張哲健
學歷
學校 | 系所 | 學位 |
---|---|---|
國立臺灣大學 | 化學系 | 博士 |
國立台灣大學 | 化學系 | 碩士 |
國立中興大學 | 化學系 | 學士 |
經歷
期間 | 單位 | 部門 | 職稱 |
---|---|---|---|
2021.02~ | 輔仁大學 | 化學系 | 教授 |
2015.08~2021.01 | 輔仁大學 | 化學系 | 副教授 |
2010.02~2015.07 | 輔仁大學 | 化學系 | 助理教授 |
2010 | 台灣大學 | 藥學所 | 博士後研究員 |
2009 | 美國Northwestern University | 化學系 | 博士後研究員 |
2008 | 加拿大University of Alberta | 化學系 | 博士後研究員 |
2006 | 德國University of Münster DAAD | 有機化學所 | 訪問博士生 |
2002 | 中央研究院 | 生化所 | 研究助理 |
2000 | 台灣大學 | 化學系 | 助教 |
CCC Lab
介紹
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。
「有機合成」實驗室
- 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)。
- 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)
- 新型態的合成方法學 (new synthetic methodologies),例如:(3-1) 以羰基移位 (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-去氧-4′-硫-D-木醣苷 (2-deoxy-4′-thio-D-xyloside)。(3-2) 利用級聯型的自由基反應 (cascade radical) 進行 乙烯基合環反應 (vinyl radical ipso) 與苯基移位 (1,4-aryl migration) 反應,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)。
- 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)。
- 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)。
學術著作
Independent research (獨立研究工作,唯一通訊作者)
代表著作:
22. First total synthesis of 2-deoxy-4′-thio-D-xyloside, a precursor for synthesis of D-2-deoxy-4′-thionucleosides
Ya-Han Hsu(許雅涵), Yi-Ting Yang(楊奕廷), Ya-Jie Tsai (蔡雅絜), Che-Chien Chang*
Tetrahedron 2024, 162, 134090.
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*
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*
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*
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*
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*
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.
09. 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.
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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.
畢業生發表論文
畢業生數 | 畢業生 | 英文姓名 | 縮寫 | 學生作者排序 | 發表論文期刊 |
1 | 許乃云 | Nai-Yun Hsu | NYH | 第一作者,且唯一作者 | Eur. J. Org. Chem. 2013, 658-661. |
2 | 郭騰元 | Teng-Yuan Kuo | TYK | 第一作者 | RSC Adv. 2014, 4, 47066-47075. |
3 | 吳欣蓓 | Hsin-Pei Wu | HPW | 第一作者
第一作者 |
1) Eur. J. Org. Chem. 2013, 2898-2905.
2) Eur. J. Org. Chem. 2015, 378-382. |
4 | 簡勵安 | Li-An Chien | LAC | 第一作者,且唯一作者 | J. Org. Chem. 2015, 80, 11294-11301. |
5 | 盧岱妮 | Tai-Ni Lu | TNL | 第一作者,且唯一作者 | J. Org. Chem. 2016, 81, 469-475. |
6 | 魏瑋志 | Wei-Chih Wei | WCW | 第一作者,且唯一作者
期刊封面 |
Eur. J. Org. Chem. 2017, 3033-3040.
with front cover |
7 | 蔡芸慈 | Yun-Tzu Tsai | YTT | 第二作者 | Tetrahedron 2019, 75, 130776. |
8 | 宋瑋勳 | Wei-Syun Song | WSS | 第一作者 | J. Org. Chem. 2018, 83, 14923-14932. |
9 | 劉思嫺 | Si-Xian Liu | SXL | 第一作者 | Tetrahedron 2019, 75, 130776. |
10 | 駱致豪 | Chih-Hao Luo | CHL | 第一作者 | J. Org. Chem. 2021, 86, 15033-15044. |
11 | 許雅涵 | Ya-Han Hsu | YHH | 第一作者,且唯一作者
第一作者,且唯一作者 第一作者 |
1) Tetrahedron Lett. 2021, 63, 152718.
2) J. Org. Chem. 2022, 87, 13308-13314. 3) Tetrahedron 2024, 162, 134090. |
12 | 王沛淩 | Pei-Ling Wang | PLW | 第一作者 | Tetrahedron 2023, 146, 133648. |
獲獎經歷
Nam eget dui. Etiam rhoncus. Maecenas tempus, tellus eget condimentum rhoncus.
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德國學術交流署DAAD與國科會-三明治計畫獎學金 2005-2006
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科技部特殊優秀人才獎勵(校內)-105、106學年度
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國科會補助大專院校研究獎勵 (校內) – 111年度
Selected Invited Lectures
Selected Invited Lectures (重要會議邀請演講)
Mar 29, 2024, 中國化學會年會, 淡江大學
“Radical Carbonyl Migration: Synthesis of L-Deoxysugars and Telbivudine (L-dT)”
Sep 16, 2023, 化學生科與物理跨領域交流會-台中高鐵站集思會議中心
“Synthetic application of radical functional group migration reactions”
Mar 12, 2022, 中國化學會年會, 臺灣師範大學
“Radicals in the Synthesis of L-Deoxysugars”
Jan 15, 2021, 劃時代的Reaxys 應用與未來藍圖-視訊會議
“Reaxys 應用於合成 L-去氧醣”
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”
實驗室出遊
圖片介紹
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