Shie, Jiun-Jie

Organic Synthesis, Chemical Biology and Drug Discovery

Shie, Jiun-Jie (謝俊結)

Assistant Research Fellow (2015-);Postdoctoral Fellow, The Genomics Research Center, Academia Sinica (2010-2015);Postdoctoral Fellow, The Scripps Research Institute, USA (2009-2010);Postdoctoral Fellow, The Genomics Research Center, Academia Sinica (2005-2009);Ph.D., Department of Chemistry, National Taiwan University (2002-2005);M.S., Department of Chemistry, National Taiwan University (1999-2002);B.S., Department of Chemistry, Tamkang University (1995-1999) ;
Research Interests

Our research interests are primarily in the areas of synthetic chemistry and chemical biology. We are interested in using organic chemistry as chemical tools to study and address in biology. The foremost focus centers on the developing new biorthogonal chemical reactions and related fluorescence smart probes for selective labeling of biomolecules in cells to understand cellular processes. In the field of synthetic chemistry, our research aims to develop new synthetic methodologies for the efficient and economical synthesis of complex glycoconjugates of biomedical significance and carbohydrate-based small molecular inhibitors against infection diseases.

~ Antiviral and antibacterial drug discovery.
~ Fluorescence-forming probes upon chemical reaction.
~ Development of novel bioorthogonal reactions in biological systems.
~ Fluorescent labeling chemistry of biomolecule in cell.

Selected Publications
  1. Shie, J.-J.; Liu, Y.-C.; Hsiao, J.-C.; Fang, J.-M.; Wong, C.-H. A cell-permeable and triazole-forming fluorescence probe for glycoconjugate imaging in live cells. Chem. Commun. 2017, 53, 1490.
  2. Shie, J.-J.; Liu, Y.-C.; Lee, Y.-M.; Lim, C.; Fang, J.-M.; Wong, C.-H. An azido-BODIPY probe for glycosylation: initiation of strong fluorescence upon triazole formation. J. Am. Chem. Soc. 2014, 136, 9953.
  3. Cheng, C.-K.; Tsai, C.-H.; Shie, J.-J.; Fang, J.-M. From neuraminidase inhibitors to conjugates: a step towards better anti-influenza drugs? Future Med. Chem. 2014, 6, 757. (Review)
  4. Shie, J.-J.; Fang, J.-M. Phosphonate congeners of oseltamivir and zanamivir as effective anti-influenza drugs: design, synthesis and biological activity. J. Chin. Chem. Soc. 2014, 61, 127. (Review)
  5. Shie, J.-J.; Fang, J.-M.; Lai, P.-T.; Wen, W.-H.; Wang, S.-Y.; Cheng, Y.-S. E.; Tsai, K.-C.; Yang, A.-S.; Wong, C.-H. A practical synthesis of zanamivir phosphonate congeners with potent anti-influenza activity. J. Am. Chem. Soc. 2011, 133, 17959.
  6. Shie, J.-J.; Chen, C.-A.; Lin, C.-C.; Ku, A. F.; Cheng, T.-J. R.; Fang, J.-M.; Wong, C.-H. Regioselective synthesis of di-C-glycosylflavones possessing anti-inflammation activities. Org. Biomol. Chem. 2010, 8, 4451.
  7. Shie, J.-J.; Fang, J.-M. The development of anti-influenza drugs: Rational structural-design neuraminidase inhibitors. Chemistry 2008, 66, 279. (Review in Chinese)
  8. Kuo, C.-J.; Shie, J.-J.; Fang, J.-M.; Yen, G.-R.; Hsu, J. T.-A.; Liu, H.-G.; Tseng, S.-N.; Chang, S.-C.; Lee, C.-Y.; Shih, S.-R.; Liang, P.-H. Design, synthesis, and evaluation of 3C protease inhibitors as anti-enterovirus 71 agents. Bioorg. Med. Chem. 2008, 16, 7388.
  9. Shie, J.-J.; Fang, J.-M.; Wong, C.-H. A concise and flexible synthesis of the potent anti-influenza agents tamiflu and tamiphosphor. Angew. Chem. 2008, 120, 5872‒5875; Angew. Chem. Int. Ed. 2008, 47, 5788.
  10. Shie, J.-J.; Fang, J.-M.; Wang, S.-Y.; Tsai, K.-C.; Cheng, Y.-S. E.; Yang, A.-S.; Hsiao, S.-C.; Su, C.-Y.; Wong, C.-H. Synthesis of tamiflu and its phosphonate congeners possessing potent anti-influenza activity. J. Am. Chem. Soc. 2007, 129, 11892.
  11. Shie, J.-J.; Fang, J.-M. Microwave-assisted one-pot tandem reactions for direct conversion of primary alcohols and aldehydes to triazines and tetrazoles in aqueous media. J. Org. Chem. 2007, 72, 3141.
  12. Shie, J.-J.; Fang, J.-M.; Kuo, T.-H.; Kuo, C.-J.; Liang, P.-H.; Huang, H.-J.; Wu, Y.-T.; Jan, J.-T.; Cheng, Y.-S. E.; Wong, C.-H. Inhibition of the severe acute respiratory syndrome 3CL protease by peptide- mimetic α,β-unsaturated esters. Bioorg. Med. Chem. 2005, 13, 5240.
  13. Shie, J.-J.; Fang, J.-M.; Kuo, C.-J.; Kuo, T.-H.; Liang, P.-H.; Huang, H.-J.; Yang, W.-B.; Lin, C.-H.; Chen, J.-L.; Wu, Y.-T.; Wong, C.-H. Discovery of potent anilide inhibitors against the severe acute respiratory syndrome 3CL protease. J. Med. Chem. 2005, 48, 4469.
  14. Shie, J.-J.; Workman, P. S.; Evans, W. J.; Fang, J.-M. Comparative study of TmI2, SmI2, and SmI2/HMPA in the cross-coupling reactions of 2-acetylthiophene and thiophene-2-carboxylate with carbonyl compounds. Tetrahedron Lett. 2004, 45, 2703.
  15. Shie, J.-J.; Fang, J.-M. Direct conversion of aldehydes to amides, tetrazoles, and triazines in aqueous media by one-pot tandem reactions. J. Org. Chem. 2003, 68, 1158.
  16. Yang, S.-M.; Shie, J.-J.; Fang, J.-M.; Nandy, S. K.; Chang, H.-Y.; Lu, S.-H.; Wang, G. Synthesis of polysubstituted benzothiophenes and sulfur containing polycyclic aromatic compounds via samarium diiodide promoted three-component coupling reactions of thiophene-2-carboxylate. J. Org. Chem. 2002, 67, 5208.
  17. Shie, J.-J.; Yang, S.-M.; Chen, C.-T.; Fang, J.-M. A novel photochromic system of 4,5-dialkenylthiophenes constructed by the samarium diiodide promoted coupling reactions of thiophene-2-carboxylate with aryl ketones. Org. Lett. 2002, 4, 1099.
    Selected Patents:
  1. Wong, C.-H.; Fang, J.-M.; Shie, J.-J. “Reactive labelling compounds and their uses thereof.” US Patent Application Publication (2015). Pub. No.: US 2015/0309041 A1.
  2. Wong, C.-H.; Fang, J.-M.; Shie, J.-J. “Benzocyclooctyne compounds and their uses thereof.” US Patent Application Publication (2015). Pub. No.: US 2015/0241439 A1.
  3. Wong, C.-H.; Fang, J.-M.; Cheng, Y.-S.; Shie, J.-J. “Zanamivir phosphonate congeners with anti-influenza activity and determining oseltamivir susceptibility of influenza viruses.” US Patent No. 9403855 (2016).
  4. Wong, C.-H.; Fang, J.-M.; Shie, J.-J.; Cheng, Y.-S. E.; Jan, J.-T. “Synthesis of oseltamivir containing phosphonate congeners with anti-influenza activity.” US Patent No. US 7888337 (2011).

Update: 2017-03-06

Journal Paper
  1. Vathan Kumar, Jin Soo Shin, Jiun-Jie Shie, Keun Bon Ku, Chonsaeng Kim, Yun Young Go, Kai-Fa Huang, Meehyein Kim*, Po-Huang Liang* Identification and evaluation of potent Middle East respiratory syndrome coronavirus (MERS-CoV) 3CLPro inhibitors. Antiviral Research 2017-03141, 101-106.
  2. Jiun-Jie Shie*, Ying-Chih Liu, Jye-Chian Hsiao, Jim-Min Fang, Chi-Huey Wong* A Cell-Permeable and Triazole-Forming Fluorescent Probe for Glycoconjugate Imaging in Live Cells . CHEMICAL COMMUNICATIONS 2017-0153, 1490-1493.
  3. Jiun-Jie Shie, Ying-Chih Liu, Yu-Ming Lee, Carmay Lim, Jim-Min Fang, Chi-Huey Wong* An Azido-BODIPY Probe for Glycosylation: Initiation of Strong Fluorescence upon Triazole Formation. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 2014-07136, 9953-9961.
  4. Chun-Lin Chen, Tzu-Chen Lin, Shi-Yun Wang, Jiun-Jie Shie, Keng-Chang Tsai, Yih-Shyun E. Cheng, Jia-Tsrong Jan, Chun-Jung Lin*, Jim-Min Fang*, Chi-Huey Wong* Tamiphosphor Monoesters as Effective Anti-influenza Agents. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY 2014-0681, 106-118.
  5. Chung-Kai Cheng, Chen-Hsuan Tsai, Jiun-Jie Shie, Jim-Min Fang* From Neuraminidase Inhibitors to Conjugates: A Step towards Better Anti-Influenza Drugs. Future Medicinal Chemistry 2014-056, 757-774.
  6. Yuan-Siao Chen, Hui-Ming Yu, Jiun-Jie Shie, Ting-Jen Rachel Cheng, Chung-Yi Wu*, Jim-Min Fang*, Chi-Huey Wong* Chemical Constituents of Plectranthus Amboinicus and the Synthetic Analogs Possessing Anti-Inflammatory Activity. BIOORGANIC & MEDICINAL CHEMISTRY 2014-0322, 1766-1772.
  7. Jiun-Jie Shie, Jim-Min Fang* Phosphonate Congeners of Oseltamivir and Zanamivir as Effective Anti-influenza Drugs: Design, Synthesis and Biological Activity. JOURNAL OF THE CHINESE CHEMICAL SOCIETY 2014-0161, 127-141.
  8. Ting-Jen R. Cheng, Steven Weinheimer, E. Bart Tarbet, Jia-Tsrong Jan, Yih-Shyun E. Cheng, Jiun-Jie Shie, Chun-Lin Chen, Chih-An Chen, Wei-Che Hsieh, Pei-Wei Huang, Wei-Hao Lin, Shi-Yun Wang, Jim-Min Fang*, Oliver Yoa-Pu Hu*, Chi-Huey Wong* Development of Oseltamivir Phosphonate Congeners as Anti-Influenza Agents. JOURNAL OF MEDICINAL CHEMISTRY 2012-1055, 8657-8670.
  9. Jiun-Jie Shie, Jim-Min Fang*, Po-Ting Lai, Wen-Hsien Wen, Shi-Yun Wang, Yih-Shyun E. Cheng, Keng-Chang Tsai, An-Suei Yang, Chi-Huey Wong* A Practical Synthesis of Zanamivir Phosphonate Congeners with Potent Anti-Influenza Activity. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 2011-11133, 17959-17965.
  10. Jiun-Jie Shie, Chih-An Chen, Chih-Chien Lin, Angela Fay Ku, Cheng, T.-J. R.; Ting-Jen R. Cheng, Jim-Min Fang*, Chi-Huey Wong* Regioselective Synthesis of Di-C-Glycosylflavones Possessing Anti-Inflammation Activities. ORGANIC & BIOMOLECULAR CHEMISTRY 2010-108, 4451-4462.
  11. Chia-Ching Cho, Jia-Nan Liu, Chung-Hsun Chien, Jiun-Jie Shie, Ting-Chu Chen, Jim-Min Fang* Direct Amidation of Aldoses and Decarboxylative Amidation of α-Keto Acids: An Efficient Conjugation Method for Carbohydrate Molecules. JOURNAL OF ORGANIC CHEMISTRY 2009-0274, 1549-1556.
  12. Ching-Yao Su, Shi-Yun Wang, Jiun-Jie Shie, King-Song Jeng, Nigel J. Temperton, Jim-Min Fang, Chi-Huey Wong, Yih-Shyun E. Cheng* In Vitro Evaluation of Neuraminidase Inhibitors Using the Neuraminidase-Dependent Release Assay of Hemagglutinin-Pseudotyped Viruses. ANTIVIRAL RESEARCH 2008-0979, 199-205.
  13. Chih-Jung Kuo, Jiun-Jie Shie, Jim-Min Fang*, Guei-Rung Yen, John T.-A. Hsu, Hun-Ge Liu, Sung-Nain Tseng, Shih-Cheng Chang, Ching-Yin Lee, Shin-Ru Shih, Po-Huang Liang* Design, Synthesis, and Evaluation of 3C Protease Inhibitors as Anti-Enterovirus 71 Agents. BIOORGANIC & MEDICINAL CHEMISTRY 2008-0816, 7388-7398.
  14. Jiun-Jie Shie, Jim-Min Fang*, Chi-Huey Wong A Concise and Flexible Synthesis of the Potent Anti-Influenza Agents Tamiflu and Tamiphosphor. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 2008-0647, 5788-5791.
  15. Jin-Ching Lee, Shin-Ru Shih, Ten-Yuan Chang, Huan-Yi Tseng, Ya-Feng Shih, Kuei-Jung Yen, Wei-Chun Chen, Jiun-Jie Shie, Jim-Min Fang, Po-Huang Liang, Yu-Sheng Chao, John T.-A. Hsu* A Mammalian Cell-Based Reverse Two-Hybrid System for Functional Analysis of 3C Viral Protease of Human Enterovirus 71. ANALYTICAL BIOCHEMISTRY 2008-04375, 115-123.
  16. 謝俊結, 方俊民* 流感藥物的設計與發展. 化學 2008第六十六卷第四期, 頁279-292.
  17. Cheng-Chung Lee, Chih-Jung Kuo, Min-Feng Hsu, Po-Huang Liang, Jim-Min Fang, Jiun-Jie Shie, Andrew H.-J. Wang* Structural Basis of Mercury- and Zinc-Conjugated Complexes as SARS-CoV 3C-Like Protease Inhibitors. FEBS LETTERS 2007-11581, 5454-5458.
  18. Jiun-Jie Shie, Jim-Min Fang*, Shi-Yun Wang, Keng-Chang Tsai, Yih-Shyun E. Cheng, An-Suei Yang, Shih-Chia Hsiao, Ching-Yao Su, Chi-Huey Wong Synthesis of Tamiflu and Its Phosphonate Congeners Possessing Potent Anti-Influenza Activity. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 2007-10129, 11892-11893.
  19. Jiun-Jie Shie, Jim-Min Fang* Microwave-Assisted One-Pot Tandem Reactions for Direct Conversion of Primary Alcohols and Aldehydes to Triazines and Tetrazoles in Aqueous Media. JOURNAL OF ORGANIC CHEMISTRY 2007-0472, 3141-3144.
  20. Chung-Yi Wu, Ke-Yung King, Chih-Jung Kuo, Jim-Min Fang, Ying-Ta Wu, Ming-Yi Ho, Chung-Lin Liao, Jiun-Jie Shie, Po-Huang Liang, Chi-Huey Wong* Stable Benzotriazole Esters Mechanism-Based Inactivators of the Severe Acute Respiratory Syndrome 3CL Protease. CHEMISTRY & BIOLOGY 2006-0313, 261-268.
  21. Jiun-Jie Shie, Jim-Min Fang*, Tun-Hsun Kuo, Chih-Jung Kuo, Po-Huang Liang*, Hung-Jyun Huang, Ying-Ta Wu, Jia-Tsrong Jan, Yih-Shyun E. Cheng, Chi-Huey Wong Inhibition of the Severe Acute Respiratory Syndrome 3CL Protease by Peptidomimetic α,β-Unsaturated Esters. BIOORGANIC & MEDICINAL CHEMISTRY 2005-0913, 5240-5252.
  22. Jiun-Jie Shie, Jim-Min Fang*, Chih-Jung Kuo, Tun-Hsun Kuo, Po-Huang Liang*, Hung-Jyun Huang, Wen-Bin Yang, Chun-Hung Lin, Jiun-Ling Chen, Yin-Ta Wu, Chi-Huey Wong Discovery of Potent Anilide Inhibitors Against the Severe Acute Respiratory Syndrome 3CL Protease. JOURNAL OF MEDICINAL CHEMISTRY 2005-0648, 4469-4473.
  23. Jiun-Jie Shie, Penny S Workman, William J Evans, Jim-Min Fang* Comparative Study of TmI2, SmI2, and SmI2/HMPA in the Cross-Coupling Reactions of 2-Acetylthiophene and Thiophene-2-carboxylate with Carbonyl Compounds. TETRAHEDRON LETTERS 2004-0345, 2703-2707.
  24. Jiun-Jie Shie, Jim-Min Fang* Direct Conversion of Aldehydes to Amides, Tetrazoles, and Triazines in Aqueous Media by One-Pot Tandem Reactions . JOURNAL OF ORGANIC CHEMISTRY 2003-0268,1158-1160.
  25. Ming‐Yi Chen, Jue‐Liang Hsu, Jiun‐Jie Shie, Jim‐Min Fang* Direct Oxidative Amidation of Aldoses by Iodine in Ammonia Water. JOURNAL OF THE CHINESE CHEMICAL SOCIETY 2003-0250, 129-133.
  26. Shyh-Ming Yang, Jiun-Jie Shie, Jim-Min Fang*, Sandip Kumar Nandy, Hung-Yu Chang, Syn-Hung Lu, Gladys Wang Synthesis of Polysubstituted Benzothiophenes and Sulfur-Containing Polycyclic Aromatic Compounds via Samarium Diiodide Promoted Three-Component Coupling Reactions of Thiophene-2-carboxylate. JOURNAL OF ORGANIC CHEMISTRY 2002-0767, 5208-5215.
  27. Jiun-Jie Shie, Shyh-Ming Yang, Chao-Tsen Chen, Jim-Min Fang* A Novel Photochromic System of 4,5-Dialkenylthiophenes Constructed by the Samarium Diiodide Promoted Coupling Reactions of Thiophene-2-carboxylate with Aryl Ketones. ORGANIC LETTERS 2002-044, 1099-1102.