Citation: Wu Yong, Ye Xin-Shan. Recent Advances in Chemical Synthesis of Polysaccharides[J]. Acta Chimica Sinica, ;2019, 77(7): 581-597. doi: 10.6023/A19040128 shu

Recent Advances in Chemical Synthesis of Polysaccharides

Wu Yong ,
Ye Xin-Shan ^,

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191

Corresponding author: Ye Xin-Shan, xinshan@bjmu.edu.cn
Received Date: 11 April 2019
Available Online: 6 July 2019
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21738001)the National Natural Science Foundation of China 21738001

Figures(22)

Polysaccharides are a class of bio-macromolecules with highly complex structures that are widely found in living organisms such as microorganisms, plants and animals. Polysaccharides serve not only as structural components and energy sources of cells, but also as important signaling molecules which are involved in many key biological processes. Studies on polysaccharide-mediated biological processes require access to structurally defined molecules, which approach the size and complexity of those found in nature, but naturally-occurring polysaccharides usually exist in microheterogeneous forms, making it difficult or even impossible to isolate pure polysaccharides from natural sources in most cases. Chemical synthesis represents a reliable solution to this problem, which can provide polysaccharide samples with defined chemical structures for functional studies and even a library of analogs of natural glycans for structure-activity relationship investigations. But unlike oligonucleotides and peptides, which can already be obtained by automated synthesizers in a very short of time, the chemical synthesis of glycans remains a great challenge for synthetic chemists. The major challenge for glycan synthesis lies in the need to handle both stereo-and regio-chemistry in the construction of each glycosyl linkage, and the extensive protecting-group manipulations as well as much intermediate separation make it a tedious and time-consuming process. Over the past decades, carbohydrate chemists have developed many glycosylation reactions. A series of strategies for glycan assembly have been also established. The advances in both synthetic methods and strategies have significantly increased the synthetic efficiency of carbohydrate molecules, and many great accomplishments in the field of polysaccharide synthesis have been witnessed in recent decades. Some representative methods and strategies, and their successful applications in the chemical synthesis of complex polysaccharides are summarized in this review.
- polysaccharide,
- chemical synthesis,
- glycosylation method,
- synthetic strategy
1. [1]
  Varki, A. Glycobiology 1993, 3, 97. doi: 10.1093/glycob/3.2.97
2. [2]
  Krasnova, L.; Wong, C.-H. Annu. Rev. Biochem. 2016, 85, 599. doi: 10.1146/annurev-biochem-060614-034420
3. [3]
  Boltje, T. J.; Buskas, T.; Boons, G.-J. Nat. Chem. 2009, 1, 611. doi: 10.1038/nchem.399
4. [4]
  Seeberger, P. H.; Werz, D. B. Nature 2007, 446, 1046. doi: 10.1038/nature05819
5. [5]
6. [6]
  Bertozzi, C. R.; Kiessling, L. L. Science 2001, 291, 2357. doi: 10.1126/science.1059820
7. [7]
  Gabius, H.-J. The Sugar Code:Fundamentals of Glycosciences, John Wiley & Sons, New Jersey, 2011.
8. [8]
  Tanaka, H.; Kawai, T.; Adachi, Y.; Hanashima, S.; Yamaguchi, Y.; Ohno, N.; Takahashi, T. Bioorg. Med. Chem. 2012, 20, 3898. doi: 10.1016/j.bmc.2012.04.017
9. [9]
  Petitou, M.; Duchaussoy, P.; Driguez, P.-A.; Hérault, J.-P.; Lormeau, J.-C.; Herbert, J.-M. Bioorg. Med. Chem. Lett. 1999, 9, 1155. doi: 10.1016/S0960-894X(99)00155-9
10. [10]
  Wang, L.; Feng, S.; An, L.; Gu, G.; Guo, Z. J. Org. Chem. 2015, 80, 10060. doi: 10.1021/acs.joc.5b01686
11. [11]
  (a) Zhu, X.; Schmidt, R. R. Angew. Chem. Int. Ed. 2009, 48, 1900; (b) Hsu, C.-H.; Hung, S.-C.; Wu, C.-Y.; Wong, C.-H. Angew. Chem. Int. Ed. 2011, 50, 11872; (c) Seeberger, P. H. Acc. Chem. Res. 2015, 48, 1450; (d) Kulkarni, S. S.; Wang, C.-C.; Sabbavarapu, N. M.; Podilapu, A. R.; Liao, P.-H.; Hung, S.-C. Chem. Rev. 2018, 118, 8025.
12. [12]
  Michael, A. Am. Chem. J. 1879, 1, 305. doi: 10.1021/ja02151a603
13. [13]
  Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. doi: 10.1021/cr00020a006
14. [14]
  (a) Garcia, B. A.; Poole, J. L.; Gin, D. Y. J. Am. Chem. Soc. 1997, 119, 7597; (b) Garcia, B. A.; Gin, D. Y. J. Am. Chem. Soc. 2000, 122, 4269.
15. [15]
  (a) Schmidt, R. R.; Michel, J. Angew. Chem. Int. Ed. 1980, 19, 731; (b) Schmidt, R. R. Angew. Chem. Int. Ed. 1986, 25, 212.
16. [16]
  (a) Codée, J. D. C.; Litjens, R. E. J. N.; van den Bos, L. J.; Overkleeft, H. S.; van der Marel, G. A. Chem. Soc. Rev. 2005, 34, 769; (b) Lian, G.; Zhang, X.; Yu, B. Carbohydr. Res. 2015, 403, 13.
17. [17]
  Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraser-Reid, B. J. Am. Chem. Soc. 1988, 110, 5583. doi: 10.1021/ja00224a060
18. [18]
  Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem. Int. Ed. 1996, 35, 1380. doi: 10.1002/(ISSN)1521-3773
19. [19]
  Plante, O. J.; Palmacci, E. R.; Andrade, R. B.; Seeberger, P. H. J. Am. Chem. Soc.2001, 123, 9545. doi: 10.1021/ja016227r
20. [20]
  Yu, B. Acc. Chem. Res. 2018, 51, 507. doi: 10.1021/acs.accounts.7b00573
21. [21]
  Koenigs, W.; Knorr, E. Ber. Dtsch. Chem. Ges. 1901, 34, 957. doi: 10.1002/(ISSN)1099-0682
22. [22]
  Zemplén, G.; Gerecs, A. Ber. Dtsch. Chem. Ges. 1930, 63, 2720. doi: 10.1002/cber.v63:10
23. [23]
  Helferich, B.; Wedemeyer, K. F. Justus Liebigs Ann. Chem. 1949, 563, 139. doi: 10.1002/(ISSN)1099-0690
24. [24]
  Igarashi, K.; Irisawa, J.; Honma, T. Carbohydr. Res. 1975, 39, 213. doi: 10.1016/S0008-6215(00)86131-5
25. [25]
  Kronzer, F. J.; Schuerch, C. Carbohydr. Res. 1973, 27, 379. doi: 10.1016/S0008-6215(00)81320-8
26. [26]
  Wulff, G.; Röhle, G.; Krüger, W. Chem. Ber. 1972, 105, 1097. doi: 10.1002/(ISSN)1099-0682
27. [27]
  Yamada, H.; Hayashi, T. Carbohydr. Res. 2002, 337, 581. doi: 10.1016/S0008-6215(02)00029-0
28. [28]
  Bernstein, S.; Conrow, R. B. J. Org. Chem. 1971, 36, 863. doi: 10.1021/jo00806a001
29. [29]
  Nishizawa, M.; Garcia, D. M.; Shin, T.; Yamada, H. Chem. Pharm. Bull. 1993, 41, 784. doi: 10.1248/cpb.41.784
30. [30]
  Mukaiyama, T.; Murai, Y.; Shoda, S. Chem. Lett. 1981, 10, 431. doi: 10.1246/cl.1981.431
31. [31]
  Mukaiyama, T.; Hashimoto, Y.; Shoda, S. Chem. Lett. 1983, 12, 935. doi: 10.1246/cl.1983.935
32. [32]
  Matsumoto, T.; Maeta, H.; Suzuki, K. Tetrahedron Lett. 1988, 29, 3567. doi: 10.1016/0040-4039(88)85294-8
33. [33]
  Hashimoto, S.; Hayashi, M.; Noyori, R. Tetrahedron Lett. 1984, 25, 1379. doi: 10.1016/S0040-4039(01)80163-5
34. [34]
  Mukaiyama, T.; Jona, H.; Takeuchi, K. Chem. Lett. 2000, 29, 696. doi: 10.1246/cl.2000.696
35. [35]
  Zhu, X.; Schmidt, R. R. Angew. Chem., Int. Ed. 2009, 48, 1900. doi: 10.1002/anie.v48:11
36. [36]
  El-Badry, M. H.; Gervay-Hague, J. Tetrahedron Lett. 2005, 46, 6727. doi: 10.1016/j.tetlet.2005.07.129
37. [37]
  (a) Lam, S. N.; Gervay-Hague, J. Carbohydr. Res. 2002, 337, 1953; (b) Lam, S. N.; Gervay-Hague, J. Org. Lett. 2002, 4, 2039; (c) Lam, S. N.; Gervay-Hague, J. J. Org. Chem. 2005, 70, 2387.
38. [38]
  Sun, L.; Wu, X.; Xiong, D.-C.; Ye, X.-S. Angew. Chem. Int. Ed. 2016, 55, 8041. doi: 10.1002/anie.201600142
39. [39]
  Park, Y.; Harper, K. C.; Kuhl, N.; Kwan, E. E.; Liu, R. Y.; Jacobsen, E. N. Science 2017, 355, 162. doi: 10.1126/science.aal1875
40. [40]
  Schmidt, R. R.; Toepfer, A. Tetrahedron Lett. 1991, 32, 3353. doi: 10.1016/S0040-4039(00)92704-7
41. [41]
  Yu, B.; Tao, H. Tetrahedron Lett. 2001, 42, 2405. doi: 10.1016/S0040-4039(01)00157-5
42. [42]
  Ferrier, R. J.; Hay, R. W.; Vethaviyasar, N. Carbohydr. Res. 1973, 27, 55. doi: 10.1016/S0008-6215(00)82424-6
43. [43]
  Veeneman, G. H.; Van Leeuwen, S. H.; Van Boom, J. H. Tetrahedron Lett. 1990, 31, 1331. doi: 10.1016/S0040-4039(00)88799-7
44. [44]
  Konradsson, P.; Udodong, U. E.; Fraser-Reid, B. Tetrahedron Lett. 1990, 31, 4313. doi: 10.1016/S0040-4039(00)97609-3
45. [45]
  Andersson, F.; Fúgedi, P.; Garegg, P. J.; Nashed, M. Tetrahedron Lett. 1986, 27, 3919. doi: 10.1016/S0040-4039(00)83917-9
46. [46]
  Martichonok, V.; Whitesides, G. M. J. Org. Chem. 1996, 61, 1702. doi: 10.1021/jo951711w
47. [47]
  Crich, D.; Smith, M. J. Am. Chem. Soc. 2001, 123, 9015. doi: 10.1021/ja0111481
48. [48]
  Codée, J. D. C.; Litjens, R. E. J. N.; den Heeten, R.; Overkleeft, H. S.; van Boom, J. H.; van der Marel, G. A. Org. Lett. 2003, 5, 1519. doi: 10.1021/ol034312t
49. [49]
  Wang, C.; Wang, H.; Huang, X.; Zhang, L.-H.; Ye, X.-S. Synlett 2006, 2846.
50. [50]
  Marra, A.; Mallet, J. M.; Amatore, C.; Sinaÿ, P. Synlett 1990, 572. doi: 10.1055/s-1990-22045
51. [51]
  (a) Mitsudo, K.; Kawaguchi, T.; Miyahara, S.; Matsuda, W.; Kuroboshi, M.; Tanaka, H. Org. Lett. 2005, 7, 4649; (b) Nokami, T.; Shibuya, A.; Tsuyama, H.; Suga, S.; Bowers, A. A.; Crich, D.; Yoshida, J. I. J. Am. Chem. Soc. 2007, 129, 10922.
52. [52]
53. [53]
  Goswami, M.; Ellern, A.; Pohl, N. L. B. Angew. Chem. Int. Ed. 2013, 52, 8441. doi: 10.1002/anie.v52.32
54. [54]
  Yamada, H.; Harada, T.; Miyazaki, H.; Takahashi, T. Tetrahedron Lett. 1994, 35, 3979. doi: 10.1016/S0040-4039(00)76718-9
55. [55]
  Zhang, Z.; Ollmann, I. R.; Ye, X.-S.; Wischnat, R.; Baasov, T.; Wong, C.-H. J. Am. Chem. Soc. 1999, 121, 734. doi: 10.1021/ja982232s
56. [56]
  Huang, X.; Huang, L.; Wang, H.; Ye, X.-S. Angew. Chem Int. Ed. 2004, 43, 5221. doi: 10.1002/(ISSN)1521-3773
57. [57]
  Plante, O. J.; Palmacci, E. R.; Seeberger, P. H. Science 2001, 291, 1523. doi: 10.1126/science.1057324
58. [58]
  Tanaka, H.; Adachi, M.; Tsukamoto, H.; Ikeda, T.; Yamada, H.; Takahashi, T. Org. Lett. 2002, 4, 4213. doi: 10.1021/ol020150+
59. [59]
  Yu, B.; Yu, H.; Hui, Y.; Han, X. Tetrahedron Lett. 1999, 40, 8591. doi: 10.1016/S0040-4039(99)01839-0
60. [60]
  Wang, P.; Lee, H.; Fukuda, M.; Seeberger, P. H. Chem. Commun. 2007, 1963.
61. [61]
  Vohra, Y.; Buskas, T.; Boons, G.-J. J. Org. Chem. 2009, 74, 6064. doi: 10.1021/jo901135k
62. [62]
  (a) Hsu, C.-H.; Chu, K. C.; Lin, Y. S.; Han, J. L.; Peng, Y. S.; Ren, C. T.; Wong, C.-H. Chem. Eur. J. 2010, 16, 1754; (b) Tanaka, H.; Tateno, Y.; Nishiura, Y.; Takahashi, T. Org. Lett. 2008, 10, 5597; (c) Tanaka, H.; Adachi, M.; Takahashi, T. Chem. Eur. J. 2005, 11, 849.
63. [63]
  (a) Dinkelaar, J.; Gold, H.; Overkleeft, H. S.; Codée, J. D.; van der Marel, G. A. J. Org. Chem. 2009, 74, 4208; (b) Hu, Y. P.; Lin, S. Y.; Huang, C. Y.; Zulueta, M. M. L.; Liu, J. Y.; Chang, W.; Hung, S.-C. Nat. Chem. 2011, 3, 557.
64. [64]
  Sarkar, S.; Dutta, S.; Das, G.; Sen, A. K. Tetrahedron 2011, 67, 4118. doi: 10.1016/j.tet.2011.03.109
65. [65]
  Burkhart, F.; Zhang, Z.; Wacowich-Sgarbi, S.; Wong, C.-H. Angew. Chem. Int. Ed. 2001, 40, 1274. doi: 10.1002/(ISSN)1521-3773
66. [66]
  Tsai, B. L.; Han, J. L.; Ren, C. T.; Wu, C.-Y.; Wong, C.-H. Tetrahedron Lett. 2011, 52, 2132. doi: 10.1016/j.tetlet.2010.11.055
67. [67]
  Mong, K. K. T.; Wong, C.-H. Angew. Chem. Int. Ed. 2002, 41, 4087. doi: 10.1002/1521-3773(20021104)41:21<4087::AID-ANIE4087>3.0.CO;2-X
68. [68]
  Lee, J. C.; Wu, C.-Y.; Apon, J. V.; Siuzdak, G.; Wong, C.-H. Angew. Chem. Int. Ed. 2006, 45, 2753. doi: 10.1002/(ISSN)1521-3773
69. [69]
  Mong, T. K. K.; Lee, H. K.; Durón, S. G.; Wong, C.-H. PNAS 2003, 100, 797. doi: 10.1073/pnas.0337590100
70. [70]
  Polat, T.; Wong, C.-H. J. Am. Chem. Soc. 2007, 129, 12795. doi: 10.1021/ja073098r
71. [71]
  Hsu, Y.; Lu, X. A.; Zulueta, M. M. L.; Tsai, C. M.; Lin, K. I.; Hung, S.-C.; Wong, C.-H. J. Am. Chem. Soc. 2012, 134, 4549. doi: 10.1021/ja300284x
72. [72]
  Wang, Z.; Zhou, L.; El-Boubbou, K.; Ye, X.-S.; Huang, X. J. Org. Chem. 2007, 72, 6409. doi: 10.1021/jo070585g
73. [73]
  Li, Q.; Guo, Z. Org. Lett. 2017, 19, 6558. doi: 10.1021/acs.orglett.7b03275
74. [74]
  Huang, L.; Huang, X. Chem. Eur. J. 2007, 13, 529. doi: 10.1002/(ISSN)1521-3765
75. [75]
  Miermont, A.; Zeng, Y.; Jing, Y.; Ye, X.-S.; Huang, X. J. Org. Chem. 2007, 72, 8958. doi: 10.1021/jo701694k
76. [76]
  Wang, Z.; Xu, Y.; Yang, B.; Tiruchinapally, G.; Sun, B.; Liu, R.; Huang, X. Chem. Eur. J. 2010, 16, 8365. doi: 10.1002/chem.v16:28
77. [77]
  Sun, B.; Srinivasan, B.; Huang, X. Chem. Eur. J. 2008, 14, 7072. doi: 10.1002/chem.v14:23
78. [78]
  Wang, Y.-S.; Wu, Y.; Xiong, D.-C.; Ye, X.-S. Chin. J. Chem. 2019, 37, 42. doi: 10.1002/cjoc.v37.1
79. [79]
  (a) Gao, J.; Guo, Z. J. Org. Chem. 2013, 78, 12717; (b) Gao, J.; Liao, G.; Wang, L.; Guo, Z. Org. Lett. 2014, 16, 988; (c) Gao, J.; Guo, Z. Org. Lett. 2016, 18, 5552. (d) Wang, D.; Xiong, D.-C.; Ye, X.-S. Chin. Chem. Lett. 2018, 29, 1340; (e) Wu, Y.; Xiong, D.-C.; Chen, S.-C.; Wang, Y.-S.; Ye, X.-S. Nat. Commun. 2017, 8, 14851.
80. [80]
  Werz, D. B.; Castagner, B.; Seeberger, P. H. J. Am. Chem. Soc. 2007, 129, 2770. doi: 10.1021/ja069218x
81. [81]
  Routenberg, L. K.; Seeberger, P. H. Angew. Chem. Int. Ed. 2004, 43, 602. doi: 10.1002/(ISSN)1521-3773
82. [82]
  Ratner, D. M.; Swanson, E. R.; Seeberger, P. H. Org. Lett. 2003, 5, 4717. doi: 10.1021/ol035887t
83. [83]
  Codée, J. D. C.; Kröck, L.; Castagner, B.; Seeberger, P. H. Chem. Eur. J. 2008, 14, 3987. doi: 10.1002/chem.v14:13
84. [84]
  (a) Walvoort, M. T. C.; Volbeda, A. G.; Reintjens, N. R. M.; van den Elst, H.; Plante, O. J.; Overkleeft, H. S.; Codée, J. D. Org. Lett. 2012, 14, 3776; (b) Hahm, H. S.; Broecker, F.; Kawasaki, F.; Mietzsch, M.; Heilbronn, R.; Fukuda, M.; Seeberger, P. H. Chem 2017, 2, 114.
85. [85]
  Hewitt, M. C.; Snyder, D. A.; Seeberger, P. H. J. Am. Chem. Soc. 2002, 124, 13434. doi: 10.1021/ja027538k
86. [86]
  Matsuzaki, Y.; Ito, Y.; Nakahara, Y.; Ogawa, T. Tetrahedron Lett. 1993, 34, 1061. doi: 10.1016/S0040-4039(00)77492-2
87. [87]
  Hansen, S. U.; Miller, G. J.; Cliff, M. J.; Jayson, G. C.; Gardiner, J. M. Chem. Sci. 2015, 6, 6158. doi: 10.1039/C5SC02091C
88. [88]
  Li, A.; Kong, F. Bioorg. Med. Chem. 2005, 13, 839. doi: 10.1016/j.bmc.2004.10.035
89. [89]
  Pozsgay, V. Angew. Chem. Int. Ed. 1998, 37, 138. doi: 10.1002/(ISSN)1521-3773
90. [90]
  Pozsgay, V.; Chu, C.; Pannell, L.; Wolfe, J.; Robbins, J. B.; Schneerson, R. PNAS 1999, 96, 5194. doi: 10.1073/pnas.96.9.5194
91. [91]
  Pozsgay, V. Tetrahedron:Asymmetry 2000, 11, 151. doi: 10.1016/S0957-4166(99)00553-4
92. [92]
  Joe, M.; Bai, Y.; Nacario, R. C.; Lowary, T. L. J. Am. Chem. Soc. 2007, 129, 9885. doi: 10.1021/ja072892+
93. [93]
  Ishiwata, A.; Ito, Y. J. Am. Chem. Soc. 2011, 133, 2275. doi: 10.1021/ja109932t
94. [94]
  Thadke, S. A.; Mishra, B.; Islam, M.; Pasari, S.; Manmode, S.; Rao, B. V.; Hotha, S. Nat. Commun. 2017, 8, 14019. doi: 10.1038/ncomms14019
95. [95]
  Pasari, S.; Manmode, S.; Walke, G.; Hotha, S. Chem. Eur. J. 2018, 24, 1128. doi: 10.1002/chem.201704009
96. [96]
  Mishra, B.; Neralkar, M.; Hotha, S. Angew. Chem. Int. Ed. 2016, 55, 7786. doi: 10.1002/anie.201511695
97. [97]
  Fraser-Reid, B.; Lu, J.; Jayaprakash, K. N.; Lopez, J. C. Tetrahedron:Asymmetry 2006, 17, 2449. doi: 10.1016/j.tetasy.2006.09.008
98. [98]
  Islam, M.; Shinde, G. P.; Hotha, S. Chem. Sci. 2017, 8, 2033. doi: 10.1039/C6SC04866H
99. [99]
  Calin, O.; Eller, S.; Seeberger, P. H. Angew. Chem. Int. Ed. 2013, 52, 5862. doi: 10.1002/anie.201210176
100. [100]
  Naresh, K.; Schumacher, F.; Hahm, H. S.; Seeberger, P. H. Chem. Commun. 2017, 53, 9085. doi: 10.1039/C7CC04380E
101. [101]
  Yu, Y.; Kononov, A.; Delbianco, M.; Seeberger, P. H. Chem. Eur. J. 2018, 24, 6075. doi: 10.1002/chem.v24.23
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2. [2]
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  Yufang GAO , Nan HOU , Yaning LIANG , Ning LI , Yanting ZHANG , Zelong LI , Xiaofeng LI . Nano-thin layer MCM-22 zeolite: Synthesis and catalytic properties of trimethylbenzene isomerization reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1079-1087. doi: 10.11862/CJIC.20240036
14. [14]
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15. [15]
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沈阳化工大学材料科学与工程学院沈阳 110142