SIOC English
有机化学
高级检索

有机化学 >

2012 , Vol. 32 >Issue 08: 1388 - 1400

DOI: https://doi.org/10.6023/cjoc1112081

综述与进展

肝素类寡糖合成研究进展

  • 尹晓娟 ,
  • 闫俊 ,
  • 姬胜利 ,
  • 王凤山 ,
  • 曹鸿志
展开
  • a 山东大学国家糖工程技术研究中心 济南 250012;
    b 山东大学药学院 济南 250012

收稿日期: 2011-12-08

  修回日期: 2012-02-15

  网络出版日期: 2012-03-09

基金资助

国家自然科学基金(Nos. 20902087, 21172135)和国家重点基础研究发展规划(973计划, No. 2012CB822102)资助项目.

收起

Recent Advances in the Synthesis of Heparan Sulfate Oligosaccharides

  • Yin Xiaojuan ,
  • Yan Jun ,
  • Ji Shengli ,
  • Wang Fengshan ,
  • Cao Hongzhi
Expand
  • a National Glycoengineering Research Center, Shandong University, Jinan 250012;
    b School of Pharmaceutical Science, Shandong University, Jinan 250012

Received date: 2011-12-08

  Revised date: 2012-02-15

  Online published: 2012-03-09

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 20902087, 21172135) and the National Basic Research Program of China (973 program, No. 2012CB822102).

Fold

摘要

肝素(heparin, HP)和硫酸乙酰肝素(heparan sulfate, HS)是糖胺聚糖(glycosaminoglycans, GAGs)家族中的一类线性硫酸化多糖, 其结构复杂、生物活性多样. 为了深入研究其结构序列与不同生物活性之间的关系, 近年来针对肝素类寡糖的合成与功能研究成为糖化学和糖生物学研究的一个热点领域, 涌现出一些新的合成方法与合成策略. 选取了2001年以来国际上一些在肝素类寡糖的化学合成和酶法合成方面的代表性工作予以综述.

关键词： 肝素; 硫酸乙酰肝素; 化学糖苷化; 糖基转移酶

本文引用格式

尹晓娟 , 闫俊 , 姬胜利 , 王凤山 , 曹鸿志 . 肝素类寡糖合成研究进展[J]. 有机化学, 2012 , 32(08) : 1388 -1400 . DOI: 10.6023/cjoc1112081

Abstract

Heparin (HP) and heparan sulfate (HS), a member of the glycosaminoglycan (GAG) family, are structurally related linear polyanionic polysaccharides. These complex sulfated polysaccharides can interact with hundreds of proteins and play essential roles in mediating or modulating a variety of physiological and pathological processes. Accumulated evidence has shown that the biological functions of HP and HS can be critically dependent upon their precise structure sequences. To decipher the sequence code of HS and HP, many research groups have focus on the development of novel strategies and synthetic methods for the assembling of heparin oligosaccharides during the last decade. The key developments since 2001 in the chemical or chemoenzymatic synthesis of heparin oligosaccharides are covered in this review.

Key words： heparin; heparan sulfate; chemical glycosylation; glycotransferase

参考文献

[1] Casu, B.; Lindahl, U. Adv. Carbohydr. Chem. Biochem. 2001, 57, 159.

[2] Capila, I.; Linhardt, R. J. Angew. Chem., Int. Ed. 2002, 41, 391.

[3] Raman, R.; Sasisekharan, V.; Sasisekharan, R. Chem. Biol. 2005, 12, 267.

[4] Sasisekharan, R.; Raman, R.; Prabhakar, V. Ann. Rev. Biomed. Eng. 2006, 8, 181.

[5] Petitou, M.; Duchaussoy, P.; Lederman, I.; Choay, J.; Sinay, P.; Jacquinet, J. C.; Torri, G. Carbohydr. Res. 1986, 147, 221.

[6] Petitou, M.; Duchaussoy, P.; Lederman, I.; Choay, J.; Jacquinet, J. C.; Sinay, P.; Torri, G. Carbohydr. Res. 1987, 167, 67.

[7] Petitou, M.; van Boeckel, C. A. A. Angew. Chem., Int. Ed. 2004, 43, 3118.

[8] Kovensky, J. Curr. Med. Chem. 2009, 16, 2338.

[9] Gandhi, N. S.; Mancera, R. L. Drug Discovery Today 2010, 15, 1058.

[10] Poletti, L.; Lay, L. Eur. J. Org. Chem. 2003, 2999.

[11] Karst, N. A.; Linhardt, R. J. Curr. Med. Chem. 2003, 10, 1993.

[12] Whitelock, J. M.; Iozzo, R. V. Chem. Rev. 2005, 105, 2745.

[13] Orgueira, H. A.; Bartolozzi, A.; Schell, P.; Seeberger, P. H. Angew. Chem., Int. Ed. 2002, 41, 2128.

[14] Orgueira, H. A.; Bartolozzi, A.; Schell, P.; Litjens, R.; Palmacci, E. R.; Seeberger, P. H. Chem. Eur. J. 2003, 9, 140.

[15] Lohman, G. J. S.; Seeberger, P. H. J. Org. Chem. 2004, 69, 4081.

[16] Adibekian, A.; Bindschadler, P.; Timmer, M. S. M.; Noti, C.; Schutzenmeister, N.; Seeberger, P. H. Chem. Eur. J. 2007, 13, 4510.

[17] Prabhu, A.; Venot, A.; Boons, G. J. Org. Lett. 2003, 5, 4975.

[18] Arungundram, S.; Al-Mafraji, K.; Asong, J.; Leach, F. E.; Amster, I. J.; Venot, A.; Turnbull, J. E.; Boons, G. J. J. Am. Chem. Soc. 2009, 131, 17394.

[19] Cao, H. Z.; Yu, B. Tetrahedron Lett. 2005, 46, 4337.

[20] Zhou, Y.; Lin, F.; Chen, J.; Yu, B. Carbohydr. Res. 2006, 341, 1619.

[21] Chen, J.; Zhou, Y.; Chen, C.; Xu, W.; Yu, B. Carbohydr. Res. 2008, 343, 2853.

[22] Chen, J. F.; Yu, B. Tetrahedron Lett. 2008, 49, 1682.

[23] Chen, C.; Yu, B. Bioorg. Med. Chem. Lett. 2009, 19, 3875.

[24] Hung, S. C.; Thopate, S. R.; Chi, F. C.; Chang, S. W.; Lee, J. C.; Wang, C. C.; Wen, Y. S. J. Am. Chem. Soc. 2001, 123, 3153.

[25] Lee, J. C.; Lu, X. A.; Kulkarni, S. S.; Wen, Y. S.; Hung, S. C. J. Am. Chem. Soc. 2004, 126, 476.

[26] Lu, N.-D. L.; Shie, C.-R.; Kulkarni, S. S.; Pan, G.-R.; Lu, X.-A.; Hung, S.-C. Org. Lett. 2006, 8, 5995.

[27] 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.

[28] Wang, C.-C.; Lee, J.-C.; Luo, S.-Y.; Kulkarni, S. S.; Huang, Y.-W.; Lee, C.-C.; Chang, K.-L.; Hung, S.-C. Nature 2007, 446, 896.

[29] Codee, J. D. C.; Stubba, B.; Schiattarella, M.; Overkleeft, H. S.; van Boeckel, C. A. A.; van Boom, J. H.; van der Marel, G. A. J. Am. Chem. Soc. 2005, 127, 3767.

[30] Zhang, Z. Y.; Ollmann, I. R.; Ye, X. S.; Wischnat, R.; Baasov, T.; Wong, C. H. J. Am. Chem. Soc. 1999, 121, 734.

[31] Polat, T.; Wong, C. H. J. Am. Chem. Soc. 2007, 129, 12795.

[32] Yu, H. N.; Furukawa, J.; Ikeda, T.; Wong, C. H. Org. Lett. 2004, 6, 723.

[33] Huang, X. F.; Huang, L. J.; Wang, H. S.; Ye, X. S. Angew. Chem., Int. Ed. 2004, 43, 5221.

[34] Wang, Z.; Xu, Y. M.; Yang, B.; Tiruchinapally, G.; Sun, B.; Liu, R. P.; Dulaney, S.; Liu, J. A.; Huang, X. F. Chem. Eur. J. 2010, 16, 8365.

[35] Al-Horani, R. A.; Desai, U. R. Tetrahedron 2010, 66, 2907.

[36] Miller, S. C. J. Org. Chem. 2010, 75, 4632.

[37] Ingram, L. J.; Taylor, S. D. Angew. Chem., Int. Ed. 2006, 45, 3503.

[38] Desoky, A. Y.; Taylor, S. D. J. Org. Chem. 2009, 74, 9406.

[39] Tiruchinapally, G.; Yin, Z.; El-Dakdouki, M.; Wang, Z.; Huang, X. Chem. Eur. J. 2011, 17, 10106.

[40] Chen, J. H.; Avci, F. Y.; Munoz, E. M.; McDowell, L. M.; Chen, M.; Pedersen, L. C.; Zhang, L. J.; Linhardt, R. J.; Liu, J. J. Biol. Chem. 2005, 280, 42817.

[41] Martin, J. G.; Gupta, M.; Xu, Y.; Akella, S.; Liu, J.; Dordick, J. S.; Linhardt, R. J. J. Am. Chem. Soc. 2009, 131, 11041.

[42] Liu, R. P.; Xu, Y. M.; Chen, M. A.; Weiwer, M.; Zhou, X. X.; Bridges, A. S.; DeAngelis, P. L.; Zhang, Q. S.; Linhardt, R. J.; Liu, J. A. J. Biol. Chem. 2010, 285, 34240.

[43] Xu, Y.; Masuko, S.; Takieddin, M.; Xu, H.; Liu, R.; Jing, J.; Mousa, S. A.; Linhardt, R. J.; Liu, J. Science 2011, 334, 498.

[44] Paulsen, H. Angew. Chem., Int. Ed. 1982, 21, 155.
Options
文章导航

/

〈 〉