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Cheng-Chung Wang (王正中)

Carbohydrate Chemistry, Automated Synthesis of Glycocojugates and Glycobiology

Cheng-Chung Wang (王正中)

researcherid:D-8946-2015     886-2-55728618
    886-2-27831237
    wangcc7280gate.sinica.edu.tw
    Cheng-Chung Wang '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.

Mechanism study of glycosylation reactions and development of stereoselective glycosylation reactions.

Mechanism study of glycosylation reactions

Synthesis of asymmetric trehalose derived glycolipids and their activity as adjuvants of anti-tuberculosis vaccine.

Synthesis of asymmetric trehalose derived glycolipids

Synthesis of asymmetric trehalose derived glycolipids

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. Kesatebrhan Haile Asressu, Cheng-Chung Wang* Concise synthesis of 2,7-anhydrosialic acid derivatives and its application. Carbohydrate Research 2017453-454, 44-53.
  2. 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, .
  3. 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.
  4. 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.
  5. 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.
  6. 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.
  7. 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.
  8. 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.
  9. Chia-Hui Wu, Cheng-Chung Wang* Strategies for desymmetrising trehalose to synthesise trehalose glycolipids. ORGANIC & BIOMOLECULAR CHEMISTRY 2014-0412, 5558-5562.
  10. 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.
  11. Ved Prakash Verma, Cheng-Chung Wang* Highly Stereoselective Glycosyl Chloride-Mediated Synthesis of 2-Deoxyglucosides. CHEMISTRY-A EUROPEAN JOURNAL 2013-0119(03), 846-851.
  12. 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.
  13. 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.
  14. 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.
  15. Cheng-Chung Wang*, Medel Manuel L. Zulueta, Shang-Cheng Hung* Regioselective one-pot protection and protection-glycosylation of carbohydrates.. CHIMIA 2011-0165, 54-58.
  16. 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.
  17. 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.
  18. 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.
  19. 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.
  20. 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.
  21. 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.
  22. 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.
  23. 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.
  24. 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.
  25. 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.
  26. 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.