Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (3): 461-474.DOI: 10.6023/cjoc201309032 Previous Articles Next Articles
Articles
王汝一a, 张姝b, 谭艳红a, 洪伟耀a, 成波a, 陈庆鑫a, 朱蕴韬a, 冯连顺a,c
收稿日期:2013-09-23
修回日期:2013-11-10
发布日期:2013-12-06
通讯作者:
冯连顺
E-mail:ochemistry@163.com
基金资助:深圳市战略新兴产业发展专项资金（No. JCYJ20130329174913512）；中国博士后科学基金面上（No. 2013M540013）资助项目.
Wang Ruyia, Zhang Shub, Tan Yanhonga, Hong Weiyaoa, Cheng Boa, Chen Qingxina, Zhu Yuntaoa, Feng Lianshuna,c
Received:2013-09-23
Revised:2013-11-10
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).
Share
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]. Chin. J. Org. Chem., 2014, 34(3): 461-474.
| [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. |
| [1] | Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656. |
| [2] | Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604. |
| [3] | Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437. |
| [4] | Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408. |
| [5] | Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308. |
| [6] | Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194. |
| [7] | Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147. |
| [8] | Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281. |
| [9] | Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258. |
| [10] | Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110. |
| [11] | Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223. |
| [12] | Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241. |
| [13] | Xiaoying Jia, Jiaxia Pu, Lirong Han, Qinghan Li. Research Progress in the Synthesis of Benzo[d]pentamembered Heterocyclic Thioethers Containing Two Heteroatoms [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 18-40. |
| [14] | Ruixia Cao, Yuping Jia. Synthesis and Biological Activity of Novel Pyrrolo[2,3-d]pyrimidine Derivatives Containing Coumarin [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3304-3311. |
| [15] | Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077. |
| Viewed | ||||||
|
Full text |
|
|||||
|
Abstract |
|
|||||
