alkaloids from the club moss Huperzia fargesii” doi.org/10.1016/j.phytochem.2019.03.015

Deng, Y.; Nguyen, M. D.; Zou, Y.; Houk, K. N.; Smith, A. B. Org. Lett. 2019, 21, 1708-1712. “Generation of dithianyl and dioxolanyl radicals using photoredox catalysis: application in the total synthesis of the danshenspiroketallactones via radical relay chemistry” doi.org/10.1021/acs.orglett.9b00271

Zou, Y.; Wang, X.; Sims, J.; Wang, B.; Pandey, P.; Welsh, C. L.; Stone, R. S.; Avery, M. A.; Doerksen, R. J.; Ferreira, D.; Anklin, C.; Valeriote, F. A.; Kelly, M.; Hamann, M. T. J. Am. Chem. Soc. 2019, 141, 4338-4344. “Computationally-assisted discovery and assignment of a highly strained and PANC-1 selective alkaloid from Alaska’s deep ocean” doi.org/10.1021/jacs.8b11403

Tang, Y.; Li, N.; Zou, Y.; Ai, Y.; Ma, G.-L.; Osman, E. E. A.; Xiong, J.; Li, J.; Jin, Z.-X.; Hu, J.-F. Phytochemistry 2019, 160, 25-30. “LC-MS guided isolation and dereplication of lycopodium alkaloids from Lycopodium cernuum var. sikkimense of different geographical origins” doi.org/10.1016/j.phytochem.2019.01.006

Zou, Y.; Li, X.; Yang, Y.; Berritt, S.; Melvin, J.; Gonzales, S.; Spafford, M.; Smith, A. B. J. Am. Chem. Soc. 2018, 140, 9502. “Total synthesis of (−)-nodulisporic acids D, C, and B: evolution of a unified synthetic strategy” doi.org/10.1021/jacs.8b04053

Ai, Y.; Kozytska, M. V.; Zou, Y.; Khartulyari, A. S.; Maio, W. A.; Smith, A. B. J. Org. Chem. 2018, 83, 6110. “Total synthesis of the marine phosphomacrolide, (−)-enigmazole A, exploiting multicomponent type I anion relay chemistry (ARC) in conjunction with a late-stage Petasis–Ferrier union/rearrangement” doi.org/10.1021/acs.joc.8b00899

Zou, Y.; Gutierrez, O.; Sader, A. C.; Patel, N. D.; Fandrick, D. R.; Busacca, C. A.; Fandrick, K. R.; Kozlowski, M.; Senanayake, C. H. Org. Lett. 2017, 19, 6064. “A computational investigation of the ligand-controlled Cu-catalyzed site-selective propargylation and allenylation of carbonyl compounds” doi.org/10.1021/acs.orglett.7b02845

Zou, Y.; Smith, A. B. J Antibiot 2017, 30, 94. “Total synthesis of architecturally complex indole terpenoids: strategic and tactical evolution” doi.org/10.1038/ja.2017.94 – Special issue in honor of Professor K. C. Nicolaou

Tang, Y.; Xiong, J.; Zou, Y.; Wang, W.; Huang, C.; Zhang, H.-Y.; Hu, J.-F. Phytochemistry 2017, 143, 1. “Annotinolide F and lycoannotines A–I, further lycopodium alkaloids from Lycopodium annotinumdoi.org/10.1016/j.phytochem.2017.07.003

Hu, C.-L.; Xiong, J.; Gao, L.-X.; Li, J.; Zeng, H.; Zou, Y.; Hu, J.-F. RSC Advances 2016, 6, 60467. “Diterpenoids from the shed trunk barks of the endangered plant Pinus dabeshanensis and their PTP1B inhibitory effects” doi.org/10.1039/C6RA08986K

Wang, L.-J.; Xiong, J.; Zou, Y.; Mei, Q.-B.; Wang, W.-X.; Hu, J.-F. Phytochemistry Letters 2016, 18, 202. “Sesquiterpenoids from the Chinese endangered plant Manglietia aromaticadoi.org/10.1016/j.phytol.2016.10.018

Tang, Y.; Xiong, J.; Zou, Y.; Zhang, H.-Y.; Hu, J.-F. Phytochemistry 2016, 131, 130. “Palhicerines A-F, lycopodium alkaloids from the club moss Palhinhaea cernua” doi.org/10.1016/j.phytochem.2016.08.010

Xiong, J.; Hong, Z.-L.; Xu, P.; Zou, Y.; Yu, S.-B.; Yang, G.-X.; Hu, J.-F. Organic & Biomolecular Chemistry 2016, 14, 4678. “ent-Abietane diterpenoids with anti-neuroinflamm­atory activity from the rare Chloranthaceae plant Chloranthus ol dhamiidoi.org/10.1039/C6OB00731G

Tang, Y.; Xiong, J.; Zou, Y.; Nay, B.; Wang, L.-J.; Hu, J.-F. Chin. Chem. Lett. 2016, 27, 969. “Palcernuine, the first [5/6/6/6]-cernuane-type alkaloid from Palhinhaea cernua f. sikkim­ensisdoi.org/10.1016/j.cclet.2016.02.014

Xiong, L.; Zhou, Q.-M.; Zou, Y.; Chen, M.-H.; Guo, L.; Hu, G.-Y.; Liu, Z.-H.; Peng, C. Org. Lett. 2015. “Leonuketal, a spiroketal diterpenoid from Leonurus japonicus”  doi.org/10.1021/acs.orglett.5b03227

Ai, Y.; Kozytska, M. V.; Zou, Y.; Khartulyari, A. S.; Smith, A. B. J. Am. Chem. Soc. 2015, 137, 15426. “Total synthesis of (−)-enigmazole A” doi.org/10.1021/jacs.5b11540 (Selected by Synfacts, Carreira, E. M.; Westphal, M. Synfacts 2016, 12, 0117. “Synthesis of (–)-Enigmazole Adoi.org/10.1055/s-0035-1561117; included in the book Organophosphorus Chemistry, Oxford University Press, 2017, authored by Professor John C. Tebby)

Zou, Y.; Melvin, J. E.; Gonzales, S. S.; Spafford, M. J.; Smith, A. B. J. Am. Chem. Soc. 2015, 137, 7095. “Total synthesis of (−)-nodulisporic acid D” doi.org/10.1021/jacs.5b04728. (Selected by D. F. Taber, Org. Chem. Highlights 2015, September 7; selected by Synfacts, Carreira, E. M.; Fischer, S. Synfacts 2015, 11, 0796. “Synthesis of (–)-Nodulisporic Acid Ddoi.org/10.1055/s-0034-1381168; included in the book “Organic Synthesis: State of the Art, 2013-2015”)

He, Y.-C.; Zou, Y.; Peng, C.; Liu, J.-L.; He, C.-J.; Guo, L.; Xie, X.-F.; Xiong, L. Fitoterapia 2015, 100, 7. “Penthorin A and B, two unusual 2,4′-epoxy-8,5′-neolignans from Penthorum chinesedoi.org/10.1016/j.fitote.2014.11.006

Yang, F.#; Zou, Y. #; Wang, R.-P.; Hamann, M.; Zhang, H.-J.; Jiao, W.-H.; Han, B.-N.; Song, S.-J.; Lin, H.-W. Marine Drugs 2014, 12, 4399. “Relative and absolute stereochemistry of diacarperoxides: antimalarial norditerpene endoperoxides from marine sponge Diacarnus megaspinorhabdosadoi.org/10.3390/md12084399

Albadry, M.; Zou, Y.; Takahashi, Y.; Waters, A.; Hossein, M.; Tomioka, T.; Hamann, M. T. Planta Med 2013, 79, PT2. “Progress toward the total synthesis of the marine natural product karlotoxin 5” doi.org/10.1055/s-0033-1348824

Oh, J.; Bowling, J. J.; Zou, Y.; Chittiboyina, A. G.; Doerksen, R. J.; Ferreira, D.; Leininger, T. D.; Hamann, M. T. Biochimica et Biophysica Acta (BBA) - General Subjects 2013, 1830, 4229. “Configurational assignments of conformationally restricted bis-monoterpene hydroquinones: utility in exploration of endangered plants” doi.org/10.1016/j.bbagen.2013.04.029

Zou, Y.; Hamann, M. T. Org. Lett. 2013, 15, 1516. “Atkamine: a new pyrroloiminoquinone scaffold from the cold water Aleutian Islands Latrunculia sponge” doi.org/10.1021/ol400294v

(Selected by ACS cross-journal organic chemistry virtual issue “All Natural – the Renaissan­ce of Natural Products Chemistry” doi.org/10.1021/jo501288m)

Belofsky, G.; Kolaczkowski, M.; Adams, E.; Schreiber, J.; Eisenberg, V.; Coleman, C. M.; Zou, Y.; Ferreira, D. J. Nat. Prod. 2013, 76, 915. “Fungal ABC transporter-associated activity of isoflavonoids from the root extract of Dalea formosa” doi.org/10.1021/np4000763

Wang, W.-X.; Zhu, J.-J.; Zou, Y.; Hong, Z.-L.; Liu, S.-T.; Li, M.; Huang, Y.; Xiong, J.; Zhao, Y.; Yang, G.-X.; Xia, G.; Hu, J.-F. Tetrahedron Lett. 2013, 54, 2549. “Trichotomone, a new cytotoxic dimeric abietane-derived diterpene from Clerodendrum trichotomumdoi.org/10.1016/j.tetlet.2013.03.048

Wahba, A. E.; Fromentin, Y.; Zou, Y.; Hamann, M. T. Tetrahedron Lett. 2012, 53, 6329. “Acantholactone, a new manzamine related alkaloid with an unprecedented d-lactone and e-lactam ring system” doi.org/10.1016/j.tetlet.2012.08.140

Xu, Y.-J.; Foubert, K.; Dhooghe, L.; Lemière, F.; Maregesi, S.; Coleman, C. M.; Zou, Y.; Ferreira, D.; Apers, S.; Pieters, L. Phytochemistry 2012, 79, 121. “Rapid isolation and identification of minor natural products by LC–MS, LC–SPE–NMR and ECD: isoflavanones, biflavanones and bisdihydrocoumarins from Ormocarpum kirkii” doi.org/10.1016/j.phytochem.2012.04.004

Yang, F.; Hamann, M. T.; Zou, Y.; Zhang, M.-Y.; Gong, X.-B.; Xiao, J.-R.; Chen, W.-S.; Lin, H.-W. J. Nat. Prod. 2012, 75, 774. “Antimicrobial metabolites from the paracel islands sponge Agelas mauritianadoi.org/10.1021/np2009016

Wang, J.; Zhai, W.-Z.; Zou, Y.; Zhu, J.-J.; Xiong, J.; Zhao, Y.; Yang, G.-X.; Fan, H.; Hamann, M. T.; Xia, G.; Hu, J.-F. Tetrahedron Lett. 2012, 53, 2654. “Eucalyptals D and E, new cytotoxic phloroglucinols from the fruits of Eucalyptus globulus and assignment of absolute configuration” doi.org/10.1016/j.tetlet.2012.03.073