Institute of Chemistry, Academia Sinica

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.

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

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

1. Chun-Wei Chang, Mei-Huei Lin, Tsun-Yi Chiang, Tzu0Chun Lin, Chia-Hui Wu, Cheng-Chung Wang* Unraveling the promoter effect and the roles of counterion exchange in glycosylation reaction. SCIENCE ADVANCES 2023-10-18, 9(42), eadk0531.
2. Yeh Chun-Hong, Chang Ya-Jou, Lin Tsung-Juin, Wang Cheng-Chung* Total Synthesis of Campylobacter jejuni NCTC11168 Capsular Polysaccharide via the Intramolecular Anomeric Protection Strategy. Journal of the American Chemical Society 2023-04-11, 145, jacs.3c00102-jacs.3c00102.
3. Kesatebrhan Haile Asressu, Chun-Wei Chang, Sarah Lam, Cheng-Chung Wang* Donor Reactivity-controlled Sialylation Reactions. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2021-07-22, 0, 00-00.
4. Chieh-Kai Chan *, Chien-Yu Lai, Cheng-Chung Wang* Environmentally Friendly Nafion-Catalyzed Synthesis of Substituted 2-Ethyl-3-Methylquinolines from Aniline and Propionaldehyde under Microwave Irradiation. CATALYSTS 2021-07-21, 11(8), 877-897.
5. Lin Mei-Huei, Chang Chun-Wei, Chiang Tsun-Yi, Dhurandhare Vijay M., Wang Cheng-Chung* Thiocarbonyl as a Switchable Relay-Auxiliary Group in Carbohydrate Synthesis. Organic Letters 2021-07-16, 23, 0000-0000.
6. Weldu Welday Desta, Wang Cheng-Chung* Selective Acetylation of Non-anomeric Groups of per-O-Trimethylsilylated Sugars. The Journal of Organic Chemistry 2021-02-26, 86, 10.1021/acs.joc.0c02813.
7. Chang Chun-Wei, Lin Mei-Huei, Chan Chieh-Kai, Su Kuan-Yu, Wu Chia-Hui, Lo Wei-Chih, Lam Sarah, Cheng Yu-Ting, Liao Pin-Hsuan, Wong Chi-Huey*, Wang Cheng-Chung* Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions. Angewandte Chemie International Edition 2021-02-26, 60(22), 12413-12423.
8. Weldu Welday Desta, Wang Cheng-Chung Rationalizing the Stereoelectronic Influence of Interglycosidic Bond Conformations on the Reactivity of 1,4-O-Linked Disaccharide Donors. The Journal of Organic Chemistry 2021, 86(24), 17906-17917.
9. Asressu Kesatebrhan Haile, Chan Chieh-Kai, Wang Cheng-Chung* One-Pot Synthesis of 1,5-Diketones under a Transition-Metal-Free Condition: Application in the Synthesis of 2,4,6-Triaryl Pyridine Derivatives. ACS Omega 2021, 6(11), 7296-7311.
10. Liu Ya-Zhou, Mu Xiao, Chan Chieh-Kai, Robeyns Koen, Wang Cheng-Chung, Singleton Michael L.* Water binding stabilizes stacked conformations of ferrocene containing sheet-like aromatic oligoamides. Organic & Biomolecular Chemistry 2021, 19(25), 5521-5524.
11. Chang Chun‐Wei, Lin Mei‐Huei, Wang Cheng‐Chung* Statistical Analysis of Glycosylation Reactions. Chemistry – A European Journal 2021, 27, 2556-2568.
12. Chan Chieh-Kai, Lai Chien-Yu, Wang Cheng-Chung* TMSOTf-catalyzed synthesis of substituted quinazolines using hexamethyldisilazane as a nitrogen source under neat and microwave irradiation conditions. Organic & Biomolecular Chemistry 2020, 18(36) 7201-7212.
13. Liu Ya‐Zhou, Wang Hu, Chan Chieh‐Kai, Mu Xiao, Robeyns Koen, Wang Cheng‐Chung, Singleton Michael L.* Structure‐Dependent Guest Recognition with Flexible Ferrocene‐Based Aromatic Oligoamide β‐Sheet Mimics. Chemistry – A European Journal 2020, 26(1), 181-185.
14. Chang Chun-Wei, Lin Mei-Huei, Wu Chia-Hui, Chiang Tsun-Yi, Wang Cheng-Chung* Mapping Mechanisms in Glycosylation Reactions with Donor Reactivity: Avoiding Generation of Side Products. The Journal of Organic Chemistry 2020, 85(24) 15945-15963.
15. Chan Chieh-Kai, Lai Chien-Yu, Wang Cheng-Chung* Environmentally Friendly Nafion-Mediated Friedländer Quinoline Synthesis under Microwave Irradiation: Application to One-Pot Synthesis of Substituted Quinolinyl Chalcones. Synthesis 2020, 52(12) 1779-1794.
16. Hsu Mei-Yuan, Lam Sarah, Wu Chia-Hui, Lin Mei-Huei, Lin Su-Ching, Wang Cheng-Chung* Direct Dehydrative Glycosylation Catalyzed by Diphenylammonium Triflate. Molecules 2020, 25(5) 1103.
17. Lam Sarah, Hsu Mei‐Yuan, Wang Cheng‐Chung Regio‐ and stereoselective glycosylation of 2‐( o ‐dihydroxyborylbenzyl) thioglucoside and unprotected methyl glycosides. Journal of the Chinese Chemical Society 2020, 67(3) 446-450.
18. Chun‐Wei Chang, Chia‐Hui Wu, Mei‐Huei Lin, Pin‐Hsuan Liao, Chun‐Chi Chang, Hsiao‐Han Chuang, Su‐Ching Lin Dr. Sarah Lam, Ved Prakash Verma, Chao‐Ping Hsu*, Cheng‐Chung Wang* Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity.. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 2019-09-13, 58(47), 16775-16779.
19. Kesatebrhan Haile Asressu, Cheng-Chung Wang* Concise synthesis of 2,7-anhydrosialic acid derivatives and its application. Carbohydrate Research 2017, 453-454, 44-53.
20. 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, .
21. 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 2016-04, 12, 1758–1764.
22. 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 2015-12, 104, 263-269.
23. Vijay M. Dhurandhare, Girija Prasad Mishra, Sarah Lam, Cheng-Chung Wang* Direct Synthesis of Methyl Phosphoramidates in Carbohydrates. ORGANIC & BIOMOLECULAR CHEMISTRY 2015-07, 13(36), 9457-9461.
24. 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 2015-01, 51, 104.
25. 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 2014-10, 136, 14425-14431.
26. 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.
27. Chia-Hui Wu, Cheng-Chung Wang* Strategies for desymmetrising trehalose to synthesise trehalose glycolipids. ORGANIC & BIOMOLECULAR CHEMISTRY 2014-04, 12, 5558-5562.
28. A. Abragam Joseph, Chun-Wei Chang, Cheng-Chung Wang* Simple One-pot Regioselective 6-O-Phosphorylation of Carbohydrates and Trehalose Desymmetrization. CHEMICAL COMMUNICATIONS 2013-11, 49, 11497-11499.
29. Ved Prakash Verma, Cheng-Chung Wang* Highly Stereoselective Glycosyl Chloride-Mediated Synthesis of 2-Deoxyglucosides. CHEMISTRY-A EUROPEAN JOURNAL 2013-01, 19(03), 846-851.
30. Davide Esposito, Mattan Hurevich, Bastien Castagner, Cheng-Chung Wang, Peter H. Seeberger* Automated synthesis of sialylated oligosaccharides. Beilstein Journal of Organic Chemistry 2012-09, 8, 1601.
31. 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 2012-03, 3(5), 1617~1622.
32. 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 2012-02, 2012, 744-753.
33. Cheng-Chung Wang*, Medel Manuel L. Zulueta, Shang-Cheng Hung* Regioselective one-pot protection and protection-glycosylation of carbohydrates.. CHIMIA 2011-01, 65, 54-58.
34. 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 2009, 56, 510-523.
35. Cheng-Chung Wang, Suvarn S. Kulkarni, Jinq-Chyi Lee, Shun-Yuan Luo, Shang-Cheng Hung* Regioselective One-pot Protection of Glucose.. Nature Protocols 2008, 3, 97-113.
36. 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 2007, 446, 896-899.
37. 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 2004, 10, 399-415.
38. 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.
39. 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 2002, 4, 847-849.
40. 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 2002, 41, 2360-2362.
41. 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 2001, 330, 177-182.
42. 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 2001, 42, 1321-1324.
43. 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 2001, 123, 3153-3154.
44. Shang-Cheng Hung*, Cheng-Chung Wang, Shankar R. Thopate Efficient Synthesis of L-Altrose and L-Mannose. TETRAHEDRON LETTERS 2000, 41, 3119-3122.

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.