Institute of Chemistry, Academia Sinica--Cheng-Chung Wang

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Carbohydrate Chemistry, Automated Synthesis of Glycocojugates and Glycobiology

Cheng-Chung Wang (王正中)

    886-2-55728618
    886-2-27831237
    wangcc7280 gate.sinica.edu.tw

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Research Fellow (2022-)；Associate Research Fellow (2017-2022)；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) ；

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.
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.
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.
Wu, C.-H.; Wang, C.-C. Strategies for Desymmetrising Trehalose to Synthesise Trehalose Glycolipids. Org. Biomol. Chem. 2014, 12, 5558.
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.
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.
Verma, V. P.; Wang, C.-C. Highly Stereoselective Glycosyl-Chloride-Mediated Synthesis of 2-Deoxyglucosides. Chem. Eur. J. 2013, 19, 846.
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.
Esposito, D.; Hurevich, M.; Castagner, B.; Wang, C.-C.; Seeberger, P. H. Automated synthesis of sialylated oligosaccharides. Beilstein J. Org. Chem. 2012, 8, 1601.
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.
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.
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.
Wang, C.-C.; Zulueta, M. M. L.; Hung, S.-C. Regioselective one-pot protection and protection-glycosylation of carbohydrates. Chimia 2011, 65, 54.
Shie, C.-R.; Tseng, J. H.; Wang, C.-C.; Hung, S.-C. J. Chin. Chem. Soc. 2009, 56, 510. (Best Article Award 2009)
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.
Wang, C.-C.; Kulkarni, S. S.; Hung, S.-C. Regioselective One-Pot Protection of Carbohydrates. Synform 2007, 3, A32. (Feature Article)
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.
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.
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.
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.
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.
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.
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.
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.
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

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.
Yeh Chun-Hong, Chang Ya-Jou, Lin Tsung-Juin, Wang Cheng-Chung* Total Synthesis of <i>Campylobacter jejuni</i> NCTC11168 Capsular Polysaccharide via the Intramolecular Anomeric Protection Strategy. Journal of the American Chemical Society 2023-04-11, 145, jacs.3c00102-jacs.3c00102.
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.
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.
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.
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.
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.
Chang Chun‐Wei, Lin Mei‐Huei, Wang Cheng‐Chung* Statistical Analysis of Glycosylation Reactions. Chemistry – A European Journal 2021, 27, 2556-2568.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Kesatebrhan Haile Asressu, Cheng-Chung Wang* Concise synthesis of 2,7-anhydrosialic acid derivatives and its application. Carbohydrate Research 2017, 453-454, 44-53.
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, .
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.
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.
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.
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.
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.
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.
Chia-Hui Wu, Cheng-Chung Wang* Strategies for desymmetrising trehalose to synthesise trehalose glycolipids. ORGANIC & BIOMOLECULAR CHEMISTRY 2014-04, 12, 5558-5562.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Shang-Cheng Hung*, Cheng-Chung Wang, Shankar R. Thopate Efficient Synthesis of L-Altrose and L-Mannose. TETRAHEDRON LETTERS 2000, 41, 3119-3122.