Shie Research Group
The Laboratory of Organic Synthesis and Chemical Biology
Institute of Chemistry, Academia Sinica, Taiwan
Effect of sulfotyrosine and negatively charged amino acid of leech-derived peptides on binding and inhibitory activity against thrombin
Chen, T.-Y.; Shyur, E.; Ma, T.-H.; Wijeyewickrema, L.; Lin, S.-W.; Kao, M.-R.; Liang, P.-H.; Shie, J.-J.; Chuang, E.-Y.; Liou, J.-P.; Hsieh, Y. S. Y.
ChemBioChem 2024, 25, e202300744.
Structural compositions and biological activities of cell wall polysaccharides in the rhizome, stem, and leaf of Polygonatum odoratum (Mill.) Druce
Li, J.; Hsiung, S.-Y.; Kao, M.-R.; Xing, X.; Chang, S.-C.; Wang, D.; Hsieh, P.-Y.; Liang, P.-H.; Zhu, Z.; Cheng, T.-J. R.; Shie, J.-J.; Liou, J.-P.; Abbott. D. W.; Kwon, S. W.; Hsieh, Y. S. Y.
Carbohydr. Res. 2022, 521, 108662.
Cannabinoid receptor 1 antagonist genistein attenuates marijuana-induced vascular inflammation
Wei, T.-T.; Chandy, M.; Nishiga, M.; Zhang, A.; Kumar, K. K.; Thomas, D.; Manhas, A.; Rhee, S.; Justesen, J. M.; Chen, I. Y.; Wo, H.-T.; Khanamiri, S.; Yang, J. Y.; Seidl, F. J.; Burns, N. Z.; Liu, C.; Sayed, N.; Shie, J.-J.; Yeh, C.-F.; Yang, K.-C.; Lau, E.; Lynch, K. L.; Rivas, M.; Kobilka, B. K.; Wu, J. C.
Cell 2022, 185, 1676–1693.
Polyglutamine-specific gold nanoparticle complex alleviates mutant Huntingtin-induced toxicity
Wahyuningtyas, D.; Chen, W.-H.; He, R.-Y.; Huang, Y.-A.; Tsao, C.-K.; He, Y.-J.; Yu, C.-Y.; Lu, P.-C.; Chen, Y.-C.; Wang, S.-H.; Ng, K. C.; Chen, B. P.-W.; Wei, P.-K.; Shie, J.-J.; Kuo, C.-H.; Sun, Y. H.; Huang, J. J.-T.
ACS Appl. Mater. Interfaces 2021, 13, 60894–60906.
Production of structurally defined chito-oligosaccharides with a single N-acetylation at their reducing end using a new discovered chitinase from Paenibacillus pabuli
Li, J.; Wang, D.; Chang, S.-C.; Liang, P.-H.; Srivastava, V.; Guu, S.-Y.; Shie, J.-J.; Khoo, K.-H.; Bulone, V.; Hsieh, Y. S. Y.
J. Agric. Food Chem. 2021, 69, 3371‒3379.
Identification of existing pharmaceuticals and herbal medicines as inhibitors of SARS-CoV-2 infection
Jan, J.-T.; Cheng, T.-J. R.; Juang, Y.-P.; Ma, H.-H.; Wu, Y.-T.; Yang, W.-B.; Cheng, C.-W.; Chen, X.; Chou, T.-H.; Shie, J.-J.; Cheng, W.-C.; Chein, R.-J.; Mao, S.-S.; Liang, P.-H.; Ma, C.; Hung, S.-C.; Wong, C.-H.
Proc. Natl. Acad. Sci. U. S. A. 2021, 118, e2021579118.
Before 2021
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Juang, Y.-P.; Lin, Y.-Y.; Chan, S.-H.; Shie, J.-J.; Hsieh, Y. S. Y.; Guh, J.-H.; Liang, P.-H. “Synthesis, distribution analysis and mechanism studies of N-acyl glucosamine-bearing oleanolic saponins.” Bioorg. Chem. 2020, 99, 103835. DOI: 10.1016/j.bioorg.2020.103835
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Lee, C.-H.; Chang, H.-W.; Yang, C.-T.; Wali, N.; Shie, J.-J.; Hsueh, Y.-P. “Sensory cilia as the Achilles heel of nematodes when attacked by carnivorous mushrooms.” Proc. Natl. Acad. Sci. U. S. A. 2020, 117, 6014‒6022. DOI: 10.1073/pnas.1918473117
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Shie, J.-J.; Fang, J.-M. “Development of effective anti-influenza drugs: congeners and conjugates – a review.” J. Biomed. Sci. 2019, 26, 84. DOI: 10.1186/s12929-019-0567-0
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Carillo, K. J. D.; Wu, D.; Lin, S.-C.; Tsai, S.-L.; Shie, J.-J.; Tzou, D.-L. M. “1H/13C Chemical shifts and cation binding dataset of the corticosteroid prednisolone titrated with metal cations.” Data in Brief 2019, 27, 104620. DOI: 10.1016/j.dib.2019.104620
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Carillo, K. D.; Wu, D.; Lin, S.-C.; Tsai, S.-L.; Shie, J.-J.; Tzou, D.-L. M. “Magnesium and calcium reveal different chelating effects in a steroid compound: A model study of prednisolone using NMR spectroscopy.” Steroids 2019, 150, 108429. DOI: 10.1016/j.steroids.2019.108429
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Wu, D.; Carillo, K. J. D.; Tsai, S.-L.; Shie, J.-J.; Tzou, D.-L. M. “Solid-state nuclear magnetic resonance investigation of neurosteroid compounds and magnesium interactions.” J. Chin. Chem. Soc. 2019, 66, 1318‒1326. DOI: 10.1002/jccs.201800458
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Lo, P.-W.; Shie, J.-J.; Chen, C.-H.; Wu, C.-Y.; Hsu, T.-L.; Wong, C.-H. “O-GlcNAcylation regulates the stability and enzymatic activity of the histone methyltransferase EZH2.” Proc. Natl. Acad. Sci. U. S. A. 2018, 115, 7302‒7307. DOI: 10.1073/pnas.1801850115
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Ho, Y.-H.; Ho S.-Y.; Hsu, C.-C.; Shie, J.-J.; Wang, T.-S. A. “Utilizing iron(III)-chelation masking strategy to prepare mono- and bis-functionalized aerobactin analogues for targeting pathogenic bacteria.” Chem. Commun. 2017, 53, 9265‒9268. DOI: 10.1039/c7cc05197b
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Kumar, V.; Shin, J. S.; Shie, J.-J.; Ku, K. B.; Kim, C.; Go, Y. Y.; Huang, K.-F.; Kim, M.; Liang, P.-H. “Identification and evaluation of potent Middle East respiratory syndrome coronavirus (MERS-CoV) 3CLPro inhibitors.” Antiviral Res. 2017, 141, 101‒106. DOI: 10.1016/j.antiviral.2017.02.007
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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, 1490‒1493. DOI: 10.1039/c6cc08805h
Before Institute of Chemistry, Academia Sinica
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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, 9953‒9961.
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Chen, C.-L.; Lin, T.-C.; Wang, S.-Y.; Shie, J.-J.; Tsai, K.-C.; Cheng, Y.-S. E.; Jan, J.-T.; Lin, C.-J.; Fang, J.-M.; Wong, C.-H. “Tamiphosphor monoesters as anti-influenza agents.” Eur. J. Med. Chem. 2014, 81, 106‒118.
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Chen, Y.-S.; Yu, H.-M.; Shie, J.-J.; Cheng, T.-J. R.; Wu, C.-Y.; Fang, J.-M.; Wong, C.-H. “Chemical constituents of Plectranthus amboinicus and the synthetic analogs possessing anti-inflammatory activity.” Bioorg. Med. Chem. 2014, 22, 1766‒1772.
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Cheng, T.-J. R.; Weinheimer, S.; Bart Tarbet, E.; Jan, J.-T.; Cheng, Y.-S. E.; Shie, J.-J.; Chen, C.-L.; Chen, C.-A.; Hsieh, W.-C.; Huang, P.-W.; Lin, W.-H.; Wang, S.-Y.; Fang, J.-M.; Hu, Y.-P. O.; Wong, C.-H. “Development of oseltamivir phosphonate congeners as anti-influenza agents.” J. Med. Chem. 2012, 55, 8657–8670.
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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, 17959–17965.
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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, 4451–4462.
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Cho, C.-C.; Liu, J.-N.; Chien, C.-H.; Shie, J.-J.; Chen, Y.-C.; Fang, J.-M. “Direct amidation of aldoses and decarboxylative amidation of α-keto acids: An efficient conjugation method for carbohydrate molecules.” J. Org. Chem. 2009, 74, 1549–1556.
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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, 7388–7398.
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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, 5788–5791.
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Su, C.-Y.; Wang, S.-Y.; Shie, J.-J.; Jeng, K.-S.; Temperton, N. J.; Fang, J.-M.; Wong, C.-H.; Cheng, Y.-S. E. “In vitro evaluation of neuraminidase inhibitors using the neuraminidase-dependent release assay of hemagglutinin-pseudotyped viruses.” Antiviral Res. 2008, 79, 199–205.
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Lee, J.-C.; Shih, S.-R.; Chang, T.-Y.; Tseng, H.-Y.; Shih, Y.-F.; Yen, K.-J.; Chen, W.-C.; Shie, J.-J.; Fang, J.-M.; Liang, P.-H.; Chao, Y.-S.; Hsu, J. T.-A. “A mammalian cell-based reverse two-hybrid system for functional analysis of 3C viral protease of human enterovirus 71.” Anal. Biochem. 2008, 375, 115–123.
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Lee, C.-C.; Kuo, C.-J.; Hsu, M.-F.; Liang, P.-H.; Fang, J.-M.; Shie, J.-J.; Wang, A. H.-J. “Structural basis of mercury- and zinc-conjugated complexes as SARS-CoV 3C-like protease inhibitors.” FEBS Lett. 2007, 581, 5454–5458.
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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, 11892–11893.
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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, 3141–3144.
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Wu, C.-Y.; King, K.-Y.; Kuo, C.-J.; Fang, J.-M.; Wu, Y.-T.; Ho, M.-Y.; Liao, C.-L.; Shie, J.-J.; Liang, P.-H.; Wong, C.-H. “Stable benzotriazole esters mechanism-based inactivators of the severe acute respiratory syndrome 3CL protease.” Chem. Biol. 2006, 13, 261–268.
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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, 5240–5252.
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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, 4469–4473.
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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, 2703–2707.
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Chen, M.-Y.; Hsu, J.-L.; Shie, J.-J.; Fang, J.-M. “Direct oxidative amidation of aldoses by iodine in ammonia water.” J. Chin. Chem. Soc. 2003, 50, 129–133.
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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, 1158–1160.
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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, 5208–5215.
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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, 1099–1102.
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Lee, A. S.-Y.; Yeh, H.-C.; Shie, J.-J. “A novel, highly efficient and selective desilylating method for trialkylsilyl ethers.” Tetrahedron Lett. 1998, 39, 5249–5252.
Review Articles
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Shie, J.-J.; Fang, J.-M. “Development of effective anti-influenza drugs: congeners and conjugates – a review.” J. Biomed. Sci. 2019, 26, 84. (Review) DOI: 10.1186/s12929-019-0567-0
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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, 757‒774. (Review)
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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, 127−141. (Mini review)
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Shie, J.-J.; Fang, J.-M. “The development of anti-influenza drugs: Rational structural-design neuraminidase inhibitors.” Chemistry 2008, 66, 279–292. (Special review written in Chinese)
Patents
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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. US 9874562 (2018).
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Wong, C.-H.; Fang, J.-M.; Shie, J.-J. “Reactive labelling compounds and their uses thereof.” US Patent No. US 9759726 (2017).
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Wong, C.-H.; Fang, J.-M.; Shie, J.-J. “Benzocyclooctyne compounds and their uses thereof.” US Patent No. US 9547009 (2017).
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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)