張哲健 教授

通訊處

辦公室電話︰(02)2905-3564

實驗室電話：(02)2905-3562

E-mail

080686@mail.fju.edu.tw

學經歷

教授(2021.02~)      輔仁大學化學系

副教授(2015.08~2021.01) 輔仁大學化學系

助理教授(2010.02~2015.07) 輔仁大學化學系

博士後研究員(2010)        台灣大學藥學所

博士後研究員(2009)        美國Northwestern University

博士後研究員(2008)        加拿大University of Alberta

化學博士(2007)     國立台灣大學

訪問博士生(2006) 德國University of Münster DAAD

研究助理(2002)     中央研究院生化所

助教(2000)     台灣大學化學系

化學碩士(1999)     國立台灣大學

化學學士(1997)     國立中興大學

獎賞

德國學術交流署DAAD與國科會-三明治計畫獎學金 2005-2006

科技部特殊優秀人才獎勵(校內)-105、106學年度
國科會補助大專院校研究獎勵 (校內) - 111年度

學術專長

有機合成，生物有機，自由基聚合

研究領域

本實驗室研究主題是以有機合成 (organic synthesis) 的方法，來製備具有生物或是具藥物活性的有機分子。包含下面幾個主題:

(1)    天然物全合成 (natural product synthesis)，利用新的合成方法製備天然物，例如：SCH 71450 (一種治療過動的配方用藥);  ribulose-5-phosphate與xylulose-5-phosphate (人體戊醣磷酸代謝途徑的重要中間化合物)。

(2)    藥物合成 (new synthesis of drugs)，利用新開發的合成方法學來製備已知藥物，或是具有藥物活性的有機化合物，例如： Telbivudine (L-dT，SEBIVOTM，Novartis，喜必福，諾華，新一代治療B型肝炎的藥物);  Rolipram (PDE4 inhibitor，磷酸雙酯酶4型抑制劑，抗憂鬱與抗阿茲海默症療效);  Phenylpiracetam (Phenotropil，抗憂鬱與失智症藥物);  Phenylpiracetam hydrazide (fonturacetam hydrazide, 抗癲癇療效)

(3)    開發合成方法學 (synthetic methodologies)，例如:

(2-1) 利用羰基移位 (carbonyl translocation) 的合成方法學，將便宜的醣原料 (carbohydrate raw material)，轉換為重要昂貴且稀有的合成建構組元，醣類分子，或是具生物活性分子，如: 2-去氧-L-核醣 (2-deoxy-L-ribose)，3-去氧-L-果糖 (3-deoxy-L-fructose)，核酮醣 (D-ribulose)，木酮醣 (D-xylulose)，2-去氧-L-核醣核苷 (L-deoxyribonucleoside)

(2-2) 利用乙烯自由基 (vinyl radical) 進行ipso合環反應 (ipso cyclization) 來合成天然物或是藥物的結構骨架，如: b-苯基-g-內醯胺 (b-aryl-g-lactam)，不飽和-b-苯基-g-內醯胺 (unsaturated-b-aryl-g-lactam)。

(4)    控制的活性自由基聚合反應 (controlled living radical polymerization)，例如: 設計合成醣類聚合物單體上含有與癌細胞表面上有關的醣類分子 (tumor-associated carbohydrate antigens)，並利用控制的活性自由基聚合，來製備具有癌症相關抗原醣分子，如Tn的醣類聚合物，希望能模擬合成醣類抗癌疫苗 (anticancer vaccines)。

(5)    設計與合成有機藥物分子 (design and synthesis of drug-like molecules)，例如:設計合成找出具高度選擇性鴉片類受體 (opioid receptor) 的拮抗劑 (antagonists)，以發展新型的止痛劑 (pain killers)。

代表著作

代表著作：

Independent research (獨立研究工作，唯一通訊作者)
21.   New Synthesis of β-Aryl-GABA Drugs

        Pei-Ling Wang (王沛淩), Yi-Xuan Chan (詹翊瑄), Che-Chien Chang*

Tetrahedron 2023, 146, 133648.

20.   From a Carbohydrate Raw Material to an Important Building Block: Cost-efficient Conversion of D-Fructose into 2-Deoxy-L-ribose

Ya-Han Hsu (許雅涵), Che-Chien Chang*

J. Org. Chem. 2022, 87, 13308-13314.

19   Cascade Vinyl Radical Ipso-Cyclization Reactions and the Formation of a,b-Unsaturated-b-aryl-g-lactams from N-Propargyl Benzamides

       Chih-Hao Luo (駱致豪), Pei-Ling Wang (王沛淩), Che-Chien Chang*

       J. Org. Chem. 2021, 86, 15033-15044.

18.  Conversion of a Readily Available Carbohydrate Raw Material into a Rare L-Deoxyhexose

       Ya-Han Hsu (許雅涵), Che-Chien Chang*

       Tetrahedron Lett. 2021, 63, 152718.

17. Design and Synthesis of Trivalent Tn Glycoconjugate Polymers by Nitroxide-Mediated Polymerization

Si-Xian Liu(劉思嫺), Yun-Tzu Tsai (蔡芸慈), Yu-Tung Lin (林禹彤), Jia-Yue Li(李佳樾), and Che-Chien Chang*

Tetrahedron 2019, 75, 130776.

16.  Synthesis of L-Deoxyribonucleosides from D-Ribose.

Wei-Syun Song (宋韋勳), Si-Xian Liu(劉思嫺), and Che-Chien Chang*

       J. Org. Chem. 2018, 83, 14923-14932. 

15.  Chemical Synthesis of Ketopentose-5-phosphates.

Wei-Chih Wei (魏瑋志) and Che-Chien Chang*

Eur. J. Org. Chem. 2017, 3033-3040. 

獲選為當期的期刊封面故事: http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201700685/full

14.  Synthesis of 3-Deoxy-L-ketohexoses Through Group Transfer.

Tai-Ni Lu (盧岱妮) and Che-Chien Chang*

J. Org. Chem. 2016, 81, 469-475. 

13.  Radical Cyclization Followed by the Fragmentation of Carbonyl Compounds: Effect of an alpha-Benzoyl Group.

Li-An Chien(簡勵安) and Che-Chien Chang*

J. Org. Chem. 2015, 80, 11294-11301.

12.  Chemical synthesis of 1-deoxy-L-fructose and L-sorbose through carbonyl translocation.

Hsin-Pei Wu(吳欣蓓), Nai-Yun Hsu(許乃云), Tai-Ni Lu (盧岱妮), and Che-Chien Chang*

Eur. J. Org. Chem. 2015, 378-382.

11.  Synthetic mimics of carbohydrate-based anticancer vaccines: preparation of carbohydrate polymers bearing unimolecular trivalent carbohydrate ligands

by controlled living radical polymerization.

Teng-Yuan Kuo(郭騰元), Li-An Chien(簡勵安), Ya-Chi Chang(張亞綺), Shuang-Yu Liou(劉相妤), and Che-Chien Chang*

RSC Adv., 2014, 4, 47066-47075.

10.  The absolute stereochemical assignment of SCH 71450, a selective dopamine D4 receptor antagonist, through the enantioselective epimer synthesis.

Hsin-Pei Wu(吳欣蓓), Tai-Ni Lu (盧岱妮), Nai-Yun Hsu(許乃云), and Che-Chien Chang*

Eur. J. Org. Chem. 2013, 2898-2905.

9.  A unique synthetic method to convert a D-sugar into 2-deoxy-L-ribitol through carbonyl translocation.

Nai-Yun Hsu(許乃云) and Che-Chien Chang*

Eur. J. Org. Chem. 2013, 658-661.

 

 

Selected Invited Lectures (重要會議邀請演講)

 

Dec 12, 2019, Session 78-3, The 18th Asian Chemical Congress (18ACC), Taipei, Taiwan

“Formal Total Synthesis of Telbivudine (L-dT)”

Nov 22, 2018, SIL-12A, The 13th International Symposium on Organic Reactions (ISOR-13), Hsinchu, Taiwan.

“Synthesis of L-Deoxyribonucleosides from D-Ribose”

Apr 22, 2016, SIL-2B, The 12th International Symposium on Organic Reactions (ISOR-12), Kyoto, Japan.

“Carbonyl Translocation in the Synthesis of Deoxysugars”

May 01, 2015, 科技部有機合成小組研討會, 中興大學惠蓀林場

“Radicals in the Synthesis of Deoxysugars and Glycopolymers”

Dec 04, 2010, 中國化學會年會, 台灣大學浦大邦講堂

“Antagonism of Dihydropyridines Toward Voltage Dependent Ca2+ Channels, Cav1.3 and Cav1.2”

 

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Before FJCU

 

Postdoc work (Canada and United States)

8.     Farzad Malihi, Derrick. L. J. Clive,* Che-Chien Chang and Minaruzzaman, Synthetic studies on CP-225,917 and CP-263,114: Access to advanced tetracyclic systems by intramolecular conjugate displacement and [2,3]-Wittig rearrangement, J. Org. Chem. 2013, 78, 996-1013.  (with Clive)

7.     Che-Chien Chang, Song Cao, Soosung Kang, Li Kai, Xinyong Tian, Prativa Pandey, Sara Fernandez Dunne, Chi-Hao Luan, D. James Surmeier*, Richard B. Silverman*, Antagonism of 4-substituted 1,4-dihydropyridine-3,5-dicarboxylates toward voltage-dependent L-type Ca2+ channels Cav1.3 and Cav1.2, Bioorg. Med. Chem. 2010, 18, 3147-3158. (with Silverman)

 

PhD work (Taiwan and Germany)

6.   Che-Chien Chang, Yu-Hsien Kuo and Yeun-Min Tsai*, The synthesis of carbohydrate-derived acylsilanes and their intramolecular free radical cyclization with the formation of polyoxygenated cyclopentanes, Tetrahedron Lett. 2009, 50, 3805-3808.   (with Tsai)

5.   Che-Chien Chang, Kai O. Siegenthaler and Armido Studer*, A new sterically highly hindered 7-membered cyclic nitroxide for the controlled living radical polymerization, Helv. Chim. Acta, 2006, 89, 2200-2210. (with Studer)

4.     Che-Chien Chang and Armido Studer*, Acceleration of the styryl-TEMPO mediated controlled radical styrene-polymerization by addition of an efficient alkoxyamine, Macromolecules, 2006, 39, 4062-4068.     (with Studer)

 

Before PhD

3.     Wen-Bin Yang, Yu-ing Yang, Yu-Feng Gu, Shwu-Huey Wang, Che-Chien Chang, and Chun-Hung Lin*, Stereochemistry in the synthesis and reaction of exo-glycals, J. Org. Chem. 2002, 67, 3773-3782.

2.     Chuan-Fa Chang, Wen-Bin Yang, Che-Chien Chang and Chun-Hung Lin*, Inter- and intramolecular alcohol additions to exo-glycals, Tetrahedron Lett. 2002, 43, 6515-6519.

1.     Wen-Bin Yang, Chung-Yi Wu, Che-Chien Chang, Shwu-Huey Wang, Chin-Fen Teo and Chun-Hung Lin*, Facile synthesis of conjugated exo-glycals, Tetrahedron lett. 2001, 42, 6907-6910.