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化学进展 2006, Vol. 18 Issue (12): 1660-1667 前一篇   后一篇

• 综述与评论 •

离子液体的制备及其在酶催化反应中的应用

夏咏梅 吴红平 张玥 方云 孙诗雨 石玉刚   

  1. 江南大学 江南大学
  • 收稿日期:2006-05-23 修回日期:2006-05-02 出版日期:2006-12-24 发布日期:2006-12-25

Synthesis and Application of Ionic Liquids in Enzymatic Catalysis

Yongmei Xia Hongping Wu Yue Zhang Yun Fang Shiyu Sun Yugang Shi   

  • Received:2006-05-23 Revised:2006-05-02 Online:2006-12-24 Published:2006-12-25
离子液体,尤其是非水溶性离子液体可以作为一种溶剂或酶的载体用于非水相酶促反应中,也可以用于双相体系中的酶促反应。本文概括性介绍了常见离子液体的制备,总结和讨论了离子液体中酶的活性、稳定性、反应选择性以及各类酶在离子液体中的催化反应行为。离子液体的物性及其与酶的相容性对酶本身及酶促反应都有很大的影响。在非水相酶促反应中,离子液体的极性作用不遵从通常用来判别大多数有机物溶剂行为的规则,比如lgP规则。
Ionic liquids,especially water-insoluble inoic liquids can be served as solvents or enzyme carrier in non-aqueous and biphasic enzymatic reactions. The synthesis of ionic liquids is briefly reviewed. Enzyme properties including the activity, stability and selectivity in ionic liquids are discussed. The biocatalytic behavior of different enzymes in ionic liquids is summarized. The physical properties of ionic liquids and the enzymes tolerance to ionic liquids can affect the enzymes themselves and the enzymatic reactions. Ionic liquids do not fit into most of the standard heuristics that chemists traditionally use to assess and predict solvent behavior, for example, the role of solvent lgP in non-aqueous enzymatic reactions.

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[ 1 ] Wilkes J S , Zaworotko M J . J . Chem. Soc. Chem. Commun. ,1992 , 965 —967
[ 2 ] Mori M, Garcia R G, Belleville M P , Paolucci-Jeanjean D ,Sanchez J . Catalysis Taday , 2005 , 104 (3) : 313 —317
[ 3 ] Lozano P , Diego T , Gmouh S , Vaultier M. Biotechnol . Prog. ,2004 , 20 : 661 —669
[ 4 ] Roberts N J , Seago A , Carey J S , Freer R , Preston C , Lye GJ .Green Chem. , 2004 , 6 : 475 —482
[ 5 ] Nara S J , Harjani J R , Salunkhe M M. Tetrahedron Letters ,2002 , 43 : 2979 —2982
[ 6 ] Rantwijk F V , Lau R M, Sheldon R A. Trends in Biotechnol . ,2003 , 21(3) : 131 —138
[ 7 ] Jain N , Kumar A , Chauhan S , Chauhan S M S. Tetrahedron ,2005 , 61 : 1015 —1060
[ 8 ] Lau R M, Sorgedrager J M, Carrea G, Rantwijk F V. Green Chem. , 2004 , 6 : 483 —487
[ 9 ] Kaar J L , Jesionowski A M, Berberich J A , Moulton R , Russell A J . J . Am. Chem. Soc. , 2003 , 125 (14) : 4125 —4131
[10] Yang Z , Pan W B. Enzyme and Microbial Technol . , 2005 , 37 :19 —28
[11] Park S , Kazlauskas R. Curr. Opin. Biotechnol . , 2003 , 14 :432 —437
[12] Dzyuba S V , Bartsch R A. Angew. Chem. Int . Ed. , 2003 , 42(2) : 148 —150
[13] Reetz M T , Wiesenhêfer W, FranciòG, Leitner W. Adv. Synth.Catal . , 2003 , 345 : 1221 —1228
[14] Lozano P , de Diego T , Vaultier M, Iborra J L. Chem.Commun. , 2002 , 692 —693
[15] 侯玉翠(Hou Y C) , 刘克文(Liu KW) , 杨春梅( Yang C M) ,吴卫泽(Wu W Z) . 化学通报(Chemistry) , 2005 , 68 : 1 —9
[16] Reetz M T , Wiesenhofer W, Francio G, Leitner W. Chem.Commun. , 2002 , 992 —993
[17] 李汝雄(Li R X) , 王建基(Wang J J ) . 化工进展(Chemical Industry and Engineering Progress) , 2002 , 21 (1) : 43 —48
[18] Elaiwi A , Hitchcock P B , Seddon K R , et al . J . Chem. Soc.Dalton Trans. , 1995 , 3467 —3472
[19] Hirao M, Sugimoto H , Ohno H. J . Electrochem. Soc. , 2000 ,147 (11) : 4168 —4172
[20] Suarez P A Z , Dullius J E L , Einloft S , et a11 J . Polyhedron ,1996 , 15 (7) : 1217 —1219
[21] Bonhote P , Dias A , Papageorgiou N , et al . Inorg. Chem. ,1996 , 35 : 1168 —1178
[22] Fuller J , Carlin R T , Osteryoung R A. J . Electrochem. Soc. ,1997 , 144 (11) : 3881 —3885
[23] Holbrey J D , Seddon K R. J . Chem. Soc. Dalton Trans. , 1999 ,2133 —2139
[24] Katayama Y, Dan S , Miura T , et al . J . Electrochem. Soc. ,2001 , 148 : 102 —105
[25] Fuller J , Carlin R T , Haworth H C. Chem. Commun. , 1994 ,299 —230
[26] Dzyuba S V , Bartsch R A. J . Heterocyclic Chem. , 2001 , 38 :265 —268
[27] Huddleston J G, Visser A E , Reichert W M, Willauer H D ,Broker GA , Rogers R D. Green Chem. , 2001 , 3 : 156 —164
[28] Xu D Q , Liu B Y, Luo S P , et al1 Synthesis , 2003 , (17) :2626 —2628
[29] Heintz A , Lehmann J K, Wertz C J . Chem. Eng. Data , 2003 ,48 (3) : 472 —474
[30] Hasan M, Ozhevnikov I V , Siddiqui M R H , et al1 Inorg.Chem. , 1999 , 38 (25) : 5637 —5641
[31] Lall S , Behaj V , Mancheno D , et al . Synthesis , 2002 , (11) :1530 —1540
[32] Varma R S , Namboodiri V V. Chem. Commun. , 2001 , 643 —644
[33] Namboodiri V V , Varma R S. Tetrahedron Letters , 2002 , 43 :5381 —5383
[34] Zell C A , Frevland W. Langmuir , 2003 , 19 (18) : 7445 —7450
[35] Wasserscheid P , Keim W. Angewandte Chemie International Edition , 2000 , 39(21) : 3772 —3789
[36] Hirao M, Ito K, Nishina N , Ohno H. Electrochim. Acta , 2000 ,45 : 1291 —1294
[37] 任强(Ren Q) , 武进(Wu J) , 张军(Zhang J ) 等. 高分子学报(Acta Polymerica Sinica) , 2003 , (3) : 488 —451
[38] Brown R J C , Dyson P J , Ellis D J , Welton T. Chem.Commun. , 2001 , 1862 —1863
[39] Pernak J , Czepukowicz A , Pozniak R. Ind. Eng. Chem. Res. ,2001 , 40 : 2379 —2383
[40] Hagiwara R , Hirashige T , Tsuda T , et al . J . Electrochem. Soc. ,2002 , 149 : 1 —6
[41] Visser A E , Swatloski R P , Reichert WM, et al . Environ. Sci .Technol . , 2002 , 36 : 2523 —2529
[42] Bates E D , Mayton R D , Ntai L , et al . J . Am. Chem. Soc. ,2002 , 124 (6) : 926 —927
[43] Huddleston J G, Willauer H D , Rogers R D , et al . Chem.Commun. , 1998 , 1765 —1766
[44] Ronald A C , Lowell A K, Richard EL , John C N , Charles L H.J . Am. Chem. Soc. , 1979 , 126 (10) : 1644 —1650
[45] Khadilkar B M, Rebeiro G. Org. Pro. Res. Dev. , 2002 , 6 (6) :826 —828
[46] Park S , Kazlauskas R J . J . Org. Chem. , 2001 , 66 ( 25) :8395 —8401
[47] Abbott A P , Davies D L. Chem. Commun. , 2001 , 2010 —2011
[48] Sherif F G, Shyu L J , Lacroix P M, et al . US 5 731 101 , 1998
[49] Knifton J F. J . Mo11 Catal . , 1987 , 43 : 65 —77
[50] Wasserscheid P , Bosmann A , Bolm C. Chem. Commun. , 2002 ,200 —201
[51] Levillain J , Dubant G, Abrunhosa I , et a11 Chemical Commun. ,2003 , 2914 —2915
[52] 石顺存(Shi S C) , 易平贵(Yi P G) , 曹晨忠(Cao C Z) , 王学业(Wang X Y) , 苏界殊(Su J S) , 刘军喜(Liu J X) . 化工学报(J . Chem. Ind. Eng. ) , 2005 , (6) : 1112 —1119
[53] 张青山(Zhang Q S) , 刘爱霞(Liu A X) , 郭炳南(Guo B N) ,吴锋(Wu F) . 高等学校化学学报(Chemical Journal of Chinese Universities) , 2005 , (2) : 340 —342
[54] 段海峰(Duan H F) , 张所波(Zhang S B) , 林英杰(Lin Y J ) ,邱志明(Qiu Z M) , 王宗睦(Wang ZM) . 高等学校化学学报(Chemical Journal of Chinese Universities) , 2003 , (11) : 2024 —2026
[55] Seddon K R. J . Chem. Tech. Biotechnol . , 1997 , 68 : 351 —356
[56] Laane C , Boeren S , Vos K. Biotechnol . Bioengl . , 1987 , 30 :81 —87
[57] Yang Z , Russell A J . Enzymatic Reactions in Organic Media (eds. Koskinen A M P , Klibanov A M) . London : Blackie Academic &Professional , 1996 , 43 —69
[58] Park S , Viklund F , Hult K, Kazlauskas R J . ACS Symposium Series (eds. Rogers R D , Seddon K R) , 2003 , 856 : 225 —238
[59] Heintz A , Klasen D , Lehmann J K. J . Solution Chem. , 2002 ,31 : 467 —476
[60] Lozano P , de Diego T , Guegan J P , Vaultier M, Iborra J L.Biotechnol . Bioeng. , 2001 , 75 : 563 —569
[61] Maruyama T , Nagasawa S , Goto M. Biotechnol . Lett . , 2002 ,24 : 1341 —1345
[62] Turner M B , Spear S K, Huddleston J G, Holbrey J D , Rogers R D. Green Chem. , 2003 , 5 : 443 —447
[63] Turner M B , Spear S K, Holbrey J D , Rogers R D.Biomacromolecules , 2004 , 5 : 1379 —1384
[64] EcKstein M, Sesing M, Kragl U , Adlercreutz P. Biotechnol .Lett . , 2002 , 24 : 867 —872
[65] Kaar J , Jesionwski A M, Berberich J A , Moulton R , Russell AJ .J . Am. Chem. Soc. , 2003 , 125 : 4125 —4131
[66] Kaftzik N , Wasserscheid P , Kragl U. Organ. Pro. Res. Dev. ,2002 , 6 : 553 —557
[67] Erbeldinger M, Mesiano A J , Russell A J . Biotechnol . Prog. ,2000 , 16 : 1129 —1131
[68] Sheldon R A , Lau R M, Sorgedrager M J , van Rantwijk F ,Seddon K R. Green Chem. , 2002 , 4 : 147 —151
[69] Magnuson D K, Bodley J W, Evans D F. J . Solution Chem. ,1984 , 13 : 583 —587
[70] Sanfilippo C , Antona N D , Nicolosi G. Biotechnol . Lett . , 2004 ,26 : 1815 —1819
[71] Schofer S H , Kaftzik N , Wasserscheid P , Kragl U. Chem.Commun. , 2001 , 425 —426
[72] Eckstein M, Wasserscheid P , Kragl U. Biotechnol . Lett . , 2002 ,24 : 763 —767
[73] Kielbasinski P , Albrycht M, Luczak J , Mikolajczyk M.Tetrahedron : Asymmetry , 2002 , 13 : 735 —738
[74] Ulbert O , Frater T , Belafi-Bako K, Gubicza L. J . Mol . Catal .B : Enzym. , 2004 , 31 : 39 —45
[75] Kim M J , Choi M Y, Lee J K, Ahn Y. J . Mol . Catal . B :Enzym. , 2003 , 26 (326) : 115 —118
[76] Lau R M, Rantwijk F V , Sheddon K R , Sheldon R A. Org.Lett . , 2000 , 2 : 4189 —4191
[77] Itoh T , Akasaki E , Kudo K, Shirakami S. Chem. Lett . , 2001 ,262 —263
[78] Xin J Y, Zhao YJ , Shi Y G, Xia C G, Li S B. World Journal of Microbiology &Biotechnol . , 2005 , 21 : 193 —199
[79] Zhao H , Malhotra S V. Biotechnol . Lett . , 2002 , 24 : 1257 —1260
[80] Hinckley G, Mozhaev V V , Budde C , Khmelnitsky Y L.Biotechnol . Lett . , 2000 , 24 (10) : 2083 —2087
[81] Okrasa K, Guibe-Jampel E , Therisod M. Tetrahedron :Asymmetry , 2003 , 14 (17) : 2487 —2490
[82] Howarth J , Jame P , Dai J F. Tetrahedron Lett . , 2001 , 42 :7517 —7519
[83] 吴红平(Wu H P) . 江南大学学士论文(Bacheloral Dissertation of Southern Yangtze University) , 2004
[84] Blanchard L A , Hancu D , Beckman E J , Brennecke J F. Nature ,1999 , 399 : 28 —29
[85] Blanchard L A , Gu Z , Brennecke J F. J . Phys. Chem. B , 2001 ,105 : 2437 —2444
[86] Laszlo J A , Compton D L. Biotechnol . Bioeng. , 2001 , 75 (2) :181 —186

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