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

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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
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