Tun-Cheng Chien
Name Tun-Cheng Chien
Email
Office Tel No. +886-2-77496126
Lab TEL +886-2-77496201
Title Professor
Research Organic, Bioorganic and Medicinal Chemistry
Research Specialization Research interests:
  1. Organic synthesis: The research focuses on the development of carbon-carbon, carbon-nitrogen, and nitrogen-nitrogen bond formation strategies for the construction of diverse nitrogen-containing compounds. The ultimate goal is to apply these methodologies for the synthesis of biologically interested molecules, natural products, and their analogs/derivatives.
  2. Bioorganic and medicinal chemistry: The research focuses on the design and synthesis of structurally and mechanistically diverse biological molecules and their analogs. The majority of this research effort is to study the interactions between small molecules and the targeting biological systems and to develop potentially active chemotherapeutic agents.
  1. Tang, H.; Wu, M.-H.; Lin, H.-Y.; Han, M.-R.; Tu, Y.-H.; Yang, Z.-J.; Chien, T.-C.;* Chan, N.-L.;* Chang, W.-c.* Mechanistic Analysis of Carbon–carbon Bond Formation by Deoxypodophyllotoxin Synthase. Proc. Natl. Acad. Sci. U. S. A. 2022, 119, e2113770119.
  2. Chen, T.-Y.; Xue, S.; Tsai, W.-C.; Chien, T.-C.;* Guo, Y.;* Chang, W.-c.* Deciphering Pyrrolidine and Olefin Formation Mechanism in Kainic Acid Biosynthesis. ACS Catal. 2021, 11, 278-282.
  3. Yu, C.-P.; Chang, H.-Y.; Chien, T.-C.* Total Synthesis of Pseudouridine via Heck-type C-Glycosylation. New J. Chem. 2019, 43, 8796-8803.
  4. Chang, W.-c.;* Yang, Z.-J.; Tu, Y.-H.; Chien, T.-C.* Reaction Mechanism of a Non-heme Iron Enzyme Catalyzed Oxidative Cyclization via C-C Bond Formation. Org. Lett. 2019, 21, 228-232.
  5. Liao, Z.-Y.; Yeh, W.-H.; Liao, P.-Y.; Liu, Y.-T.; Chen, Y.-C.; Chen, Y.-H.; Hsieh, T.-H.; Lin, C.-C.; Lu, M.-H.; Chen, Y.-S.; Hsu, M.-C.; Li, T.-K.;* Chien, T.-C.* Regioselective Synthesis and Biological Evaluation of N-Substituted 2-Aminoquinazolin-4-ones. Org. Biomol. Chem. 2018, 16, 4482-4494.
  6. Tsai, C.-H.; Tang, Y.-H.; Chen, H.-T.; Yao, Y.-W.; Chien, T.-C.;* Kao, C.-L.* A Selective Glucose Sensor: Cooperative Effect by Monoboronic Acid-modified Poly(amidoamine) Dendrimers. Chem. Commun. 2018, 54, 4577-4580.
  7. Hsieh, T.-H.; Liao, P.-Y.; Liu, Y.-T.; Wang, C.-H.; Lin, C.-C.; Chien, T.-C.* Investigation of O-Sulfonylation-promoted Heterolytic N-O Bond Cleavage of Amidoximes and Ketoximes. J. Chin. Chem. Soc. (Taipei) 2018, 65, 325-330. (special issue: International Symposium in Catalysis and Fine Chemicals 2016)
  8. Wang, Y.-R.; Chen, S.-F.; Wu, C.-C.; Liao, Y.-W.; Lin, T.-S.; Liu, K.-T.; Chen, Y.-S.; Li, T.-K.;* Chien, T.-C.;* Chan, N.-L.* Producing Irreversible Topoisomerase II-Mediated DNA Breaks by Site-Specific Pt(II)-Methionine Coordination Chemistry. Nucleic Acids Res. 2017, 45, 10861-10871.
  9. Liao, Z.-Y.; Liao, P.-Y.; Chien, T.-C.* CuI-catalyzed Intramolecular Aminocyanation of Terminal Alkynes in N-(2-Ethynylphenyl)-N-sulfonylcyanamides via Cu-vinylidene Intermediates. Chem. Commun. 2016, 52, 14404-14407.
  10. Shih, Y.-C.; Wang, J.-S.; Hsu, C.-C.; Tsai, P.-H.; Chien, T.-C.* Identification of Reactive Intermediates for the Decarbonylative Reaction of 1-Alkylprolines. Synlett, 2016, 27, 2841-2845.
  11. Wu, N.-L.; Lee, T.-A.; Wang, S.-F.; Li, H.-J.; Chen, H.-T.; Chien, T.-C.; Huang, C.-C.;* Hung, C.-F.* Green Fluorescent Protein Chromophore Derivative Suppresses Ultraviolet A-induced JNK-signalling and Apoptosis in Keratinocytes and Adverse Effects in Zebrafish Embryos. Exp. Dermatol. 2016, 25, 983-990.
  12. Wang, C.-H.; Hsieh, T.-H.; Lin, C.-C.; Yeh, W.-H.; Lin, C.-A.; Chien, T.-C.* One-Pot Synthesis of N-Monosubstituted Ureas from Nitriles via Tiemann Rearrangement. Synlett, 2015, 26, 1823-1826.
  13. Shih, Y.-C.; Tsai, P.-H.; Hsu, C.-C.; Chang, C.-W.; Jhong, Y.; Chen, Y.-C.; Chien, T.-C.* Biomimetic Approach toward the Total Synthesis of rac-2-(Acylmethylene)pyrrolidine Alkaloids. J. Org. Chem. 2015, 80, 6669–6678.
  14. Zeng, C.-J.; Chen, C.-J.; Chang, C.-W.; Chen, H.-T.;* Chien, T.-C.* Copper(I) Iodide-Catalyzed Synthesis of N,N’-Disubstituted Guanidines from N-Substituted Cyanamides. Aust. J. Chem. 2014, 67, 1134–1137. (invited manuscript in the special issue - Research Front on ‘The Chemistry of Guanidine, Guanidinium and Guanidinate Compounds’) 
  15. Lin, C.-C.; Hsieh, T.-H.; Liao, P.-Y.; Liao, Z.-Y.; Chang, C.-W.; Shih, Y.-C.; Yeh, W.-H.; Chien, T.-C.* Practical Synthesis of N-Substituted Cyanamides via Tiemann Rearrangement of Amidoximes. Org. Lett. 2014, 16, 892−895.
  16. Chang, C.-W.; Wu, C.-C.; Chang, Y.-Y.; Lin, C.-C.; Chien, T.-C.* Synthesis and Unexpected Oxidization of the Tricyclic Core of Ugibohlin, Isophakellin and Styloguanidine. J. Org. Chem. 2013, 78, 10459-10468.
  17. Shih, Y.-C.; Yang, Y.-Y.; Lin, C.-C.; Chien, T.-C.* Synthesis of 6-Alkyluridines from 6-Cyanouridine via Zinc(II) Chloride-Catalyzed Nucleophilic Substitution with Alkyl Grignard Reagents. J. Org. Chem. 2013, 78, 4027-4036.
  18. Cheng, C.; Shih, Y.-C.; Chen, H.-T.;* Chien, T.-C.* Regioselective Arylation of Uracil and 4-Pyridone Derivatives via Copper(I) Bromide Mediated C-H Bond Activation. Tetrahedron, 2013, 69, 1387-1396.
  19. Choi, S.-h.; Mansoorabadi, S. O.; Liu, Y.-n.; Chien, T.-C.; Liu, H.-w.* Analysis of UDP-D-Apiose/UDP-D-Xylose Synthase-Catalyzed Conversion of UDP-D-Apiose Phosphonate to UDP-D-Xylose Phosphonate: Implications for a Retroaldol-Aldol Mechanism. J. Am. Chem. Soc. 2012, 134, 13946-13949.
  20. Lee, C.-Y.; Chen, Y.-C.; Lin, H.-C.; Jhong, Y.; Chang, C.-W.; Tsai, C.-H.; Kao, C.-L.;* Chien, T.-C.* Facile Synthesis of 4-Arylidene-5-imidazolinones as Synthetic Analogs of Fluorescent Protein Chromophore. Tetrahedron, 2012, 68, 5898-5907.
  21. Lin, J.-B.; He, J.-L.; Shih, Y.-C.; Chien, T.-C.* Study on the Synthesis of 6-Alkylaminouridines via the Nucleophilic Aromatic Substitution Reaction of 6-Cyanouridine Derivatives. Tetrahedron Lett. 2011, 52, 3969-3972.
  22. Shih, Y.-C.; Chien, T.-C.* Practical Synthesis of 6-Aryluridines via Palladium(II) Acetate Catalyzed Suzuki-Miyaura Cross-coupling Reaction. Tetrahedron, 2011, 67, 3915-3923.
  23. Wu, Y.-J.; Liao, C.-C.; Jen, C.-H.; Shih, Y.-C.; Chien, T.-C.* Chemical Models and Their Mechanistic Implications for the Transformation of 6-Cyanouridine 5'-Monophosphate Catalyzed by Orotidine 5'-Monophosphate Decarboxylase. Chem. Commun. 2010, 46, 4821-4823.
  24. Jen, C.-H.; Chien, T.-C.* Reinvestigation of the Synthesis of 1-Deazauridine. Nucleosides Nucleotides Nucleic Acids, 2010, 29, 523-534.
  25. Chien, T.-C.; Chen, C.-S.; Chern, J.-W.* Nucleosides XIII. Facile Synthesis of 4-Amino-1-(2-deoxy-beta-D-ribofuranosyl)quinazolin-2-one as a 2'-Deoxycytidine Analog for Oligonucleotide Synthesis. J. Chin. Chem. Soc. (Taipei) 2005, 52, 1237-1244.
  26. Chien, T.-C.; Berry, D. A.; Drach, J. C.; Townsend, L. B.* Synthesis of 3-Aminoimidazo[4,5-c]pyrazole Nucleoside via the N-N Bond Formation Strategy as a [5:5] Fused Analog of Adenosine. Nucleosides Nucleotides Nucleic Acids, 2005, 24, 1971-1996.
  27. Chien, T.-C.; Kuo, C.-C.; Chen, C.-S.; Chern, J.-W.* Nucleoside XII. Synthesis of 5'-Modified Isoguanosines and Reinvestigation of 5'-Deoxy-N3,5'-cycloisoguanosine. J. Chin. Chem. Soc. (Taipei) 2004, 51, 1401-1406.
  28. Chien, T.-C.; Chen, C.-S.; Yu, F.-H.; Chern, J.-W.* Nucleosides XI. Synthesis and Antiviral Evaluation of 5'-Alkylthio-5'-deoxy Quinazolinone Nucleoside Derivatives as S-Adenosyl-L-homocysteine Analogs. Chem. Pharm. Bull. 2004, 52,1422-1426.
  29. Berry, D. A.; Chien, T.-C.; Townsend, L. B.* Mononuclear Heterocyclic Rearrangement: Synthesis of [5:5] Bicyclic [c]-Fused 3-Aminopyrazoles via the N-N Bond Formation Strategy. Heterocycles, 2004, 63, 2475-2494.
  30. Chien, T.-C.; Saluja, S. S.; Drach, J. C.; Townsend, L. B.* Synthesis and Antiviral Evaluation of Polyhalogenated Imidazole Nucleosides: Dimensional Analogs of 2,5,6-Trichloro-1-(beta-D-ribofuranosyl)benzimidazole. J. Med. Chem. 2004, 47, 5743-5752.
  31. Chien, T.-C.; Meade, E. A.; Hinkley, J. M.; Townsend, L. B.* Facile Synthesis of 1-Substituted 2-Amino-3-cyanopyrroles: New Synthetic Precursors for 5,6-Unsubstituted Pyrrolo[2,3-d]pyrimidines. Org. Lett. 2004, 6, 2857-2859.
  32. Chien, T.-C.; Smaldone, R. A.; Townsend, L. B.* Facile Synthesis of 1-Substituted 4,5-Diaminopyrazoles and Its Application Toward the Synthesis of Pyrazolo[3,4-b]pyrazines. Tetrahedron Lett. 2004, 45, 4105-4108.
  33. Chien, T.-C.; Chern, J.-W.* A Convenient Preparation of 1,2,3-Tri-O-acetyl-beta-D-ribofuranose by Enzymatic Regioselective 5-O-Deacetylation of the Peracetylated Ribofuranose (Nucleosides X.). Carbohydr. Res. 2004, 339, 1215-1217.
  34. Chen, G. S.; Chen, C.-S.; Chien, T.-C.; Yeh, J.-Y.; Kuo, C.-C.; Talekar, R. S.; Chern, J.-W.* Nucleosides IX. Synthesis of Purine N3,5'-Cyclonucleosides and N3,5'-Cyclo-2',3'-seconucleosides via Mitsunobu Reaction as TIBO-like Derivatives. Nucleosides Nucleotides Nucleic Acids, 2004, 23, 347-359.
  35. Chien, T.-C.; Chen, C.-S.; Yeh, J.-Y.; Wang, K.-C.; Chern, J.-W.* Nucleosides VII. Synthesis of N-Triphenylphosphoranylidene Nucleosides by Mitsunobu Reaction. A Novel Protecting Group for Primary Amines of Nucleosides. Tetrahedron Lett. 1995, 36, 7881-7884.
  1. Shih, Y.-C.; Liao, Y.-S.; Lin, C.-C.; Yang, Y.-Y.; Lin, J.-B.; Cheng, C.; He, J.-L.; Liao, Z.-Y.; Jen, C.-H.; Wu, Y.-J.; Chien, T.-C.* Synthesis of 6-Substituted Uracil and Uridine Derivatives. Collect. Symp. Ser. 2014, 14, 129-132.
  2. Chien, T.-C.;* Jen, C.-H.; Wu, Y.-J.; Liao, C.-C. Chemical Models and Their Mechanistic Implications for the Transformation of 6-Cyanouridine 5'-Monophosphate Catalyzed by Orotidine 5'-Monophosphate Decarboxylase. Nucleic Acids Symp. Ser. 2008, 52, 297-298.
  3. Chien, T.-C.;* Drach, J. C.; Townsend, L. B. Design and Synthesis of 1-(beta-D-Ribofuranosyl)imidazo[4,5-c]pyrazoles as 5:5 Bicyclic Analogs of Purine Nucleosides. Nucleic Acids Symp. Ser. 2008, 52, 593-594.
Country School Name Department Degree
Taiwan National Taiwan University Department of Chemistry B.S.
Taiwan National Defense Medical Center School of Pharmacy M.S.
U.S. University of Michigan Department of Chemistry Ph.D.
Organization Title Department Job Title Duration
Chung Yuan Christian University Department of Chemistry Adjunct Professor 2021.02 ~ Up to today
Kaohsiung Medical University Department of Medicinal and Applied Chemistry Professor (Joint Appointed) 2020.08 ~ Up to today
International Union of Pure and Applied Chemistry (IUPAC) Division VII: Chemistry and Human Health Division National Representative 2020.01 ~ Up to today
National Yang-Ming University Faculty of Pharmacy Adjunct Professor 2019.02 ~ Up to today
National Taiwan Normal University Department of Chemistry Professor 2017.08 ~ Up to today
National Taiwan Normal University Department of Chemistry Associate Professor 2012.02 ~ 2017.07
National Taiwan Normal University Department of Chemistry Assistant Professor 2006.08 ~ 2012.01
University of Texas at Austin College of Pharmacy Postdoctoral Fellow 2005.01 ~ 2006.01