Articles

Progress in the Synthesis of Sialic Acid Derivatives

  • Wang Ruyi ,
  • Zhang Shu ,
  • Tan Yanhong ,
  • Hong Weiyao ,
  • Cheng Bo ,
  • Chen Qingxin ,
  • Zhu Yuntao ,
  • Feng Lianshun
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  • a Beijing National Laboratory for Molecular Sciences, Department of Chemical Biology, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871;
    b Pony Testing Co., Ltd., Beijing 100080;
    c School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen 518055

Received date: 2013-09-23

  Revised date: 2013-11-10

  Online published: 2013-12-06

Supported by

Project supported by the Shenzhen Strategic Emerging Industrial Development Funds (No. JCYJ20130329174913512), and the China Postdoctoral Science Foundation (No. 2013M540013).

Abstract

Sialic acids, a family of more than 50 members of α-keto acidic monosaccharides with a 9-carbon backbone, are widely distributed in mammalian organisms in the form of glycolipids or glycoproteins. It is the most important monosaccharide appeared on the surface of cells of vertebrates. Nowadays, thousands of unnatural sialic acid derivatives have been synthesized for molecular imaging due to various modifiable sites in the sialic acid structure. However, metabolic oligosaccharide engineering (MOE), is still locating at its preliminary stage and requiring perfection urgently. Here, the research progress in the synthesis of sialic acid derivatives is reviewed.

Key words: sialic acid; synthesis; progress

Cite this article

Wang Ruyi , Zhang Shu , Tan Yanhong , Hong Weiyao , Cheng Bo , Chen Qingxin , Zhu Yuntao , Feng Lianshun . Progress in the Synthesis of Sialic Acid Derivatives[J]. Chinese Journal of Organic Chemistry, 2014 , 34(3) : 461 -474 . DOI: 10.6023/cjoc201309032

References

[1] Somers, W. S.; Tang, J. Cell 2000, 103, 467.

[2] Rosen, S. D. Annu. Rev. Immunol. 2004, 22, 129.

[3] Lopez, P. H. H.; Schnaar, R. L. Curr. Opin Struct. Biol. 2009, 19, 549.

[4] Dube, D. H.; Bertozzi, C. R. Nat. Rev. Drug Discovery 2005, 4, 477.

[5] Chen, X.; Varki, A. ACS Chem. Biol. 2010, 5, 163.

[6] Bertozzi, C. R.; Kiessling L. L. Science 2001, 291, 2357.

[7] Cheng, C.; Gao, C.-F. Lab. Med. 2013, 4, 333 (in Chinese).

(程铖, 高春芳, 检验医学, 2013, 4, 333.)

[8] Li, L.-S.; Liu, K.-G.; Yao, Z.-J.; Wu, Y.-L. Chin. J. Org. Chem. 2002, 22, 718 (in Chinese).

(李连生, 刘克刚, 姚祝军, 吴毓林, 有机化学, 2002, 22, 718.)

[9] Luchansky, S. J.; Goon, S.; Bertozzi, C. R. ChemBioChem 2004, 5(3), 371.

[10] Oetke, C.; Brossmer, R.; Mantey, L. R.; Hinderlich, S.; Isecke, R.; Reutter, W.; Keppler, O. T.; Pawlita, M. J. Biol. Chem. 2002, 277(8), 6688.

[11] Oetke, C.; Hinderlich, S.; Brossmer, R.; Reutter, W.; Pawlita, M.; Keppler, O. T. Eur. J. Biochem. 2001, 268(16), 4553.

[12] Möller, H.; Böhrsch, V.; Bentrop, J.; Bender, J.; Hinderlich, S.; Hackenberger, C. P. R. Angew. Chem., Int. Ed. 2012, 51, 5986.

[13] Han, S.; Collins, B. E.; Bengtson, P.; Paulson, J. C. Nat. Chem. Biol. 2005, 1(2), 93.

[14] Tanaka, Y.; Kohler, J. J. J. Am. Chem. Soc. 2008, 130, 3278.

[15] Uchiyama, T.; Vassilev, V. P.; Kajimoto, T.; Wo, C.-H. J. Am. Chem. Soc. 1995, 117, 5395.

[16] Chan, T.-H.; Xin, Y.-C. Chem. Commun. 1996, 1(8), 905.

[17] Chan T.-H., Xin, Y.-C. J. Org. Chem. 1997, 62, 3500.

[18] Gao, J.; Martichonok, V.; Whitesides, G. M. J. Org. Chem. 1996, 61, 9538.

[19] Hagedorn, H.; Merten, H.; Brossmer, R. Carbohydr. Res. 1992, 236, 89.

[20] Zhang, D.-Y.; Ye, D.-J.; Wang, J.-F.; Shi, J.-M.; Jiang, H.-L.; Liu, H. J. Org. Chem. 2010, 75, 3552.

[21] Pan, Y.; Ayani, T.; Nadas, J.; Wen, S.; Guo, Z. Carbohydr. Res. 2004, 339(12), 2091.

[22] Ikeuchi, Y.; Sumiya, M.; Kawamoto, T.; Akimoto, N.; Mikata, Y.; Kishigami, M.; Yano, S.; Sasakic, T.; Yoneda, F. Bioorg. Med. Chem. 2000, 8, 2027.

[23] Knoll, T. L.; Bennet, A. J. J. Phys. Org. Chem. 2004, 17, 478.

[24] Chou, D. T. H.; Watson, J. N.; Scholte, A. A.; Borgford, T. J.; Bennet, A. J. J. Am. Chem. Soc. 2000, 122, 8357.

[25] Zamora, C. Y.; Alarcao, M.; Kumar, K. Bioorg. Med. Chem. Lett. 2013, 23, 3406.

[26] Sakamoto, J. I.; Koyama, T.; Miyamoto, D.; Yingsakmongkon, S.; Hidari, K. I. P. J.; Jampangern, W.; Suzuki, T.; Suzuki, Y.; Esumi, Y.; Nakamura, T.; Hatano, K.; Terunuma, D.; Matsuoka, K. Med. Chem. 2009, 17, 5451.

[27] Hinou, H.; Kurogochi, M.; Shimizu, H.; Nishimura, S. Biochem. 2005, 44, 11669.

[28] Matsuoka, K.; Onaga, T.; Mori, T.; Sakamoto, J. I.; Koyama, T.; Sakairi, N.; Hatano, K.; Terunuma, D. Tetrahedron Lett. 2004, 45, 9383.

[29] Abo, S.; Ciccotosto, S.; Alafaci, A.; Itzstein, M. Carbohydr. Res. 1999, 322, 201.

[30] Matsuoka, K.; Takita, C.; Koyama, T.; Miyamoto, D.; Yingsakmongkon, S.; Hidari K. I. P. J.; Jampangern, W.; Suzuki, T.; Suzuki, Y.; Hatano, K.; Terunuma, D. Bioorg. Med. Chem. Lett. 2007, 17, 3826.

[31] Morais, G. R.; Oliveira, I. F.; Humphrey, A. J.; Falconer, R. A. Carbohydr. Res. 2010, 345, 160.

[32] Sakamoto, J. I.; Koyama, T.; Miyamoto, D.; Yingsakmongkon, S.; Hidari, K. I. P. J.; Jampangern, W.; Suzuki, T.; Suzuki, Y.; Esumi, Y.; Hatano, K.; Terunuma, D.; Matsuoka, K. Bioorg. Med. Chem. Lett. 2007, 17, 717.

[33] Klefel, M. J.; Ltzstein, M. Tetrahedron Lett. 1996, 37(40), 7307.

[34] Noel, A.; Delpech, B.; Crich, D. Org. Lett. 2012, 14(5), 1342.

[35] Gantt, R.; Millner, S.; Binkley, S. B. Biochemistry 1964, 3(12), 1952.

[36] Hagiwara, T.; Kijima-Suda, I.; Ido, T.; Ohrui, H.; Tomita, K. Carbohydr. Res. 1994, 263(1), 167.

[37] Burkart, M. D.; Vincent, S. P.; Düffels, A.; Murray, B. W.; Ley, S. V.; Wong, C.-H. Bioorg. Med. Chem. 2000, 8(8), 1937.

[38] Sun, X.-L.; Kanie, Y.; Guo, C.; Kanie, O.; Suzuki, Y.; Wong, C.-H. Eur. J. Org. Chem. 2000, 14, 2643.

[39] Guo, C.-T.; Sun, X.-L.; Kanie, O.; Shortridge, K. F.; Suzuki, T.; Miyamoto, D.; Hidari, K. I.; Wong, C.-H.; Suzuki, Y. Glycobiol 2002, 12(3), 183.

[40] Watts, A. G.; Damager, I.; Amaya, M. L.; Buschiazzo, A.; Alzari, P.; Frasch, A. C.; Withers, S. G. J. Am. Chem. Soc. 2003, 125(25), 7532.

[41] Buchini, S.; Buschiazzo, A.; Withers, S. G. Angew. Chem., Int. Ed. 2008, 47(14), 2700.

[42] Chokhawala, H. A.; Cao, H.; Yu, H.; Chen, X. J. Am. Chem. Soc. 2007, 129, 10630.

[43] Tsai, C.-S.; Yen, H.-Y.; Lin, M.; Tsai, T.; Wang, S.-Y.; Huang, W.; Hsu, T.-L.; Cheng, Y.-S.-E.; Fang, J.-M.; Wong, C.-H. Proc. Natl. Acad. Sci. U. S. A. 2013, 110(7), 2466.

[44] Burkart, M.; Zhang, Z.; Hung, S.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 11743.

[45] Rillahan, C. D.; Antonopoulos, A.; Lefort, C. T.; Sonon, R.; Azadi, P.; Ley, K.; Dell, A.; Haslam, S. M.; Paulson, J. C. Nat. Chem. Biol. 2012, 8(7), 661.

[46] Hader, S.; Watts, A. G. Carbohydr. Res. 2013, 374, 23.

[47] Rudrawar, S.; Dyason, J. C.; Maggioni, A.; Thomson, R. J.; Itzstein, M. Bioorg. Med. Chem. 2013, 21(16), 4820.

[48] Rudrawar, S.; Pascolutti, M.; Bhatt, B.; Thomson, R.; Itzstein, M. Tetrahedron Lett. 2013, 54, 1198.

[49] Zhang, J.; Xu, W.-F. Chin. J. Pharm. 2005, 36(10), 643 (in Chinese).

(张杰, 徐文方, 中国医药工业杂志, 2005, 36(10), 643.)

[50] Zhu, X.-B.; Wang, M.; Wang, S.-Z.; Yao, Z.-J. Tetrahedron 2012, 68, 2041.

[51] Nishino, R.; Ikeda, K.; Hayakawa, T.; Takahashi, T.; Suzuki, T.; Sato, M. Bioorg. Med. Chem. 2011, 19, 2418.

[52] Ikeda, K.; Sato, K.; Kitani, S.; Suzuki, T.; Maki, N.; Suzuki, Y.; Sato, M. Bioorg. Med. Chem. 2006, 14, 7893.

[53] Ikeda, K.; Sato, K.; Nishino, R.; Aoyama, S.; Suzuki, T.; Sato, M. Bioorg. Med. Chem. 2008, 16, 6783.

[54] Ye, D. J.; Li, J.; Zhang, J.; Liu, H.; Jiang, H. L. Tetrahedron Lett. 2007, 48, 4023.

[55] Ye, D.; Deng, G.; Liu, W.; Zhou, Y.; Feng, E.; Jiang, H.; Liu, H. Tetrahedron Lett. 2008, 64, 6544.

[56] Ye, D.; Shin, W. J.; Li, N.; Tang, W.; Feng, E.; Li, J.; He, P. L.; Zuo, J. P.; Kim, H.; Nam, K. Y.; Zhu, W.; Seong, B. L.; No, K. T.; Jiang, H.; Liu, H. Eur. J. Med. Chem. 2012, 54, 764.

[57] Liu, K.-G.; Yan, S.; Wu, Y.-L., Yao, Z.-J. J. Org. Chem. 2002, 67, 6758.

[58] Liu, K.-G.; Zhou, H.-B.; Wu, Y.-L.; Yao, Z.-J. J. Org. Chem. 2003, 68, 9528.

[59] Gao, Z.-X.; Wang, M.; Wang, S.-Z.; Yao, Z.-J. Org. Lett. 2009, 11, 3678.

[60] Comb, D. G.; Roseman, S. J. Am. Chem. Soc. 1958, 80, 497.

[61] Kok, G. B.; Campbell, M.; Mackey, B. L.; Itzstein, M. Carbohydr. Res. 2001, 332, 133.

[62] Lin, L.; Tian, X.; Hong, S.; Dai, P.; You, Q.; Wang, R.; Feng, L.; Xie, C.; Tian, Z.; Chen, X. Angew. Chem., Int. Ed. 2013, 52(28), 7266.

[63] Chang, P.; Chen, X.; Smyrniotis, C.; Xenakis, A.; Hu, T.; Bertozzi, C. R.; Wu, P. Angew. Chem., Int. Ed. 2009, 48, 4030.

[64] Bond, M. R.; Zhang, H.; Kim, J.; Yu, S. H.; Yang, F.; Patrie, S. M.; Kohler J. J. Bioconjugate Chem. 2011, 22(9), 1811.

[65] Kragl, U.; Gygax, D.; Ghisalba, O.; Wandrey, C. Angew. Chem., Int. Ed. 1991, 30, 827.

[66] Wu, W. Y.; Jin, B.; Kong, D. C. M.; Itzstein, M. Carbohydr. Res. 1997, 300, 171.

[67] Brossmer, R.; Acher, F.; Debacker, C.; Bertrand, H. O.; Ruivo, R.; Sagné, C.; Pietrancosta, N.; Horst, C. A. J. Biol. Chem. 2012, 287(14), 11489.

[68] Cao, H.; Muthana, S.; Li, Y.; Cheng, J.; Chen, X. Bioorg. Med. Chem. Lett. 2009, 19, 5869.

[69] Suzuki, K.; Sakamoto, J. I.; Koyama, T.; Yingsakmongkon, S.; Suzuki, Y.; Hatano, K.; Terunuma, D.; Matsuoka, K. Bioorg. Med. Chem. Lett. 2009, 19, 5105.

[70] Suzuki, K.; Koyama, T.; Yingsakmongkon, S.; Suzuki, Y.; Hatano, K.; Matsuoka, K. Bioorg. Med. Chem. 2012, 20, 446.

[71] Johansson, S.; Nilsson, E.; Qian, W.; Guilligay, D.; Crepin, T.; Cusack, S.; Arnberg, N.; Elofsson, M. J. Med. Chem. 2009, 52, 3666.

[72] Ogura, H.; Furuhata, K. Carbohydr. Res. 1986, 158, 37.

[73] Allevi, P.; Anastasia, M.; Costa, M. L.; Rota, P. Tetrahedron: Asymmetry 2011, 22, 338.

[74] Honda, T.; Masuda, T.; Yoshida, S.; Arai, M.; Kobayashi, Y.; Yamashita, M. Bioorg. Med. Chem. Lett. 2012, 12, 1921.

[75] Thomson, R.; Itzstein, M. Carbohydr. Res. 1995, 274, 29.

[76] Kong, D. C. M.; Itzstein, M. Tetrahedron Lett. 1995, 36(6), 957.

[77] Wu, J.-R.; Zhan, X.-B.; Zheng, Z.-Y.; Jia, W. Chin. J. Bioprocess Eng. 2007, 5(1), 20 (in Chinese).

(吴剑荣, 詹晓北, 郑志永, 贾薇, 生物加工过程, 2007, 5(1), 20.)

[78] Rockle, I.; Seidenfaden, R.; Weinhold, B.; Muhlenhoff, M.; Gerardy-Schahn, R.; Hildebrandt, H. Dev. Neurobiol. 2008, 68, 1170.

[79] Rutishauser, U.; Acheson, A.; Hall, A. K.; Mann, D. M.; Sunshine, J. Science 1988, 240, 53.

[80] Cipolla, L.; Peri, F.; Airoldi, C. Curr. Med. Chem. Anti-Cancer Agents 2008, 8, 92.

[81] Jennings, H. J.; Roy, R.; Michon, F. J. Immunol. 1985, 134, 2651.

[82] Morley, T. J.; Withers, S. G. J. Am. Chem. Soc. 2010, 132, 9430.

[83] Weïwer, M.; Chen, C. C.; Kemp, M. M. Eur. J. Org. Chem. 2009, 16, 2611.

[84] Shelke, S. V.; Gao. G. P.; Mesch, S.; Gäthje, H.; Kelm, S.; Ernst, O. S. B. Bioorg. Med. Chem. 2007, 15, 4951.

[85] Yu, H.; Cao, H.; Tiwari, V. K.; Li, Y.; Chen, X. Bioorg. Med. Chem. Lett. 2011, 21, 5037.

[86] Schauer, R. Curr. Opin. Struct. Biol. 2009, 19, 507.

[87] Varki, A. Trends Mol. Med. 2008, 14, 351.

[88] Hedlund, M.; Padler-Karavani, V.; Varki, N. M.; Varki, A. Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 18936.

[89] Inoue, S.; Sato, C.; Kitajima, K. Glycobiol 2010, 20, 752.

[90] Kiefel, M. J.; Chopra, P.; Madge, P. D.; Szyczew, A.; Thomson, R. J.; Grice, I. D.; Itzstein, M. Tetrahedron Lett. 2011, 52, 98.

[91] Powell, L. D.; Sgroi, D.; Sjoberg, E. R.; Stamenkovic, I.; Varki, A. J. Biol. Chem. 1993, 268(10), 7019.

[92] Law, C. L.; Aruffo, A.; Chandran, K. A.; Doty, R. T.; Clark, E. A. J. Immunol. 1995, 155(7), 3368.

[93] Greer, S. F.; Justement, L. B. J. Immunol. 1999, 162(9), 5278.

[94] Fujimoto, M.; Bradney, A. P.; Poe, J. C.; Steeber, D. A.; Tedder, T. F. Immunity 1999, 11(2), 191.

[95] Collins, B. E.; Blixt, O.; DeSieno, A. R.; Bovin, N.; Marth, J. D.; Paulson, J. C. Proc. Natl. Acad. Sci. U. S. A. 2004, 101(16), 6104.

[96] Yadav, R.; Kikkeri, R. Chem. Commun. 2012, 48, 7265.

[97] Patterson, D. M.; Nazarova, L. A.; Xie, B.; Kamber, D. N.; Prescher, J. A. J. Am. Chem. Soc. 2012, 134, 18638.

[98] Abdu-Allah, H. H. M.; Watanabe, K.; Completo, G. C.; Sadagopan, M.; Hayashizaki, K.; Takaku, C.; Tamanaka, T.; Takematsu, H.; Kozutsumi, Y.; Paulson, J. C.; Tsubata, T.; Ando, H.; Ishida, H.; Kiso, M. Bioorg. Med. Chem. 2011, 19, 1966.

[99] Yu, H.; Karpel, R.; Chen, X. Bioorg. Med. Chem. 2004, 12, 6427.

[100] Martin, R.; Witte, K. L.; Wong, C.-H. Bioorg. Med. Chem. 1998, 6, 1283.

[101] Liu J. L. C.; Shen, C. J.; Ichikawa, Y.; Rutan, J. F.; Zapata, C.; Vann, W. F.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 3901.

[102] Feng, L.-S.; Hong, S.-L.; Rong, J.; You, Q.-C.; Dai, P.; Huang, R.-B.; Tan, Y.-H.; Hong, W.-Y.; Xie, C.; Zhao, J.; Chen, X. J. Am. Chem. Soc. 2013, 135(25), 9244.

[103] Seeberger, P. H.; Haase, W. C. Chem. Rev. 2000, 100(12), 4349.

[104] Giepmans, B. N.; Adams, S. R.; Ellisman, M. H.; Tsien, R. Y. Science 2006, 312(5771), 217.

[105] Lecuyer, E.; Yoshida, H.; Parthasarathy, N.; Alm, C.; Babak, T.; Cerovina, T.; Hughes, T. R.; Tomancak, P.; Krause, H. M. Cell 2007, 131(1), 174.

[106] Dube, D. H.; Bertozzi, C. R. Curr. Opin. Chem. Biol. 2003, 7, 616.

[107] Laughlin, S. T.; Baskin, J. M.; Amacher, S. L.; Bertozzi, C. R. Science 2008, 320(5876), 664.

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