Citation: Wang Hao, Wu Pinru, Zhao Xiang, Zeng Jing, Wan Qian. Advances on Photo-Promoted Glycosylation Reactions[J]. Acta Chimica Sinica, ;2019, 77(3): 231-241. doi: 10.6023/A18100429 shu

Advances on Photo-Promoted Glycosylation Reactions

School of Pharmacy, Huazhong University of Science and Technology, Wuhan 430030

Corresponding author: Wan Qian, wanqian@hust.edu.cn
Received Date: 16 October 2018
Available Online: 25 March 2018
Fund Project: the National Natural Science Foundation of China 21472054the National Natural Science Foundation of China 21761132014the State Key Laboratory of Bio-organic and Natural Products Chemistry SKLBNPC13425Project supported by the National Natural Science Foundation of China (Nos. 21472054, 21761132014, 21772050, 21702068), the State Key Laboratory of Bio-organic and Natural Products Chemistry (No. SKLBNPC13425) and Wuhan Creative Talent Development Fundthe National Natural Science Foundation of China 21702068the National Natural Science Foundation of China 21772050

Figures(21)

Carbohydrates, along with proteins and nucleic acids are known as basic life substances, which not only are the energy source and structure material, but also play an extremely important role in many biochemical processes, such as molecules recognition, information transformation in cells, interactions in immune response, differentiation and apoptosis of cells, etc. Compared to proteins and nucleic acids, the synthesis of oligosaccharides in chemical or enzymatic ways is more difficult, due to their diversified and complicated structures. Recently photo especially visible light promoted organic synthesis has become one of the fastest growing fields in organic chemistry attributed to its environmental friendliness, easy availability and low cost. This chemistry has also been applied to the photo-mediated glycosylation reactions by using various light sources (ultraviolet, visible light), photosensitizers (or photocatalysts), and additives (oxidants, reductants etc.), which provides milder and more effective ways for oligosaccharide assembly. To help chemists understand this field, we briefly reviewed recent advances and potential applications of photo-mediated glycosylation reactions according to their types (e.g. light sources, photosensitizers). In this review, we also detailly described the mechanisms and highlighted the advantages and limitations of these reactions. In addition, the further prospects of this area are proposed.
- carbohydrates,
- glycosylation,
- photochemistry,
- photo catalysis,
- visible light promoted reaction
1. [1]
2. [2]
  Guo, Z.; Wang, L. Prog. Chem. 1995, 7, 10.
3. [3]
  Varki, A.; Cummings, R.-D.; Esko, J.-D.; Freeze, H.-H.; Stanley, P.; Bertozzi, C.-R.; Hart, G.-W.; Etzler, M.-E. Essential of Glycobiology, Cold Spring Harbor Laboratory Press, 2008, pp. 1~21.
4. [4]
  Chen, L.-Q.; Lai, D.; Song, Z.-W.; Zhao, X.-E.; Kong, F.-Z. Chin. J. Org. Chem. 2006, 26, 627.
5. [5]
  Fischer, E. Chem. Ber. 1893, 26, 2400. doi: 10.1002/(ISSN)1099-0682
6. [6]
  (a) Koenigs, W.; Knorr, E. Chem. Ber. 1901, 34, 957. (b) Schmidt, R. R.; Michel, J. Angew. Chem. 1980, 92, 763. (c) Geng, Y.; Zhang, L. -H.; Ye, X. -S. Chem. Commun. 2008, 5, 597. (d) Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580. (e) Tang, Y.; Li, J.; Zhu, Y.; Li, Y.; Yu, B. J. Am. Chem. Soc. 2013, 135, 18396.
7. [7]
  (a) Shu, P.; Xiao, X.; Zhao, Y.; Xu, Y.; Yao, W.; Tao, J.; Wang, H.; Yao, G.; Lu, Z.; Zeng, J.; Wan, Q. Angew. Chem.,Int. Ed. 2015, 54, 14432. (b) Xiao, X.; Zhao, Y.; Shu, P.; Zhao, X.; Liu, Y.; Sun, J.; Zhang, Q.; Zeng, J.; Wan, Q. J. Am. Chem. Soc. 2016, 138, 13402. (c) Hu, Y.; Yu, K.; Shi, L.-L.; Liu, L.; Sui, J.-J.; Liu, D.-Y.; Xiong, B.; Sun, J.-S. J. Am. Chem. Soc. 2017, 139, 12736. (d) Wang, H.-Y.; Simmons, C. J.; Blaszczyk, S. A.; Balzer, P. G.; Luo, R.; Duan, X.; Tang, W. Angew. Chem. , Int. Ed. 2017, 56, 15698. (e) Wadzinski, T. J.; Steinauer, A.; Hie, L.; Pelletier, G.; Schepartz, A.; Miller, S. J. Nature Chem. 2018, 10, 644.
8. [8]
9. [9]
  Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77. doi: 10.1126/science.1161976
10. [10]
  Ischay, M. A.; Anzovino, M. E.; Du, J.; Yoon, T. P. J. Am. Chem. Soc. 2008, 130, 12886. doi: 10.1021/ja805387f
11. [11]
  Nguyen, J. D.; D'Amato, E. M.; Narayanam, J. M. R.; Stephenson, C. R. J. Nat. Chem. 2012, 4, 854. doi: 10.1038/nchem.1452
12. [12]
  Xuan, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 6828. doi: 10.1002/anie.201200223
13. [13]
14. [14]
  Yamago, S.; Miyazoe, H.; Yoshida, J.-i. Tetrahedron Lett. 1999, 40, 2339. doi: 10.1016/S0040-4039(99)00181-1
15. [15]
  Nakanishi, M.; Takahashi, D.; Toshima, K. Org. Biomol. Chem. 2013, 11, 5079. doi: 10.1039/c3ob41143e
16. [16]
  Mao, R.-Z.; Guo, F.; Xiong, D.-C.; Li, Q.; Duan, J.; Ye, X.-S. Org. Lett. 2015, 17, 5606. doi: 10.1021/acs.orglett.5b02823
17. [17]
  Mao, R.-Z.; Xiong, D.-C.; Guo, F.; Li, Q.; Duan, J.; Ye, X.-S. Org. Chem. Front. 2016, 3, 737. doi: 10.1039/C6QO00021E
18. [18]
  Hashimoto, S.; Kurimoto, I.; Fujii, Y.; Noyori, R. J. Am. Chem. Soc. 1985, 107, 1427. doi: 10.1021/ja00291a062
19. [19]
  Griffin, G. W.; Bandara, N. C.; Clarke, M. A.; Tsang, W.-S.; Ga-regg, P.J.; Oscarson, S.; Silwanis, B. A. Heterocycles 1990, 30, 939. doi: 10.3987/COM-89-S89
20. [20]
  Furuta, T.; Takeuchi, K.; Iwamura, M. Chem. Commun. 1996, 147, 157.
21. [21]
  Cumpstey, I.; Crich, D. J.Carbohydr. Chem.2011, 30, 469. doi: 10.1080/07328303.2011.601533
22. [22]
  Iwata, R.; Uda, K.; Takahashi, D.; Toshima, K. Chem. Commun. 2014, 50, 10695. doi: 10.1039/C4CC04753B
23. [23]
  Kimura, T.; Eto, T.; Takahashi, D.; Toshima, K. Org. Lett. 2016, 18, 3190. doi: 10.1021/acs.orglett.6b01404
24. [24]
  (a) Balmond, E. I.; Coe, D. M.; Galan, M. C.; McGarrigle, E. M. Angew. Chem. , Int. Ed.2012, 51, 9152.(b) Balmond, E. I.; Benito-Alifonso, D.; Coe, D. M.; Alder, R. W.; McGarrigle, E. M.; Galan, M. C.Angew. Chem., Int. Ed.2014, 53, 8190.(c) Sau, A.; Williams, R.; Palo-Nieto, C.; Franconetti, A.; Medina, S.; Galan, M. C.Angew. Chem., Int. Ed.2017, 56, 3640. (d) Palo-Nieto, C.; Sau, A.; Galan, M. C. J. Am. Chem. Soc. 2017, 139, 14041.
25. [25]
  Zhao, G.; Wang, T. Angew. Chem., Int. Ed. 2018, 57, 6120. doi: 10.1002/anie.201800909
26. [26]
  Andrews, R. S.; Becker, J. J.; Gagné, M. R. Angew. Chem., Int. Ed. 2010, 49, 7274. doi: 10.1002/anie.v49:40
27. [27]
  Andrews, R. S.; Becker, J. J.; Gagné, M. R. Angew. Chem., Int. Ed. 2012, 51, 4140. doi: 10.1002/anie.201200593
28. [28]
  Spell, M.; Wang, X.; Wahba, A. E.; Conner, E.; Ragains, J. Carbohydr. Res. 2013, 369, 42. doi: 10.1016/j.carres.2013.01.004
29. [29]
  Wever, W. J.; Cinelli, M. A.; Bowers, A. A. Org. Lett. 2013, 15, 30. doi: 10.1021/ol302941q
30. [30]
  Yu, Y.; Xiong, D.-C.; Mao, R.-Z.; Ye, X.-S. J. Org. Chem. 2016, 8, 7134.
31. [31]
  Zhu, Q.; Gentry, E. C.; Knowles, R. R. Angew. Chem., Int. Ed. 2016, 55, 9969. doi: 10.1002/anie.201604619
32. [32]
  Wen, P.; Crich, D. Org. Lett. 2017, 19, 2402. doi: 10.1021/acs.orglett.7b00932
33. [33]
  Ye, H.; Xiao, C.; Zhou, Q.-Q.; Wang, P. G.; Xiao, W.-J. J. Org. Chem. 2018, 83, 13325. doi: 10.1021/acs.joc.8b02129
34. [34]
  (a) Arceo, E.; Jurberg, I. D.; Álvarez-Fernández, A.; Melchiorre, P. Nat. Chem. 2013, 5, 750.(b) Lima, C. G. S.; Lima, T. de M.; Duarte, M.; Jurberg, I. D.; Paixão, M. W.ACS Catal. 2016, 6, 1389.
35. [35]
  Spell, M. L.; Deveaux, K.; Bresnahan, C. G.; Bernard, B. L.; Sheffield, W.; Kumar, R.; Ragains, J. R. Angew. Chem., Int. Ed. 2016, 55, 6515. doi: 10.1002/anie.201601566
1. [1]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
2. [2]
  Xinyu Xu , Jiale Lu , Bo Su , Jiayi Chen , Xiong Chen , Sibo Wang . Steering charge dynamics and surface reactivity for photocatalytic selective methane oxidation to ethane over Au/Ti-CeO₂. Acta Physico-Chimica Sinica, 2025, 41(11): 100153-0. doi: 10.1016/j.actphy.2025.100153
3. [3]
  Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
4. [4]
  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
5. [5]
  Deyun Ma , Fenglan Liang , Qingquan Xue , Yanping Liu , Chunqiang Zhuang , Shijie Li . Interfacial engineering of Cd_0.5Zn_0.5S/BiOBr S-scheme heterojunction with oxygen vacancies for effective photocatalytic antibiotic removal. Acta Physico-Chimica Sinica, 2025, 41(12): 100190-0. doi: 10.1016/j.actphy.2025.100190
6. [6]
  Qin Li , Huihui Zhang , Huajun Gu , Yuanyuan Cui , Ruihua Gao , Wei-Lin Dai . In situ Growth of Cd_0.5Zn_0.5S Nanorods on Ti₃C₂ MXene Nanosheet for Efficient Visible-Light-Driven Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2025, 41(4): 100031-0. doi: 10.3866/PKU.WHXB202402016
7. [7]
  Chengxiao Zhao , Zhaolin Li , Dongfang Wu , Xiaofei Yang . SBA-15 templated covalent triazine frameworks for boosted photocatalytic hydrogen production. Acta Physico-Chimica Sinica, 2026, 42(1): 100149-0. doi: 10.1016/j.actphy.2025.100149
8. [8]
  Jianyin He , Liuyun Chen , Xinling Xie , Zuzeng Qin , Hongbing Ji , Tongming Su . Construction of ZnCoP/CdLa₂S₄ Schottky Heterojunctions for Enhancing Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(11): 2404030-0. doi: 10.3866/PKU.WHXB202404030
9. [9]
  Bowen Liu , Jianjun Zhang , Han Li , Bei Cheng , Chuanbiao Bie . MOF-derived ZnO/PANI S-scheme heterojunction for efficient photocatalytic phenol mineralization coupled with H₂O₂ generation. Acta Physico-Chimica Sinica, 2025, 41(10): 100121-0. doi: 10.1016/j.actphy.2025.100121
10. [10]
  Yadan Luo , Hao Zheng , Xin Li , Fengmin Li , Hua Tang , Xilin She . Modulating reactive oxygen species in O, S co-doped C₃N₄ to enhance photocatalytic degradation of microplastics. Acta Physico-Chimica Sinica, 2025, 41(6): 100052-0. doi: 10.1016/j.actphy.2025.100052
11. [11]
  Jingzhuo Tian , Chaohong Guan , Haobin Hu , Enzhou Liu , Dongyuan Yang . Waste plastics promoted photocatalytic H₂ evolution over S-scheme NiCr₂O₄/twinned-Cd_0.5Zn_0.5S homo-heterojunction. Acta Physico-Chimica Sinica, 2025, 41(6): 100068-0. doi: 10.1016/j.actphy.2025.100068
12. [12]
  Jiawei Hu , Kai Xia , Ao Yang , Zhihao Zhang , Wen Xiao , Chao Liu , Qinfang Zhang . Interfacial Engineering of Ultrathin 2D/2D NiPS₃/C₃N₅ Heterojunctions for Boosting Photocatalytic H₂ Evolution. Acta Physico-Chimica Sinica, 2024, 40(5): 2305043-0. doi: 10.3866/PKU.WHXB202305043
13. [13]
  Yuanqing Wang , Yusong Pan , Hongwu Zhu , Yanlei Xiang , Rong Han , Run Huang , Chao Du , Chengling Pan . Enhanced Catalytic Activity of Bi₂WO₆ for Organic Pollutants Degradation under the Synergism between Advanced Oxidative Processes and Visible Light Irradiation. Acta Physico-Chimica Sinica, 2024, 40(4): 2304050-0. doi: 10.3866/PKU.WHXB202304050
14. [14]
  Xin Zhou , Zhi Zhang , Yun Yang , Shuijin Yang . A Study on the Enhancement of Photocatalytic Performance in C/Bi/Bi₂MoO₆ Composites by Ferroelectric Polarization: A Recommended Comprehensive Chemical Experiment. University Chemistry, 2024, 39(4): 296-304. doi: 10.3866/PKU.DXHX202310008
15. [15]
  Xinyu Yin , Haiyang Shi , Yu Wang , Xuefei Wang , Ping Wang , Huogen Yu . Spontaneously Improved Adsorption of H₂O and Its Intermediates on Electron-Deficient Mn^(3+δ)+ for Efficient Photocatalytic H₂O₂ Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312007-0. doi: 10.3866/PKU.WHXB202312007
16. [16]
  Changjun You , Chunchun Wang , Mingjie Cai , Yanping Liu , Baikang Zhu , Shijie Li . Improved Photo-Carrier Transfer by an Internal Electric Field in BiOBr/N-rich C₃N₅ 3D/2D S-Scheme Heterojunction for Efficiently Photocatalytic Micropollutant Removal. Acta Physico-Chimica Sinica, 2024, 40(11): 2407014-0. doi: 10.3866/PKU.WHXB202407014
17. [17]
  Tongyan Yu , Pan Xu . Visible-Light Photocatalyzed Radical Rearrangement Reaction. University Chemistry, 2025, 40(7): 169-176. doi: 10.12461/PKU.DXHX202409070
18. [18]
  Yongxin LIU , Xingchen LI , Hongjia LIU , Danni LI , Tao ZHANG , Xi CHEN . Enhancement effect of Fe₃O₄ conversion to MIL-100(Fe) on activation of persulfate for degradation of antibiotic. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2503-2513. doi: 10.11862/CJIC.20250169
19. [19]
  Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
20. [20]
  Kun WANG , Wenrui LIU , Peng JIANG , Yuhang SONG , Lihua CHEN , Zhao DENG . Hierarchical hollow structured BiOBr-Pt catalysts for photocatalytic CO₂ reduction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1270-1278. doi: 10.11862/CJIC.20240037

Get Citation

PDF

XML

Metrics

PDF Downloads(94)
Abstract views(4659)
HTML views(922)

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