Wang, Cheng-Chung

Carbohydrate Chemistry, Automated Synthesis of Glycocojugates and Glycobiology

Wang, Cheng-Chung (王正中)

    886-2-27898618
    886-2-27831237
    wangcc7280
    Wang, Cheng-Chung 's Lab
Associate Research Fellow (2017-);Assistant Research Fellow (2009-2017 );Postdoctoral Fellow, Max-Planck-Institute of Colloids and Interfaces, Germany (2009);Postdoctoral Fellow, Swiss Federal Institute of Technology (ETH), Switzerland (2008-2009);Postdoctoral Fellow, National Tsing Hua University (2007-2008);Ph. D., Chemical Biology and Molecular Biophysics Program, Academia Sinica in Cooperation with Department of Chemistry, National Tsing Hua University (2002-2007);Research Assistant, Institute of Chemistry, Academia Sinica (1999-2002);B.S. & M. S., Department of Chemistry, National Sun Yat-Sen University (1993-1999);
Research Interests

Our researches are focused on the synthesis of glycoconjugates, such as oligosaccharides, glycolipids and glycopeptides. Our current projects currently include:

  1. Mechanism study of glycosylation reactions and development of stereoselective glycosylation reactions.
  2. Synthesis of asymmetric trehalose derived glycolipids and their activity as adjuvants of anti-tuberculosis vaccine.
  3. Automated synthesis of glycoconjugates.

探討醣鏈結反應的反應機制,並以之為基礎,控制醣鏈結反應的立體選擇性。

探討醣鏈結反應的反應機制,並以之為基礎,控制醣鏈結反應的立體選擇性。

以海藻糖為中心的不對稱醣脂質之合成研究,並測試其做為抗結核菌疫苗佐劑之活性。

以海藻糖為中心的不對稱醣脂質之合成研究,並測試其做為抗結核菌疫苗佐劑之活性。



Selected Publications
  1. Joseph, A. A.; Dhurandhare, V. M.; Chang, C.-W.; Verma, V. P.; Mishra, G. P.; Ku, C.-C.; Lin, C.-C.; Wang, C.-C. Chemoselective Per-O-trimethylsilylation and Homogeneous N-Functionalisation of Amino Sugars. Chem. Commun. 2015, 51, 104.
  2. Ko, Y.-C.; Tsai, C.-F.; Wang, C.-C.; Dhurandhare, V. M.; Hu, P.-L.; Su, T.-Y.; Lico, L. S.; Zulueta, M. M. L.; Hung, S.-C. Microwave-Assisted One-Pot Synthesis of 1,6-Anhydrosugars and Orthogonally-Protected Thioglycosides. J. Am. Chem. Soc. 2014, 136, 14425.
  3. Li, Y.-C.; Ho, I.-H.; Ku, C.-C.; Zhong, Y.-Q.; Hu, Y.-P.; Chen, Z.-G.; Chen, C.-Y.; Lin, W.-C.; Zulueta, M. M. L.; Hung, S.-C.; Lin, M.-G.; Wang, C.-C.; Hsiao, C.-D. Interactions That Influence the Binding of Synthetic Heparan Sulfate Based Disaccharides to Fibroblast Growth Factor-2. ACS Chem. Biol. 2014, 9, 1712.
  4. Wu, C.-H.; Wang, C.-C. Strategies for Desymmetrising Trehalose to Synthesise Trehalose Glycolipids. Org. Biomol. Chem. 2014, 12, 5558.
  5. Farr, T. D.; Lai, C.-H.; Grünstein, D.; Orts-Gil, G.; Wang, C.-C.; Boehm-Sturm, P.; Seeberger, P. H.; Harms, C. Imaging Early Endothelial Inflammation Following Stroke by Core Shell Silica Superparamagnetic Glyconanoparticles That Target Selectin. Nano Lett. 2014, 14, 2130.
  6. Joseph, A. A.; Chang, C.-W.; Wang, C.-C. Simple One-pot Regioselective 6-O- Phosphorylation of Carbohydrates and Trehalose Desymmetrization. Chem. Commun. 2013, 49, 11497.
  7. Verma, V. P.; Wang, C.-C. Highly Stereoselective Glycosyl-Chloride-Mediated Synthesis of 2-Deoxyglucosides. Chem. Eur. J. 2013, 19, 846.
  8. Hu, Y.-P.; Zhong, Y.-Q.; Chen, Z.-G. Chen; Chen, C.-Y.; Shi, Z.; Zulueta, M. M. L.; Ku, C.-C.; Lee, P.-Y.; Wang, C.-C.; Hung, S.-C. Divergent Synthesis of 48 Heparan Sulfate-Based Disaccharides and Probing the Specific Sugar−Fibroblast Growth Factor-1 Interaction. J. Am. Chem. Soc. 2012, 134, 20722.
  9. Esposito, D.; Hurevich, M.; Castagner, B.; Wang, C.-C.; Seeberger, P. H. Automated synthesis of sialylated oligosaccharides. Beilstein J. Org. Chem. 2012, 8, 1601.
  10. Lröck, L.; Esposito, D.; Castagner, B.; Wang, C.-C.; Bindschadler, P. M.; Seeberger, P. H. Streamlined Access to Conjugation-Ready Glycans by Automated Synthesis. Chem. Sci. 2012, 3, 1617.
  11. Joseph, A. A.; Verma, V. P.; Liu, X.-Y,; Wu, C.-H.; Dhurandhare, V.; Wang, C.-C.  TMSOTf-Catalyzed Silylation: Streamlined Regioselective One-Pot Protection and Aceylation of Carbohydrates. Eur. J. Org. Chem. 2012, 744.
  12. Wang, C.-C.; Kulkarni, S. S.; Zulueta, M. M. L.; Hung, S.-C. Synthesis of Hemagglutinin-Binding Trisaccharides, in The Molecular Immunology of Complex Carbohydrates-3, Advances in Experimental Medicine and Biology 705, Springer Science+Business Media, LLC, 2011, Chapter 37, pp 691-726.
  13. Wang, C.-C.; Zulueta, M. M. L.; Hung, S.-C. Regioselective one-pot protection and protection-glycosylation of carbohydrates. Chimia 2011, 65, 54.
  14. Shie, C.-R.; Tseng, J. H.; Wang, C.-C.; Hung, S.-C. J. Chin. Chem. Soc. 2009, 56, 510. (Best Article Award 2009)
  15. Wang, C.-C.; Kulkarni, S. S.; Lee, J.-C.; Luo, S.-Y.; Hung, S.-C. Regioselective One-pot Protection of Glucose. Nat. Protoc. 2008, 3, 97.
  16. Wang, C.-C.; Kulkarni, S. S.; Hung, S.-C. Regioselective One-Pot Protection of Carbohydrates. Synform 2007, 3, A32. (Feature Article)
  17. Wang, C.-C.; Lee, J.-C.; Luo, S.-Y.; Kulkarni, S. S.; Huang, Y.-W.; Lee, C.-C.; Chang, K.-L.; Hung, S.-C. Regioselective One-pot Protection of Carbohydrates. Nature 2007, 446, 896.
  18. Lee, J.-C.; Chang, S.-W.; Chi, F.-C.; Chen, C.-S.; Wen, Y.-S.; Wang, C.-C.; Kulkarni, S. S.; Puranik, R.; Liu, Y.-H.; Hung, S.-C. From D-Glucose to Biologically Potent L-Hexose Derivatives: Synthesis of a-L-Iduronidase Fluorogenic Detector and the Disaccharide Moieties of Bleomycin A2 and Heparan Sulfate. Chem. Eur. J. 2004, 10, 399.
  19. Lu, X.-A.; Chou, C.-H.; Wang, C.-C.; Hung, S.-C. Regioselective Esterification of Various D-Glucopyranosides: Synthesis of a Fully Protected Disaccharide Unit of Hyaluronic Acid. Synlett. 2003, 1364.
  20. Wang, C.-C.; Lee, J.-C.; Luo, S.-Y.; Fan, H.-F.; Pai, C.-L.; Yang, W.-C.; Hung, S.-C. Synthesis of Biologically Potent a1→2-Linked Disaccharide Derivatives via Regioselective One-Pot Protection-Glycosylation. Angew. Chem., Int. Ed. Engl. 2002, 41, 2360.
  21. Wang, C.-C.; Luo, S.-Y.; Shie, C.-R.; Hung, S.-C. Metal Trifluoromethanesulfonate- Catalyzed Regioselective Borane-Reductive Ring Opening of Benzylidene Acetals:  A Concise Synthesis of 1,4-Dideoxy-1,4-imino-L-xylitol. Org. Lett. 2002, 4, 847.
  22. Hung, S.-C.; Thopate, S. R.; Wang, C.-C. Regioselective and Stereoselective Benzoylation of 2-N-Protected 4,6-O-Ketal Derivatives of D-Glucosamines with 1-(Benzoyloxy)benzotriazole. Carbohydr. Res. 2001, 330, 177.
  23. Hung, S.-C.; Thopate, S. R.; Chi, F.-C.; Chang, S.-W.; Lee, J.-C.; Wang, C.-C.; Wen, Y.-S.1,6-Anhydro-β-L-hexopyranoses as Potent Synthons in the Synthesis of the Disaccharide Units of Bleomycin A2 and Heparin. J. Am. Chem. Soc. 2001, 123, 3153.
  24. Hung, S.-C.; Wang, C.-C.; Chang, S.-W.; Chen, C.-S.1,6-Anhydro-β-L-hexopyranoses as Valuable Building Blocks Toward the Synthesis of L-Gulosamine and L-Altrose Derivatives. Tetrahedron Lett. 2001, 42, 1321.
  25. Hung, S.-C.; Wang, C.-C.; Thopate, S. R.Efficient Synthesis of L-Altrose and L-Mannose. Tetrahedron Lett. 2000, 41, 3119.

Update: 2015-03-23

Journal Paper
  1. Vijay M. Dhurandhare, Yuh-Sheng Wen, Sachin D. Gawande, Pin-Hsuan Liao, Cheng-Chung Wang* Synthesis of Galactosamine and Allosamine Derivatives via a Microwave-assisted Preparation of 1,6-anhydroglucosamine. JOURNAL OF ORGANIC CHEMISTRY 2016-10, .
  2. Mei-Yuan Hsu, Yi-Pei Liu, Sarah Lam, Su-Ching Lin, Cheng-Chung Wang* TMSBr-mediated Solvent- and Workup-Free Synthesis of α-2-Deoxyglycosides from Glycals. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 2016-0412, 1758–1764.
  3. Kathleen D. Carillo, Susan Arco, Cheng-Chung Wang, Der-Lii M. Tzou* Solid-state NMR investigation of effect of fluorination and methylation on prednisolone conformation. STEROIDS 2015-12104, 263-269.
  4. Vijay M. Dhurandhare, Girija Prasad Mishra, Sarah Lam, Cheng-Chung Wang* Direct Synthesis of Methyl Phosphoramidates in Carbohydrates. ORGANIC & BIOMOLECULAR CHEMISTRY 2015-0713(36), 9457-9461.
  5. A. Abragam Joseph, Vijay M. Dhurandhare, Chun-Wei Chang, Ved Prakash Verma, Girija Prasad Mishra, Chiao-Chu Ku, Chun-Cheng Lin,* Cheng-Chung Wang*  Chemoselective per-O-trimethylsilylation and homogeneous N-functionalisation of amino sugars . CHEMICAL COMMUNICATIONS 2015-0151, 104.
  6. Yen-Chun Ko, Cheng-Fang Tsai, Cheng-Chung Wang*, Vijay M. Dhurandhare, Pu-Ling Hu, Ting-Yang Su, Larry S. Lico, Medel Manuel L. Zulueta, Shang-Cheng Hung Microwave-Assisted One-Pot Synthesis of 1,6-Anhydrosugars and Orthogonally Protected Thioglycosides. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 2014-10136, 14425-14431.
  7. Yi-Ching Li, I-Hsin Ho, Chiao-Chu Ku, Yong-Qing Zhong, Yu-Peng Hu, Zhi-Geng Chen, Chun-Yen Chen, Wei-Chen Lin, Medel Manuel L. Zulueta, Shang-Cheng Hung*, Min-Guan Lin, Cheng-Chung Wang, Chwan-Deng Hsiao* Interactions That Influence the Binding of Synthetic Heparan Sulfate Based Disaccharides to Fibroblast Growth Factor‑2. ACS CHEMICAL BIOLOGY 2014-06 9, 1712-1717.
  8. Chia-Hui Wu, Cheng-Chung Wang* Strategies for desymmetrising trehalose to synthesise trehalose glycolipids. ORGANIC & BIOMOLECULAR CHEMISTRY 2014-0412, 5558-5562.
  9. A. Abragam Joseph, Chun-Wei Chang, Cheng-Chung Wang* Simple One-pot Regioselective 6-O-Phosphorylation of Carbohydrates and Trehalose Desymmetrization. CHEMICAL COMMUNICATIONS 2013-1149, 11497-11499.
  10. Ved Prakash Verma, Cheng-Chung Wang* Highly Stereoselective Glycosyl Chloride-Mediated Synthesis of 2-Deoxyglucosides. CHEMISTRY-A EUROPEAN JOURNAL 2013-0119(03), 846-851.
  11. Davide Esposito, Mattan Hurevich, Bastien Castagner, Cheng-Chung Wang, Peter H. Seeberger* Automated synthesis of sialylated oligosaccharides. Beilstein Journal of Organic Chemistry 2012-098, 1601.
  12. Lenz Krock, Davide Esposito, Bastien Castagner, Cheng-Chung Wang, Pascal Bindschadler, Peter H. Seeberger* Streamlined access to conjugation-ready glycans by automated synthesis. Chemical Science 2012-033(5), 1617~1622.
  13. A. Abragam Joseph, Ved Prakash Verma, Xin-Yi Liu, Chia-Hui Wu, Vijay Dhurandhare, Cheng-Chung Wang* TMSOTf-Catalyzed Silylation: Streamlined Regioselective One-Pot Protection and Aceylation of Carbohydrates.. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2012-022012, 744-753.
  14. Cheng-Chung Wang*, Medel Manuel L. Zulueta, Shang-Cheng Hung* Regioselective one-pot protection and protection-glycosylation of carbohydrates.. CHIMIA 2011-0165, 54-58.
  15. Chi-Rung Shie, Zheng-Hao Tzeng, Cheng-Chung Wang, Shang-Cheng Hung* Metal Trifluoromethanesulfonate-Catalyzed Regioselective Reductive Ring Opening of Benzylidene Acetals.. JOURNAL OF THE CHINESE CHEMICAL SOCIETY 200956, 510-523.
  16. Cheng-Chung Wang, Suvarn S. Kulkarni, Jinq-Chyi Lee, Shun-Yuan Luo, Shang-Cheng Hung* Regioselective One-pot Protection of Glucose.. Nature Protocols 20083, 97-113.
  17. Cheng-Chung Wang, Jinq-Chyi Lee, Shun-Yuan Luo, Suvarn S, Kulkarni, Yu-Wen Huang, Chia-Chen Lee, Ken-Lien Chang, Shang-Cheng Hung* Regioselective One-pot Protection of Carbohydrates.. NATURE 2007446, 896-899.
  18. Jinq-Chyi Lee, Shu-Wen Chang, Fa-Chen Chi, Chien-Sheng Chen, Yuh-Sheng Wen, Cheng-Chung Wang, Suvarn S. Kulkarni, Ramachandra Puranik, Yi-Hung Liu, Shang-Cheng Hung* From D-Glucose to Biologically Potent L-Hexose Derivatives: Synthesis of -L-Iduronidase Fluorogenic Detector and the Disaccharide Moieties of Bleomycin A2 and Heparan Sulfate. . CHEMISTRY-A EUROPEAN JOURNAL 200410, 399-415.
  19. Xin-An Lu, Chien-Hung Chou, Cheng-Chung Wang, Shang-Cheng Hung* Regioselective Esterification of Various D-Glucopyranosides: Synthesis of a Fully Protected Disaccharide Unit of Hyaluronic Acid.. SYNLETT 2003, 1364-1366.
  20. Cheng-Chung Wang, Shun-Yuan Luo, Shang-Cheng Hung* Metal Trifluoromethanesulfonate- Catalyzed Regioselective Borane-Reductive Ring Opening of Benzylidene Acetals: A Concise Synthesis of 1,4-Dideoxy-1,4-imino-L-xylitol.. ORGANIC LETTERS 20024, 847-849.
  21. Cheng-Chung Wang, Jinq-Chyi Lee, Shun-Yuan Luo, Hsin-Fang Fan, Chin-Ling Pai, Wei-Chieh Yang, Lung-Dai Lu, Shang-Cheng Hung* Synthesis of Biologically Potent 1→2-Linked Disaccharide Derivatives via Regioselective One-Pot Protection-Glycosylation.. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 200241, 2360-2362.
  22. Shang-Cheng Hung*, Cheng-Chung Wang, Shu-Wen Chang, Chien-Sheng Chen  1,6-Anhydro-β-l-hexopyranoses as Valuable Building Blocks Toward the Synthesis of L-Gulosamine and L-Altrose Derivatives.. TETRAHEDRON LETTERS 200142, 1321-1324.
  23. Shang-Cheng Hung*, Shankar R. Thopate, Fa-Chen Chi, Shu-Wen Chang, Jinq-Chyi Lee, Cheng-Chung Wang, Yu-Sheng Wen 1,6-Anhydro-β-l-hexopyranoses as Potent Synthons in the Synthesis of the Disaccharide Units of Bleomycin A2 and Heparin.. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 2001123, 3153-3154.
  24. Shang-Cheng Hung*, Shankar R. Thopate, Cheng-Chung Wang  Regioselective and Stereoselective Benzoylation of 2-N-Protected 4,6-O-Ketal Derivatives of D-Glucosamines with 1-(Benzoyloxy)benzotriazole.. CARBOHYDRATE RESEARCH 2001330, 177-182.
  25. Shang-Cheng Hung*, Cheng-Chung Wang, Shankar R. Thopate Efficient Synthesis of L-Altrose and L-Mannose. TETRAHEDRON LETTERS 200041, 3119-3122.
Chapter of Publication
  1. Wang, C.-C., Kulkarni, S. S., Zulueta, M. M. L., Hung, S.-C.*, 2011, “Synthesis of Hemagglutinin-Binding Trisaccharides, in The Molecular Immunology of Complex Carbohydrates-3”, editor(s): Albert M. Wu, Advances in Experimental Medicine and Biology #705: The Molecular Immunology of Complex Carbohydrates-3, pp. 697-726, New York: Springer.