中文   |   English   |   Email Alert

水相中糖识别人工受体

熊雨婷, 李闵闵, 熊鹏, 杨梦, 卿光焱*, 孙涛垒*

化学进展 ›› 2014, Vol. 26 ›› Issue (01) :48-60

PDF (4147KB)
化学进展 ›› 2014, Vol. 26 ›› Issue (01) :48-60 DOI: 10.7536/PC130631
综述与评论
扫码查看或转发全文

水相中糖识别人工受体

    熊雨婷, 李闵闵, 熊鹏, 杨梦, 卿光焱*, 孙涛垒*
作者信息 +

Artificial Carbohydrate Receptors in Aqueous Media

  • Xiong Yuting, Li Minmin, Xiong Peng, Yang Meng, Qing Guangyan*, Sun Taolei*
Author information +
文章历史 +

摘要

自然界中,糖类不仅作为生命体系的能量物质和结构物质,而且还作为信息分子在生命过程的细胞识别和调控中扮演着重要的角色,因此对糖识别的研究将极大地有助于糖类参与生理和病理过程的研究。生命体系中糖识别过程一方面基于受体的极性基团与糖羟基的氢键作用,另一方面依靠受体结构中的含芳环非极性基团与糖CH基相互作用,所以在极性溶液水中通过非共价键相互作用实现糖识别过程是当今化学界一个十分吸引人且又极具挑战性的研究课题。人工合成糖识别受体为研究自然界中糖识别过程的基本机制提供了一种有参考价值的模型系统,同时为仿生应用提供了有力的技术支持。本文从超分子化学、多分枝型、合成凝集素类和聚合物界面4种体系论述了近年来非硼酸类人工糖识别受体在水相中识别糖的研究进展及其潜在应用,并且对合成凝集素和界面糖识别体系做了特殊点评,最后对仿生人工合成受体在水相中对糖识别的未来的发展方向做了展望。

Abstract

In nature, carbohydrates are not only known as energy substances and structural materials of life, but also famous as signaling molecules that play critical roles in cell recognition and regulation processes. Therefore, the investigation and simulation of carbohydrates recognition process will greatly contribute to the research of some pathological process involved with carbohydrate, which has attracted great interests in the development of artificial receptors for carbohydrates. Inspiring from protein-carbohydrate interactions in biological system, most of recognition procedures are based on two binding modes, one is hydrogen bonding interaction between hydroxyl groups of carbohydrates and polar residues of the receptors, the other is σ-π stacking or even sandwich inclusion involving CH moieties of carbohydrates and aromatic segments of receptors. Although significant progresses in carbohydrates sensing in organic solvents have been achieved in the past few decades, the binding of carbohydrates and their derivatives with high sensitivity and specific selectivity in aqueous solution still remains as one of the most interesting but challenging topics in current chemistry. Therefore, the investigation of these artificial receptors not only provides a series of valuable model systems mimicking natural products for carbohydrate recognition, but also promotes many biomimetic applications. In this work, the recent progresses on artificial receptors for carbohydrates in aqueous media are summarized from four aspects: supramolecular chemistry system, multi-branch architecture system, synthetic lectins and polymeric interface system. Among which we specifically highlight the synthetic lections and a novel carbohydrate recognition strategy based on polymeric interface materials. Finally, the research prospects are proposed briefly.

Contents
1 Introduction
2 Supramolecular chemistry systems
2.1 Cyclodextrin
2.2 Curdlan
2.3 Calixarene
2.4 Porphyrin
3 Multi-branch architecture systems
3.1 Dicarboxylate
3.2 Cyclopentane
3.3 Guanidinium and analogues
4 Synthetic lectins
4.1 Macrocyclic synthetic lectins
4.2 Polymer-based synthetic lectins
4.3 Oligo-peptide-based synthetic lectins
5 Polymeric interface systems
6 Conclusion and outlook

关键词

糖识别 / 人工受体 / 水相 / 非共价键相互作用 / 仿生

Key words

carbohydrate recognition / artificial receptors / aqueous media / noncovalent interaction / biomimetic

引用本文

引用格式 ▾
熊雨婷, 李闵闵, 熊鹏, 杨梦, 卿光焱, 孙涛垒. 水相中糖识别人工受体[J]. 化学进展, 2014, 26(01): 48-60 DOI:10.7536/PC130631
Xiong Yuting, Li Minmin, Xiong Peng, Yang Meng, Qing Guangyan, Sun Taolei. Artificial Carbohydrate Receptors in Aqueous Media[J]. Progress in Chemistry, 2014, 26(01): 48-60 DOI:10.7536/PC130631

登录浏览全文

4963

注册一个新账户 忘记密码

参考文献

[1] Bertozzi C R, Kiessling L L. Science, 2001, 291: 2357.
[2] James T D, Sandanayake K R A S, Shinkai S. Nature, 1995, 374: 345.
[3] Pal A, Bérubé M, Hall D G. Angew. Chem. Int. Ed., 2010, 49: 1492.
[4] Striegler S. Curr. Org. Chem., 2003, 7: 81.
[5] Davis A P, Warehem R S. Angew. Chem. Int. Ed., 1999, 38: 2978.
[6] Dai C F, Sagwal A, Cheng Y F, Peng H J, Chen W X, Wang B H. Pure Appl. Chem., 2012, 84: 2479.
[7] Mazik M. Chem. Soc. Rev., 2009, 38: 935.
[8] Mazik M. RSC Adv., 2012, 2: 2630.
[9] Walker D B, Joshi G, Davis A P. Cell. Mol. Life Sci., 2009, 66: 3177.
[10] Zeng X, Andrade C A S, Oliveira M D L, Sun X L. Anal. Bioanal. Chem., 2012, 402: 3161.
[11] Fujimoto Y K, Green D F. J. Am. Chem. Soc., 2012, 134: 19639.
[12] 黄毅(Huang Y), 黄金花(Huang J H), 谢青季(Xie Q J), 姚守拙(Yao S Z). 化学进展(Progress in Chemistry), 2008, 20(6): 942.
[13] Mazik M, Hartmann A, Jones P G. Chem. Eur. J., 2009, 15: 9147.
[14] Edwards N Y, Sager T W, McDevitt J T, Anslyn E V. J. Am. Chem. Soc., 2007, 129: 13575.
[15] Rusin O, Lang K, Král V. Chem. Eur. J., 2002, 8: 655.
[16] Ishi-i T, Mateos-Timoneda M A, Timmerman P, Crego-Calama M, Reinhoudt D N, Shinkai S. Angew. Chem. Int. Ed., 2003, 42: 2300.
[17] Lehn J M. Science, 1993, 260: 1762.
[18] Oshovsky G V, Reinhoudt D N, Verboom W. Angew. Chem. Int. Ed., 2007, 46: 2366.
[19] 孔蕊(Kong R), 施冬健(Shi D J), 刘蓉瑾(Liu R J), 陈明清(Chen M Q). 高分子通报 (Polymer Bulletin), 2012, (12): 36.
[20] Aoyama Y, Nagai Y, Otsuki J, Kobayashi K, Toi H. Angew. Chem. Int. Ed., 1992, 31: 745.
[21] Hirsch W, Muller T, Pizer R, Ricatto P J. Can. J. Chem., 1995, 73: 12.
[22] Hacket F, Coteron J M, Schneider H J, Kazachenko V P. Can. J. Chem., 1997, 75: 52.
[23] Easton C J, Lincoln S F. Chem. Soc. Rev., 1996, 25: 163.
[24] Danil de Namor A F, Blackett P M, Cabaleiro M C, Al Rawi J M A. J. Chem. Soc. Faraday Trans., 1994, 90: 845.
[25] Eliseev A V, Schneider H J. J. Am. Chem. Soc., 1994, 116: 6081.
[26] Sakurai K, Uezu K, Numata M, Hasegawa T, Li C, Kaneko K, Shinkai S. Chem. Commun., 2005, 4383.
[27] Numata M, Shinkai S. Adv. Polym. Sci., 2008, 220: 65.
[28] Fukuhara G, Inoue M. Chem. Commun., 2010, 46: 9128.
[29] Fukuhara J, Inoue Y. J. Am. Chem. Soc., 2011, 133: 768.
[30] 卿光焱(Qing G Y), 刘顺英(Liu S Y), 何永炳(He Y B). 化学进展 (Progress in Chemistry), 2008, 20(12): 1933.
[31] Aoyama Y, Tanaka Y, Toi H, Ogoshi H. J. Am. Chem. Soc., 1988, 110: 634.
[32] Kobayashi K, Asakawa Y, Kato Y, Aoyama Y. J. Am. Chem. Soc., 1992, 114: 10307.
[33] Yanagihara R, Aoyama Y. Tetrahedron Lett., 1994, 35: 9725.
[34] Nishio M, Umezawa Y, Hirota M, Takeuchi Y. Tetrahedron, 1995, 51: 8665.
[35] Poh B L, Tan C M. Tetrahedron, 1993, 49: 9581.
[36] Poh B L, Tan C M. Tetrahedron Lett., 1994, 35: 6387.
[37] 张春(Zhang C), 郑炎松(Zheng Y S), 梅付名(Mei F M), 李光兴(Li G X). 化学进展 (Progress in Chemistry), 2004, 16(6): 935.
[38] Rusin O, Král V. Tetrahedron Lett., 2001, 42: 4235.
[39] Král V, Rusin O, Charvatova J, Anzenbacher P, Fogl J. Tetrahedron Lett., 2000, 41: 10147.
[40] Charvatova J, Rusin O, Král V, Volka K, Matejka P. Sensor Actuat. B Chem., 2001, 76: 366.
[41] Král V, Rusin O, Schmidtchen F P. Org. Lett., 2001, 3: 873.
[42] Rusin O, Lang K, Král V. Chem. Eur. J., 2002, 8: 655.
[43] Mazik M, Cavga J. J. Org. Chem., 2006, 71: 2957.
[44] Hubbard R D, Horner S R, Miller B L. J. Am. Chem. Soc., 2001, 123: 5810.
[45] Blondeau P, Segura M, Pérez-Fernández R, Mendoza J. Chem. Soc. Rev., 2007, 36: 198.
[46] Mazik M, Cavga H. J. Org. Chem., 2007, 72: 831.
[47] Mazik M, Cavga H. Eur. J. Org. Chem., 2007, 3633.
[48] Schmuck C, Schwegmann M. J. Am. Chem. Soc., 2005, 127: 3373.
[49] Schmuck C, Schwegmann M. Org. Lett., 2005, 7: 3517.
[50] Kubik S. Angew. Chem. Int. Ed., 2009, 48: 1722.
[51] Arnaud J, Audfray A, Imberty A. Chem. Soc. Rev., 2013, 42: 4798.
[52] Davis A P, Wareham R S. Angew. Chem. Int. Ed., 1998, 37: 2270.
[53] Ryan T J, Lecollinet G, Velasco T, Davis A P. Proc. Natl. Acad. Sci. U. S. A., 2002, 99: 4863.
[54] Barwell N P, Davis A P. J. Org. Chem., 2011, 76: 6548.
[55] Joshi G, Davis A P. Org. Biomol. Chem., 2012, 10: 5760.
[56] Klein E, Crump M P, Davis A P. Angew. Chem. Int. Ed., 2005, 44: 298.
[57] Ferrand Y, Klein E, Barwell N P, Crump M P, Jimenez-Barbero J, Vicent C, Boons G J, Ingale S, Davis A P. Angew. Chem. Int. Ed., 2009, 48, 1775.
[58] Barwell N P, Crump M P, Davis A P. Angew. Chem. Int. Ed., 2009, 48: 7673.
[59] Ferrand Y, Crump M P, Davis A P. Science, 2007, 318: 619.
[60] Sookcharoenpinyo B, Klein E, Ferrand Y, Walker D B, Brotherhood P R, Ke C F, Crump M P, Davis A P. Angew. Chem. Int. Ed., 2012, 51: 4586.
[61] Ke C, Destecroix H, Crump M P, Davis A P. Nat. Chem., 2012, 4: 718.
[62] Hayley Birch. Sensor a Snug Fit for Glucose. (2012-08-06). http://www. rsc. org/chemistryworld/2012/08/sensor-snug-fit-glucose.
[63] Alexandre K B, Gray E S, Mufhandu H, McMahon J B, Chakauya E, O'Keefe B R, Chikwamba R, Morris L. Virology, 2012, 423: 175.
[64] Balzarini J. Antiviral Res., 2006, 71: 237.
[65] Jay J I, Lai B E, Myszka D G, Mahalingam A, Langheinrich K, Katz D F, Kiser P F. Mol. Pharmaceutics, 2010, 7: 116.
[66] Mahalingam A, Geonnotti A R, Balzarini J, Kiser P F. Mol. Pharm., 2011, 8: 2465.
[67] Bérubé M, Dowlut M, Hall D G. J. Org. Chem., 2008, 73: 6471.
[68] Lasky L A. Science, 1992, 258: 964.
[69] Otsuki J, Kobayashi K, Toi H, Aoyama Y. Tetrahedron Lett., 1993, 34: 1945.
[70] Sugimoto N, Mioshi D, Zou J. Chem. Commun., 2000, 2295.
[71] Reenberg T, Nyberg N, Duus J O, van Dongen J L J, Meldal M. Eur. J. Org. Chem., 2007, 5003.
[72] Lehn J M, Eliseev A V. Science, 2001, 291: 2331.
[73] 陈玉岩(Chen Y Y), 刘刚(Liu G). 化学进展 (Progress in Chemistry), 2007, 19(12): 1903.
[74] Rauschenberg M, Bomke S, Karst U, Ravoo B J. Angew. Chem. Int. Ed., 2010, 49: 7340.
[75] Arndt N X, Tiralongo J, Madge P D, von Itzstein M, Day C J. J. Cell. Biochem., 2011, 112: 2230.
[76] Ariga K, Kunitake T, Acc. Chem. Res., 1998, 31: 371.
[77] Sun T L, Qing G Y, Su B L, Jiang L. Chem. Soc. Rev., 2011, 40: 2909.
[78] Sun T L, Qing G Y. Adv. Mater., 2011, 23: H57.
[79] Zhang M X, Qing G Y, Sun T L. Chem. Soc. Rev., 2012, 41: 1972.
[80] Qing G Y, Wang X, Fuchs H, Sun T L. J. Am. Chem. Soc., 2009, 131: 8370.
[81] Qing G Y, Wang X, Jiang L, Fuchs H, Sun T L. Soft Matter, 2009, 5: 2759.
[82] Qing G Y, Sun T L. NPG Asia Mater., 2012, 4: e4.
[83] Qing G Y, Sun T L. Adv. Mater., 2011, 23: 1615.
[84] Zhang M X, Qing G Y, Xiong C L, Cui R, Pang D W, Sun T L. Adv. Mater., 2013, 25: 749.
[85] Asensio J L, Ardá A, Cañada F J, Jiménez-Barbero J. Acc. Chem. Res., 2013, 46: 946.
[86] Schneider H J, Yatsimirsky A. Chem. Soc. Rev., 2008, 37: 263.
[87] Schneider H J, Angew. Chem. Int. Ed., 2009, 48: 3924.
[88] Ito S, Hayama K, Hirabayashi J. Methods Mol. Biol., 2009, 534: 195.

PDF (4147KB)

3520

访问

0

被引

详细

导航
相关文章

/

〈 〉