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Progress in Chemistry 2006, Vol. 18 Issue (06): 780-788 Previous Articles   Next Articles

• Review •

Application of Electrospray Ionization Mass Spectrometry in Chiral Recognition and Analysis

Qin Liu;Shuzhen Zhang;Bidong Wu;Rui Shen;Jianwei Xie**;Keliang Liu   

  1. Institute of Pharmacology and Toxicology, The Academy of Military Medical Sciences, Beijing 100850, China
  • Received: Revised: Online: Published:
  • Contact:

    Jianwei Xie

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In recent years, eletrospray ionization mass spectrometry (ESI-MS) has become more and more attractive in chiral analysis due to its advantages such as short analysis time, high sensitivity, simplistity, and small amount of sample. This article reviews the application of eletrospray ionization mass spectrometry in chiral recognition and analysis. Emphasis is put on the different experimental methods and the chiral selectors. The prospect of the application is also discussed.

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[ 1 ] 安登魁(An D K) . 现代药物分析选论( Selected Topics on Modern Pharmaceutical Analysis) . 北京: 中国医药科技出版社(Beijing : Chinese Medical Science and Technology Press) ,2001.4 —102
[ 2 ] Kyba E P , Timko J M, Kaplan L J , et al . J . Am. Chem. Soc. ,1978 , 100 : 4555 —4568
[ 3 ] Tsubaki K, Mukoyoshi K, Morikama H , et al . Chirality , 2002 ,14 : 713 —715
[ 4 ] Wong W L , Huang K H , Teng P F , et al . Chem. Commun. ,2004 , 384 —385
[ 5 ] Zilinsksa A , Stoncius S , Butkus E. Chirality , 2005 , 17 : S70 —S73
[ 5 ] Uncuta C , Caraman G B , Tanase C I , et al . Chirality , 2005 , 17 :63 —72
[ 7 ] Lara K O , Godoy-Alcantar C , Eliseev A V , et al . Org. Biomol .Chem. , 2004 , 2 : 1712 —1718
[ 8 ] Schmidt R , Wahl H G, Hãberle H , et al . Chirality , 1999 , 11 :206 —211
[ 9 ] Desai M J , Armstrong D A , et al . J . Mass Spectrom. , 2004 , 39 :177 —187
[10] Lecnik O , Schmid M G, Presser A , et al . Elecrtophoresis , 2002 ,23 : 3006 —3012
[11] Williams K L , Sander L C , Wise S A. Chirality , 1996 , 8 : 325 —331
[12] Daniel J M, Friess S D , Rajagopalan S , et al . Int . J . Mass Spectrom. , 2002 , 216 : 1 —27
[13] Schalley C A. Mass Spectrom. Rev. , 2001 , 20 : 253 —309
[14] Tao W A , Cooks R G. Anal . Chem. , 2003 , 75 : 25A —31A
[15] Loo J A. Mass. Spectrom. Rev. , 1997 , 16 : 1 —23
[16] Tabet J C. Tetrahedron , 1987 , 43 : 3413 —3420
[17] Hua S M,Chen Y Z ,Jiang L F , et al . Org. Mass Spectrom. ,1986 , 21 : 7 —10
[18] Chen Y Z , Li H , Yang H J , et al . Org. Mass Spectrom. , 1988 ,23 : 821 —824
[19] Yang H J ,Chen Y Z. Org. Mass Spectrom. , 1992 , 27 : 736 —740
[20] Filippi A , Speranza M. Int . J . Mass Spectrom. , 2000 , 199 :211 —219
[21] Mancel V , Sellier N , Lesage D , et al . Int . J . Mass Spectrom. ,2004 , 237 : 185 —195
[22] 陈耀祖(Chen Y Z) , 吴忆南(Wu YN) . 分析化学(Chinese J .Anal . Chem. ) , 1998 , 26 : 737 —741
[23] Sawada M. Mass Spectrom. Rev. , 1997 , 16 : 73 —90
[24] Matsumoto K, Yamamoto C , Yasjoma E , et al . Rapid Comm.Mass Spectrom. , 1999 , 13 : 2011 —2013
[25] Chu I H , Dearden D V , Bradshaw J S , et al . J . Am. Chem.Soc. , 1993 , 115 : 4318 —4320
[26] Dobo A , Liptak M, Vekey K, et al . Rapid Comm. Mass Spectrom. , 1997 , 11 : 889 —896
[27] Sawada M, Okumura Y, Shizuma M, et al . J . Am. Chem. Soc. ,1993 , 115 : 7381 —7388
[28] Sawada M, Shizuma M, Takai Y, et al . J . Am. Chem. Soc. ,1992 , 114 : 4405 —4406
[29] Sawada M, Takai Y, Yamada H , et al . J . Chem. Soc. , Perkin Trans. 2 , 1998 , 2 : 701 —710
[30] Sawada M, Yamaoka H , Takai Y, et al . Int . J . Mass Spectrom. ,1999 , 193 : 123 —130
[31] Shizuma M, Adachi H , Takai Y, et al . Carbohydr. Res. , 2001 ,335 : 275 —281
[32] Sawada M, Yamaoka H , Takai Y, et al . Chem. Comm. , 1998 ,1569 —1570
[33] Smith G, Leary J A. J . Am. Chem. Soc. , 1996 , 118 : 3293 —3294
[34] Hofmeister G, Leary J A. Org. Mass Specrtrom. , 1991 , 26 :811 —812
[35] Vekey K, Czira G. Anal . Chem. , 1997 , 69 : 1700 —1705
[36] Liang Y J , Bradshaw J S , Izatt R M, et al . Int . J . Mass Spectrom. , 1999 , 185/186/187 : 977 —988
[37] Vekey K, Zerilli L F. Org. Mass Spectrom. , 1991 , 26 : 939 —944
[38] Fenselau C , Cotter R J . Chem. Rev. , 1987 , 87 : 501 —512
[39] Filippi A , Giardini A , Piccirillo S , et al . Int . J . Mass Spectrom. , 2000 , 198 : 137 —163
[40] Speranza M. Int . J . Mass Spectrom. , 2004 , 232 : 277 —317
[41] Ramirez J , He F , Lebrilla C B. J . Am. Chem. Soc. , 1998 ,120 : 7387 —7388
[42] Grigorean G, Ramirez J , Lebrilla C B , et al . Anal . Chem. ,2000 , 72 : 4275 —4281
[43] Grigorean G, Lebrilla C B. Anal . Chem. , 2001 , 73 : 1684 —1691
[44] Gal J F , Stone M, Lebrilla C B. Int . J . Mass Spectrom. , 2003 ,222 : 259 —267
[45] Grigorean G, Cong X, Lebrilla C B. Int . J . Mass Spectrom. ,2004 , 234 : 71 —77
[46] Grigorean G, Gronert S , Lebrilla C B. Int . J . Mass Spectrom. ,2002 , 219 : 79 —87
[47] Arakawa R , Kobayashi M, Fukuo T , et al . Rapid Commun. Mass Spectrom. , 2001 , 15 : 685 —689
[48] Cheng Y, Hercules D M. J . Mass Spectrom. , 2001 , 36 : 834 —836
[49] Arakawa R , Kobayashi M. J . Am. Soc. Mass Spectrom. , 2000 ,11 : 804 —808
[50] 宋凤瑞(Song F R) , 刘子阳(Liu Z Y) , 刘淑莹(Liu S Y) 等.分析化学(Chin. J . Anal . Chem. ) , 1999 , 27 : 1000 —1002
[51] Tao W A , Zhang D , Cooks R G, et al . Anal . Chem. , 1999 , 71 :4427 —4429
[52] Tao W A , Zhang D , Cooks R G, et al . J . Am. Chem. Soc. ,2000 , 122 : 10598 —10609
[53] Tao W A , Gozzo F C , Cooks R G. Anal . Chem. , 2001 , 73 :1692 —1698
[54] Wu L , Tao W A , Cooks R G. Anal . Bioanal . Chem. , 2002 ,373 : 618 —627
[55] Zhang D , Tao W A , Cooks R G. Int . J . Mass Spectrom. , 2001 ,204 : 159 —169
[56] Tao W A , Wu L , Cooks R G. J . Med. Chem. , 2001 , 44 :3541 —3544
[57] Angusti D V , Carazza F , Cooks R G, et al . Anal . Chem. ,2002 , 74 : 3458 —3462
[58] Wu L , Meurer E C , Cooks R G. Anal . Chem. , 2004 , 76 :663 —671
[59] Wu L , Tao W A , Cooks R G. J . Mass Spectrom. , 2003 , 38 :386 —393
[60] Wu L , Lemr K, Cooks R G, et al . J . Am. Soc. Mass Spectrom. , 2003 , 14 : 152 —160
[61] Shen W Y, Wong P S H , Cooks R G. Rapid Comm. Mass Spectrom. , 1997 , 11 : 71 —74
[62] Chen J , Zhu C J , Chen Y, Zhao Y F. Rapid Comm. Mass Spectrom. , 2002 , 16 : 1251 —1253
[63] Paladini A , Calcagni C , di Palma T , et al . Chirality , 2001 , 13 :707 —711
[64] Fago G, Filippi A , Giardini A , et al . Angew. Chem. Int . Ed. ,2001 , 40 : 4051 —4054
[65] Scuderi D , Paladini A , Satta M, et al . Int . J . Mass Spectrom. ,2003 , 223/224 : 159 —168
[66] Paladini A , Scuderi D , Lagana A , et al . Int . J . Mass Spectrom. , 2003 , 228 : 349 —358
[67] Nikolaev E N , Denisov E V , Rakov V S , et al . Int . J . Mass Spectrom. , 1999 , 182P183 : 359 —368
[68] Czerwenka C , Lindner W. Rapid Comm. Mass Spectrom. , 2004 ,18 : 2713 —2718
[69] Tsunematsu H , Ikeda H , Hanazono H , et al . J . Mass Spectrom. ,2003 , 38 : 188 —195
[70] Yao Z P , Wan T S M, Kwong K P , et al . Chem. Comm. , 1999 ,2119 —2120
[71] Yao Z P , Wan T S M, Kwong K P , et al . Anal . Chem. , 2000 ,72 : 5383 —5393
[72] Yao Z P , Wan T S M, Kwong K P , et al . Anal . Chem. , 2000 ,72 : 5394 —5401
[73] Schug K A , Lindner W. J . Am. Soc. Mass Spectrom. , 2005 ,16 : 825 —834
[74] Reetz M T , Becker M H , Klein H W, et al . Angew. Chem. Int .Ed. , 1999 , 38 : 1758 —1761
[75] Guo H , Wu J , Finn M G, et al . Angew. Chem. Int . Ed. ,1999 , 38 : 1755 —1758
[76] Gong S N , Camara E , Lebrilla C B , et al . Int . J . Mass Spectrom. , 1999 , 185/186/187 : 401 —412
[77] Camara E , Green M K, Lebrilla C B , et al . J . Am. Chem.Soc. , 1996 , 118 : 8751 —8752
[78] 任士芳(Ren S F) , 王昊阳(Wang H Y) , 郭寅龙( Guo Y L) .化学学报(Acta Chim. Sinica) , 2004 , 62(19) : 1959 —1962
[79] Lu H J , Guo Y L. Anal . Chim. Acta , 2003 , 482 : 1 —7
[80] Lu H J , Guo Y L. J . Am. Soc. Mass Spectrom. , 2003 , 14 :571 —580
[81] Yu C T , Guo Y L , Chen G Q , et al . J . Am. Soc. Mass Spectrom. , 2004 , 15 : 795 —802
[82] Brewer B N , Zu C L , Koscho M E. Chirality , 2005 , 17 : 456 —463
[83] Liu Q , Zhang S Z , Xie J W, et al . Anal . Chem. , 2005 , 77 :5302 —5310

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