Chi-Sing Lee
  • Education & Experience

    2005 - present        Associate Professor, Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, China

    2003 - 2005            Research Fellow, Department of Biology and Chemistry, City University of Hong Kong, HK
    2001 - 2003            Lecturer, Department of Chemistry, The University of Hong Kong, HK
    1999 - 2001            Postdoctoral Research Chemist, Medicinal Chemistry Division, Pharmacia & Upjohn, USA
    1993 - 1999            Ph.D. in Organic Chemistry, University of Minnesota at Twin Cities, USA
    1989 - 1992            B.Sc. in Applied Physics and Chemistry, Indiana University of Pennsylvania, USA
     
  • Awards & Honors

    2012                    Asian Core Program Lectureship Award (Japan)

    2006 – 2008        Honorary Assistant Professor, Department of Chemistry, The University of Hong Kong, Hong Kong
     
  • Research Fields

    1. Target-driven methodology development for natural product synthesis

    (i) Dual-mode Lewis acid induced cascade cyclization reactions: Dual-mode Lewis acids play an important role in promoting cascade reactions because they serve to activate reactions of both the starting materials as well as intermediates through different types of σ- and π-binding modes. Our strategy is to search for a suitable dual-mode Lewis acid, which can induce an intermolecular or intramolecular cascade cyclization sequence in one-pot leading to formation of polycyclic frameworks bearing multiple functional groups and stereogenic centers. Base on the theoretical and experimental results, we have utilized Zn2+ and In3+ as dual-mode Lewis acid for development of cascade cyclization reactions and successfully demonstrated their utilities in natural product synthesis

    (ii) Biomimetic strategies: Nature is always referred as the most efficient machine for making biologically active molecules, including biopolymers and small biomolecules. Our strategy is to design new methods for synthesis of natural products by chemical means using Nature’s hypothetical or established strategies (biomimetic synthesis).

    Base on the above strategies, we have developed four new types of cascade cyclization reactions and successfully applied to complex natural products, including all members of basiliolides, clavukerin A, platensimycin, platencin, aglycone of dendronobiloside A, teucvidin, yezo’otogirin C and eriocalyxin B.

    2. Developing novel lanthanide-based fluorescence probes for bioimaging

    Base on the cyclen scaffold, we have design and synthesis of a variety of novel luminescent lanthanide complexes as bio-labeling probes for in vitro and in vivo imaging.


     
  • Selected Publications

    1.   Du, G.; Wang, G.; Ma, W.; Yang, Q.; Bao, W.; Liang, X.; Zhu, L.; Lee, C.-S. “Syntheses of Diverse Natural Products via Dual-mode Lewis Acid Induced Cascade Cyclization Reactions” Synlett 2017, Ahead of print. DOI: 10.1055/s-0036-1588777 (Invited Account).

    2.   Liang, X.; Zhou, L.; Min, L.; Ye, W.; Bao, W.; Ma, W.; Yang, Q.; Qiao, F.; Zhang, X.; Lee, C.-S. “Diastereoselective Total Synthesis of (±)-Basiliolide B and (±)-epi-8-Basiliolide B” J. Org. Chem. 2017, 82, 3463.

    3.   Liang, Z.; Tsoi, T.-H.; Chan, C.-F.; Dai, L.; Wu, Y.; Du, G.; Zhu, L.; Lee, C.-S.; Wong, W.-T. Law, G.-L.; Wong, K.-L. “A smart “off–on” gate for the in situ detection of hydrogen sulphide with Cu(II)-assisted europium emission” Chem. Sci. 2016, 7, 2151.

    4.   Du, G.; Bao, W.; Huang, J.; Huang, S.; Yue, H.; Yang, W.; Zhu, L.; Liang, Z.; Lee, C.-S. “Enantioselective Synthesis of the ABC-Tricyclic Core of Phomactin A by a γ-Hydroxylation Strategy” Org. Lett. 2015, 17, 2062.

    5.   Liang, Z.; Chan, C.-F.; Liu, Y.; Wong, W.-T.; Lee, C.-S.; Law, G.-L.; Wong, K.-L. “The effects of the increasing number of the same chromophore on photosensitization of water-soluble cyclen-based europium complexes with potential for biological applications” RSC Adv. 2015, 5, 13347.

    6.   Yang, W.; Cao, J.; Zhang, M.; Lan, R.; Zhu, L.; Du, G.; He, S.; Lee, C.-S. “Systemic Study on the Biogenic Pathways of Yezo’otogirins: Total Synthesis and Antitumor Activities of (±)-Yezo’otogirin C and Its Structural Analogues” J. Org. Chem. 2015, 80, 836-846.

    7.   Min, L.; Zhang, Y.; Liang, X.; Huang, J.; Bao, W.; Lee, C.-S. “A Biomimetic Synthesis of (±)-Basiliolide B” Angew. Chem. Int. Ed. 2014, 53, 11294.

    8.   He, S.; Yang, W.; Zhu, L.; Du, G.; Lee, C.-S. “Bioinspired Total Synthesis of (±)-Yezo’otogirin C” Org. Lett. 2014, 16, 496.

    9.   Li, H.; Chadbourne, F. L.; Lan, R.; Chan, C.-F.; Chan, W.-L.; Law, G.-L.; Lee, C.-S.; Cobb, S. L.; Wong, K.-L. “Real time detection of cell cycle regulator cyclin A on living tumor cells with europium emission” Dalton Trans. 2013, 13495.

    10.  Zhu, L.; Zhou, C.; Yang, W.; He, S.; Cheng, G.-J.; Zhang, X.; Lee, C.-S. “Formal Syntheses of (±)-Platensimycin and (±)-Platencin via a Dual-Mode Lewis Acid Induced Cascade Cyclization Approach” J. Org. Chem. 2013, 78, 7912.

    11.  Zhu, L.; Han, Y.; Du, G.; Lee, C.-S. “A Bifunctional Lewis Acid Induced Cascade Cyclization to the Tricyclic Core of ent-Kaurenoids and Its Application to the Formal Synthesis of (±)-Platensimycin” Org. Lett. 2013, 15, 524.

    12.  Liu, X.; Lee, C.-S. “Total Synthesis of (−)-Teucvidin” Org. Lett. 2012, 14, 2886.

    13.  He, S.; Li, H.; Yip, Y.-W.; Yeung, C.-T.; Fung, Y. O.; Kong, H.-K.; Yeung, H.-L.; Law, G.-L.; Wong, K.-L.; Lee, C.-S. Lam, M. H.-W.; Murphy, M. B.; Lam, P. K.-S.; Wong, W.-T. “Responsive Two-Photon Induced Europium Emission as Fluorescent Indicator for Paralytic Shellfish Saxitoxin” Org. Lett. 2011, 13, 5036.

    14.  Huang, S.; Du, G.; Lee, C.-S. “Construction of the Tricyclic Furanochroman Skeleton of Phomactin A via the Prins/Conia-Ene Cascade Cyclization Approach” J. Org. Chem. 2011, 76, 6534.

    Wu, W.; Min, L.; Zhu, L.; Lee, C.-S. “A New Class of Enantioselective Catalytic 2-Pyrone Diels-Alder Cycloadditions” Adv. Synth. Catal. 2011, 353, 1135.