主框架
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王正中 (Cheng-Chung Wang)

有機醣化學、自動化醣共軛分子合成及醣生物學

王正中 (Cheng-Chung Wang)

    886-2-55728618
    886-2-27831237
    wangcc7280gate.sinica.edu.tw

圖片連結(另開視窗)

研究員(111年迄今);副研究員(106年至111年);助研究員(98-106年);德國波茲坦馬克斯普朗克研究所博士後研究(98年);瑞士聯邦理工學院 (ETH) 博士後研究(97年至98年);國立清華大學博士後研究(96年至97年);中央研究院國際研究生學程-化學生物及分子生物物理學程及國立清華大學化學系博士(91年至96年);中央研究院化學所研究助理(88年至91年);國立中山大學化學系理學士、碩士(82年至88年) ;
研究領域

本實驗是目前主要研方向主要為醣共軛分子,如多醣以及醣脂質及醣胜肽的合成。其中包括:

  1. 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。
  2. 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。
  3. 醣共軛分子的自動化合成。

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

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

以海藻糖為中心的不對稱醣脂質之合成研究

代表作
  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

期刊論文
  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 2023-10-189(42), eadk0531.
  2. 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 2023-04-11145, 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 2021-07-220, 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 2021-07-2111(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 2021-07-1623, 0000-0000.
  6. 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 2021-02-2660(22), 12413-12423.
  7. Weldu Welday Desta, Wang Cheng-Chung* Selective Acetylation of Non-anomeric Groups of per-O-Trimethylsilylated Sugars. The Journal of Organic Chemistry 2021-02-2686, 10.1021/acs.joc.0c02813.
  8. Chang Chun‐Wei, Lin Mei‐Huei, Wang Cheng‐Chung* Statistical Analysis of Glycosylation Reactions. Chemistry – A European Journal 202127, 2556-2568.
  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 20216(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 202119(25), 5521-5524.
  11. 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 202186(24), 17906-17917.
  12. 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.
  13. 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.
  14. 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.
  15. 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.
  16. 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.
  17. 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 202026(1), 181-185.
  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 2019-09-1358(47), 16775-16779.
  19. Kesatebrhan Haile Asressu, Cheng-Chung Wang* Concise synthesis of 2,7-anhydrosialic acid derivatives and its application. Carbohydrate Research 2017453-454, 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 2016-0412, 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 2015-12104, 263-269.
  23. Vijay M. Dhurandhare, Girija Prasad Mishra, Sarah Lam, Cheng-Chung Wang* Direct Synthesis of Methyl Phosphoramidates in Carbohydrates. ORGANIC & BIOMOLECULAR CHEMISTRY 2015-0713(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 2015-0151, 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 2014-10136, 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 2014-0412, 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 2013-1149, 11497-11499.
  29. Ved Prakash Verma, Cheng-Chung Wang* Highly Stereoselective Glycosyl Chloride-Mediated Synthesis of 2-Deoxyglucosides. CHEMISTRY-A EUROPEAN JOURNAL 2013-0119(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 2012-098, 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 2012-033(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 2012-022012, 744-753.
  33. Cheng-Chung Wang*, Medel Manuel L. Zulueta, Shang-Cheng Hung* Regioselective one-pot protection and protection-glycosylation of carbohydrates.. CHIMIA 2011-0165, 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 200956, 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 20083, 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 2007446, 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 200410, 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, 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.
  40. 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.
  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 2001330, 177-182.
  42. 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.
  43. 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.
  44. Shang-Cheng Hung*, Cheng-Chung Wang, Shankar R. Thopate Efficient Synthesis of L-Altrose and L-Mannose. TETRAHEDRON LETTERS 200041, 3119-3122.
專書(論文集)之一章
  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.