Home

Citation: Yuan Haolin, Wu Yubao, Yang Yang, He Wanlin, Zhao Peipei, Wang Ying, Cai Yan. An Improved Synthetic Approach to Mannosidase Inhibitor-Kifunensine[J]. Chemistry, ;2019, 82(11): 1013-1018. shu

An Improved Synthetic Approach to Mannosidase Inhibitor-Kifunensine

Yuan Haolin ² ,
Wu Yubao ² ,
Yang Yang ² ,
He Wanlin ¹ ,
Zhao Peipei ^1,, ,
Wang Ying ^3,, ,
Cai Yan ^1,,

1.
Tianjin International Joint Academy of Biomedicine, Tianjin 300457
2.
College of Pharmacy, Nankai University, Tianjin 300071
3.
Tianjin Crops Research Institute, Tianjin Academy of Agricultural Sciences, Tianjin 300384

Corresponding author: Zhao Peipei, zhaopp_89@163.com Wang Ying, wangying1412@163.com Cai Yan, caiyan_86@163.com
Received Date: 5 June 2019
Accepted Date: 26 August 2019

Figures(2)

Kifunensine is an alkaloid isolated from actinomycetes named Kitasatosporia kifunense. It is a neutral and stable compound, and an effective inhibitor of mannosidase I. Kifunensine is currently widely used in the field of drug discovery and has very high commercial value. However, the synthesis of Kifunensine is difficult, and there are problems such as low yield and high synthesis cost. In this paper, the cheap and easily available L-gulonic acid-γ-lactone was used as a raw material to obtain Kifunensine through a series of reactions. One-pot synthesis protocol has been applied in some of the synthetic steps, which makes the operation simple, and the total yield is 4.8%. This novel method provides a probability to the large scale synthesis of Kifunensine.
- Kifunensine,
- Mannosidase inhibitor,
- Improved synthetic method
1. [1]
  M Iwami, O Nakayama, H Terano et al. J. Antibiot., 1987, 40(5): 612~622.
2. [2]
  A Herscovics. Biochim. Biophys. Acta, 1999, 1473: 96~107.
3. [3]
  H Kayakiri, S Takase, T Shibata et al. J. Org. Chem., 1989, 54: 4015~4016.
4. [4]
  H Kayakiri, S Takase, T Shibata et al. Chem. Pharm. Bull. 1991, 39(6): 1378~1381.
5. [5]
6. [6]
7. [7]
8. [8]
  K W Hering, K Karaveg, K W Moremen. J. Org. Chem., 2005, 70: 9892~9904.
1. [1]
  Yihui Song , Shangshang Qin , Kai Wu , Chengyun Jin , Bin Yu . 生物化学在高水平创新型药学人才培养中的交叉融合应用——以去甲基化酶LSD1抑制剂的活性评价为例. University Chemistry, 2025, 40(6): 341-352. doi: 10.12461/PKU.DXHX202406018
2. [2]
  Qingying Gao , Tao Luo , Jianyuan Su , Chaofan Yu , Jiazhu Li , Bingfei Yan , Wenzuo Li , Zhen Zhang , Yi Liu . Refinement and Expansion of the Classic Cinnamic Acid Synthesis Experiment. University Chemistry, 2024, 39(5): 243-250. doi: 10.3866/PKU.DXHX202311074
3. [3]
  Wanmin Cheng , Juan Du , Peiwen Liu , Yiyun Jiang , Hong Jiang . Photoinitiated Grignard Reagent Synthesis and Experimental Improvement in Triphenylmethanol Preparation. University Chemistry, 2024, 39(5): 238-242. doi: 10.3866/PKU.DXHX202311066
4. [4]
  Jiaojiao Yu , Bo Sun , Na Li , Cong Wen , Wei Li . Improvement of Classical Organic Experiment Based on the “Reverse-Step Optimization Method”: Taking Synthesis of Ethyl Acetate as an Example. University Chemistry, 2025, 40(3): 333-341. doi: 10.12461/PKU.DXHX202405177
5. [5]
  Li Jiang , Changzheng Chen , Yang Su , Hao Song , Yanmao Dong , Yan Yuan , Li Li . Electrochemical Synthesis of Polyaniline and Its Anticorrosive Application: Improvement and Innovative Design of the “Chemical Synthesis of Polyaniline” Experiment. University Chemistry, 2024, 39(3): 336-344. doi: 10.3866/PKU.DXHX202309002
6. [6]
  Yukun Chang , Haoqin Huang , Baolei Wang . Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment. University Chemistry, 2024, 39(4): 322-328. doi: 10.3866/PKU.DXHX202309095
7. [7]
  Zhuoya WANG , Le HE , Zhiquan LIN , Yingxi WANG , Ling LI . Multifunctional nanozyme Prussian blue modified copper peroxide: Synthesis and photothermal enhanced catalytic therapy of self-provided hydrogen peroxide. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2445-2454. doi: 10.11862/CJIC.20240194
8. [8]
  Lanjun Cheng , Xinyuan Wang , Jie An , Xiang Wu , Chengfeng Zhu , Yanming Fu , Yougui Li . Improvement of the Resolution Experiment of Racemic Tartaric Acid. University Chemistry, 2025, 40(7): 277-285. doi: 10.12461/PKU.DXHX202408010
9. [9]
  Xiuyun Wang , Jiashuo Cheng , Yiming Wang , Haoyu Wu , Yan Su , Yuzhuo Gao , Xiaoyu Liu , Mingyu Zhao , Chunyan Wang , Miao Cui , Wenfeng Jiang . Improvement of Sodium Ferric Ethylenediaminetetraacetate (NaFeEDTA) Iron Supplement Preparation Experiment. University Chemistry, 2024, 39(2): 340-346. doi: 10.3866/PKU.DXHX202308067
10. [10]
  Liuchuang Zhao , Wenbo Chen , Leqian Hu . Discussion on Improvement of Teaching Contents about Common Evaluation Parameters in Analytical Chemistry. University Chemistry, 2024, 39(2): 379-391. doi: 10.3866/PKU.DXHX202308079
11. [11]
  Yongming Guo , Jie Li , Chaoyong Liu . Green Improvement and Educational Design in the Synthesis and Characterization of Silver Nanoparticles. University Chemistry, 2024, 39(3): 258-265. doi: 10.3866/PKU.DXHX202309057
12. [12]
  Shuying Zhu , Shuting Wu , Ou Zheng . Improvement and Expansion of the Experiment for Determining the Rate Constant of the Saponification Reaction of Ethyl Acetate. University Chemistry, 2024, 39(4): 107-113. doi: 10.3866/PKU.DXHX202310117
13. [13]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
14. [14]
  Jiayu Tang , Jichuan Pang , Shaohua Xiao , Xinhua Xu , Meifen Wu . Improvement for Measuring Transference Numbers of Ions by Moving-Boundary Method. University Chemistry, 2024, 39(5): 193-200. doi: 10.3866/PKU.DXHX202311021
15. [15]
  Ruitong Zhang , Zhiqiang Zeng , Xiaoguang Zhang . Improvement of Ethyl Acetate Saponification Reaction and Iodine Clock Reaction Experiments. University Chemistry, 2024, 39(8): 197-203. doi: 10.3866/PKU.DXHX202312004
16. [16]
  Tong Zhou , Jun Li , Zitian Wen , Yitian Chen , Hailing Li , Zhonghong Gao , Wenyun Wang , Fang Liu , Qing Feng , Zhen Li , Jinyi Yang , Min Liu , Wei Qi . Experiment Improvement of “Redox Reaction and Electrode Potential” Based on the New Medical Concept. University Chemistry, 2024, 39(8): 276-281. doi: 10.3866/PKU.DXHX202401005
17. [17]
  Jiangjuan Shao , Xuan Li , Jingdan Weng , Xiaolei Chen , Fei Xu , Yulu Ma , Nianguang Li , Shizhong Zheng . Improvement in the Experimental Teaching Design of Physical and Chemical Identification and Quantification of Mineral Drugs. University Chemistry, 2024, 39(10): 137-142. doi: 10.3866/PKU.DXHX202312079
18. [18]
  Hongmei Chai , Yixia Ren , Xiangyang Hou , Long Tang , Jiawei Xie . 智能手机光传感的“丙酮碘化反应”实验改进. University Chemistry, 2025, 40(6): 193-200. doi: 10.12461/PKU.DXHX202407086
19. [19]
  Yan Li , Fei Ding , Jielun Yan , Qingyang Zhou , Zhe Wang , Yifan Shi , Jing Wang , Anna Tang . Improving Instrumental Analytical Chemistry Laboratory Teaching: Developing a Bilingual Classroom to Cultivate Innovative Talents. University Chemistry, 2025, 40(7): 83-89. doi: 10.12461/PKU.DXHX202409059
20. [20]
  Shahua Huang , Xiaoming Guo , Lin Lin , Guangping Chang , Sheng Han , Zuxin Zhou . Application of “Integration of Industry and Education” in Engineering Chemistry: Improvement of the Pesticide Fipronil Production. University Chemistry, 2024, 39(3): 199-204. doi: 10.3866/PKU.DXHX202309064

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(1090)
HTML views(200)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return