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化学进展 2006, Vol. 18 Issue (0708): 957-965 前一篇   后一篇

• 综述与评论 •

纤维素衍生物手性固定相研究进展

何永祝1,3;庞浩1,3;廖兵1,2*   

  1. 1.中国科学院广州化学研究所 广州 510650;2.中国科学院纤维素化学重点实验室 广州 510650;3. 中国科学院研究生院 北京 100049
  • 收稿日期:2005-08-01 修回日期:2005-12-01 出版日期:2006-08-24 发布日期:2006-08-24
  • 通讯作者:

    廖兵

Progress in Cellulose-Based Chiral Stationary Phases

Yongzhu He1,3; Hao Pang1,3; Bing Liao1,2*   

  1. 1.Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou 510650, China; 2. Key Laboratory of Cellulose and Lignocellulosics Chemistry, Chinese Academy of Sciences, Guangzhou 510650, China;3. Graduate School of the Chinese Academy of Sciences, Beijing 100049, China
  • Received:2005-08-01 Revised:2005-12-01 Online:2006-08-24 Published:2006-08-24
  • Contact: Bing Liao
本文从用作手性固定相的纤维素衍生物种类、纤维素衍生物手性固定相制备方法及其在高效液相色谱中的应用三个方面介绍了国内外近年来的研究进展, 并展望了该领域今后的研究方向。
The recent progress in the research and development on the kinds of cellulose derivatives using as chiral stationary phases, the types of chiral stationary phases consisting of cellulose derivatives and the application of the chiral stationary phases in high-performance liquid chromatography is reviewed. The trends of research in this field are also proposed. 

中图分类号: 

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[ 1 ] Matthijs N , Perrin C , Heyden Y V , et al . J . Chromatogr. A ,2004 , 1041 (1/2) : 119 —133
[ 2 ] Yashima E. J . Chromatogr. A , 2001 , 906 : 105 —125
[ 3 ] Têrêk G, Goetelen L , Luyckx R. J . Pharmaceut . Biomed. ,2005 , 39(3/4) : 425 —430
[ 4 ] 孟磊(Meng L) , 袁黎明( Yuan L M) . 化学试剂(Chemical Reagents) , 2001 , 23(4) : 220 —223
[ 5 ] Ye Y K, Stringham R W, Wirth M J . J . Chromatogr. A , 2004 ,1057(1/2) : 75 —82
[ 6 ] Okamoto Y, Kawashima M, Yamamoto K, et al . Chem. Lett . ,1984 , 739 —742
[ 7 ] Okamoto Y, Kawashima M. Hatada K, J . Am. Chem. Soc. ,1984 , 106 : 5357 —5359
[ 8 ] Okamoto Y, Aburatani R , Hatada K. J . Chromatogr. A , 1987 ,389 : 95 —102
[ 9 ] Okamoto Y, Kawashima M, Hatada K. J . Chromatogr. A , 1986 ,363 : 173 —186
[10] Chankvetadze B , Yashima E , Okamoto Y. J . Chromatogr. A ,1994 , 670 : 39 —49
[11] Chankvetadze B , Yashima E , Okamoto Y. J . Chromatogr. A ,1995 , 694 : 101 —109
[12] Chankvetadze B , Chankvetadze L , Okamoto Y. J . Chromatogr.A , 1997 , 787 : 67 —77
[13] Yashima E , Fukaya H , Okamoto Y. J . Chromatogr. A , 1994 ,677 : 11 —19
[14] Kaida Y, Okamoto Y. Chirality , 1992 , 4(2) : 122 —124
[15] Kubota T , Yamamoto C , Okamoto Y. Chirality , 2002 , 14 (5) :372 —376
[16] Kubota T , Yamamoto C , Okamoto Y. Chirality , 2004 , 16 (5) :309 —313
[17] Dent C E. Biochem. J . , 1948 , 43 : 169 —180
[18] Kotake M, Sakan T , Senoh S. J . Am. Chem. Soc. , 1951 , 73 :1832 —1834
[19] Dalgliesh C E. J . Chem. Soc. , 1952 , 137 : 3940 —3942
[20] Hesse G, Hagel R. Chromatographia , 1973 , 6 : 277 —280
[21] Hesse G, Hagel R. Liebigs Ann. Chem. , 1976 , 996 —1008
[22] Lindner K R , Mannschreck A. J . Chromatogr. A , 1980 , 193 :308 —310
[23] Schneider M P , Bippi H. J . Am. Chem. Soc. , 1980 , 102 :7363 —7365
[24] Blaschke G. J . Liq. Chromatogr. , 1986 , 9(2/3) : 341 —368
[25] Francotte E. J . Chromatogr. A , 1994 , 666 : 565 —601
[26] Okamoto Y, Yashima E. Angew. Chem. Int . Ed. , 1998 , 37 :1021 —1043
[27] Oguni K, Oda H , Ichida A. J . Chromatogr. A , 1995 , 694 :91 —100
[28] Okamoto Y, Kawashima M, Yamamoto K, et al . Chem. Lett . ,1984 , 739 —742
[29] Ichida A , Shibata T , Okamoto I , et al . Chromatographia , 1984 ,19 : 280 —284
[30] Shibata T , Sei T , Nishimura H. Chromatographia , 1987 , 24 :552 —554
[31] Francotte E , Wolf R M, Lohmann D. J . Chromatogr. , 1985 ,347 : 25 —37
[32] 邵保海(Shao B H) , 徐秀珠(Xu X Z) , 傅小芸(Fu X Y) 等.分析化学(Chinese J . Anal . Chem. ) , 2003 , 31(2) : 239 —244
[33] Yamamoto C , Okamoto Y. Bull . Chem. Soc. Jpn. , 2004 , 77(2) : 227 —257
[34] Belloli E L , Gla?on V , Vaccher C , et al . J . Chromatogr. A ,2002 , 972 (2) : 211 —219
[35] Yashima E , Okamoto Y. Bull . Chem. Soc. Jpn. , 1995 , 68 :3289 —3307
[36] 邵保海(Shao B H) , 徐秀珠(Xu X Z) , 傅小芸(Fu X Y) 等.化学学报(Acta Chimica Sinica) , 2001 , 59 : 1982 —1988
[37] Francotte E , Zhang T. J . Chromatogr. A , 1995 , 718 : 257 —266
[38] 邵保海(Shao B H) , 徐秀珠(Xu X Z) , 傅小芸(Fu X Y) 等.化学学报(Acta Chimica Sinica) , 2003 , 61(10) : 1635 —1640
[39] Goossens J F , Foulon C , Bailly C , et al . Chromatographia , 2004 ,59(5/6) : 305 —313
[40] Cirilli R , Ferretti R , Gallinella B , et al . J . Sep. Sci . , 2005 , 28(7) : 627 —634
[41] Lipka E , Guelzim A , Vaccher C , et al . J . Biochem. Biophy.Meth. , 2005 , 64(1) : 46 —58
[42] Champion W L Jr , Lee J , Garrison W, et al . J . Chromatogr. A ,2004 , 1024 (1/2) : 55 —62
[43] Matthijs N , Rerrin C , Heyden Y V , et al . J . Chromatogr. A ,2004 , 1041 (1/2) : 119 —133
[44] Andersson M E , Aslan D , Clarke A , et al . J . Chromatogr. A ,2003 , 1005 (1/2) : 83 —101
[45] Perrin C , Matthijs N , Heyden Y V , et al . J . Chromatogr. A ,2002 , 966 (1/2) : 119 —134
[46] 徐莉(Xu L) , 刘岚(Liu L) , 邓芹英(Deng Q Y) 等. 中山大学学报(自然科学版) (Acta Scientiarum Naturalium Universitatis Sunyatseni) , 2002 , 41(5) : 115 —117
[47] 徐莉(Xu L) , 何建峰(He J F) , 邓芹英(Deng Q Y) 等. 分析测试学报(Journal of Instrumental Analysis) , 2003 , 22 ( 2) :1 —4
[48] 徐莉(Xu L) , 何建峰(He J F) , 邓芹英(Deng Q Y) 等. 分析化学(Chinese J . Anal . Chem. ) , 2003 , 31(5) : 537 —540
[49] Okamoto Y, Kaida Y. J . High Resol . Chromatogr. , 1990 , 13 :708 —712
[50] Okamoto Y, Kaida Y. J . Chromatogr , A , 1994 , 666 : 403 —419
[51] Yashima E , Yamamoto C , Okamoto Y. Synlett , 1998 , 344 —360
[52] Polcaro C M, Berti A , Viel S , et al . J . Liq. Chromatogr. &Rel . Tech. , 2004 , 27(1) : 49 —61
[53] Leonelli F , Garofalo B , Sinibaldi M, et al . J . Liq. Chromatogr.&Rel . Tech. , 2003 , 26(3) : 409 —424
[54] Péter A , #rki A , Forró E , et al . Chirality , 2005 , 17(4) : 193 —200
[55] Francotte E , Leutert T , La V L , et al . Chirality , 2002 , 14(4) :313 —317
[56] Caccamese S , Caruso C , Parrinello N , et al . J . Chromatogr. A ,2005 , 1076 : 155 —162
[57] Ghanem A , Hoenen H , Aboul-Enein H Y, et al . Anal . Chim.Acta , 2005 , 538 (1/2) : 15 —24
[58] Sousa E P , Tiritan M E , Pinto M M, et al . Chirality , 2004 , 16(5) : 279 —285
[59] 蔡小军(Cai X J) , 徐秀珠(Xu X Z) , 张大同(Zhang D T) 等.分析化学(Chinese J . Anal . Chem. ) , 2004 , 32(2) : 134 —138
[60] 张大同(Zhang D T) , 徐秀珠(Xu X Z) , 蔡小军(Cai XJ) 等.分析化学(Chinese J . Anal . Chem. ) , 2004 , 32(2) : 191 —194
[61] Varim M, Saras S. Chromatographia , 2002 , 56(5P6) : 307 —312
[62] Kasai H F , Tsubuki M, Takahashi K, et al . J . Chromatogr. A ,2002 , 977 (1) : 125 —134
[63] Park T H , Whang Y C , Okamoto Y, et al . J . Sep. Sci . , 2003 ,26(15/16) : 1331 —1336
[64] Zhou Z Q , Wang P , Jiang S R , et al . J . Liq. Chromatogr. & Rel . Tech. , 2003 , 26(17) : 2873 —2880
[65] Sousa E P , Tiritan M E , Pinto M M, et al . Chirality , 2004 , 16(5) : 279 —285
[66] Simenel A A , Kuzmenko Y V , Morozova E A. J . Organomet .Chem. , 2003 , 688 (1/2) : 138 —143
[67] Kim B H , Lee S U , Kim K T , et al . Chirality , 2003 , 15 (3) :276 —283
[68] Mesplet N , Saito Y, Agrofogolio L A , et al . Bioorg. Chem. ,2003 , 31 : 237 —247
[69] Cirilli R , Costi R , Santo D R , et al . J . Chromatogr. A , 2003 ,993(1/2) : 17 —28
[70] Mesplet N , Saito Y, Agrofoglio L A , et al . J . Chromatogr. A ,2003 , 983 (1/2) : 115 —124
[71] Watt A P , Hitzel L , McRtishine R J . J . Biochem. Biophy.Meth. , 2002 , 54(1/3) : 275 —286
[72] Chankvetadze B , Chankvetadze L , Okamoto Y, et al . J .Chromatogr. A , 1997 , 787 : 67 —77
[73] Yashima E , Yamamoto C , Okamoto Y. Polym. J . , 1995 , 27 :856 —861
[74] Kubota T , Yamamoto C , Okamoto Y. J . Am. Chem. Soc. ,2000 , 122 : 4056 —4059
[75] Kubota T , Yamamoto C , Okamoto Y. Chirality , 2002 , 14 (5) :372 —376
[76] Kubota T , Yamamoto C , Okamoto Y. Chirality , 2004 , 16 (5) :309 —313
[77] Kaida Y, Okamoto Y. J . Chromatogr. A , 1993 , 641 : 267 —278
[78] Okamoto Y, Kaida Y, Hayashida H , et al . Chem. Lett . , 1990 ,909 —912
[79] Ikai T , Yamamoto C , Okamoto Y, et al . Chirality , 2005 , 17(6) : 299 —304
[80] Felix G. J . Chromatogr. A , 2001 , 906 : 171 —184
[81] Kaida Y, Okamoto Y. Bull . Chem. Soc. Jpn. , 1993 , 66 :2225 —2232
[82] Chassaing C , Thienpont A , Félix G. J . Chromatogr. A , 1996 ,738 : 157 —167
[83] Acemoglu M, Küsters E , Baumann J , et al . Chirality , 1998 , 10(4) : 294 —306
[84] Francotte E , Zhang T. Analusis Magazine , 1995 , 23 : 13 —20
[85] Francotte E , Zhang T. GITLaborfachzeitschrift , 1996 , 40 : 15 —19
[86] Xiao D S , Hu J W, Zhang M Q , et al . Carbohydr. Res. , 2004 ,339(11) : 1925 —1931
[87] Chen X M, Zou H F , Ni J Y, et al . J . Sep. Sci . , 2003 , 26 :29 —36
[88] Rimbêck K H , Kastner F , Mannschreck A. J . Chromatogr. A ,1986 , 351 : 346 —350
[89] Francotte E , Wolf R M. Chirality , 1991 , 3 : 43 —55
[90] Francotte E , Wolf R M. J . Chromatogr. A , 1992 , 595 : 63 —75
[91] Ikai T , Muraki R , Okamoto Y, et al . Chem. Lett . , 2004 , 33 :1188 —1189
[92] Okamoto Y, Honda S , Yuki H , et al . J . Am. Chem. Soc. ,1981 , 103 : 6971 —6973
[93] 王来来(Wang L L) , 吕士杰(Lü S J) , 李树本(Li S B) 等. 色谱(Chinese Journal of Chromatography) , 1998 , 16 (4) : 285 —288
[94] 侯经国(Hou J G) , 邓启良(Deng Q L) , 孟晓蓉(Meng X R)等. 色谱(Chinese Journal of Chromatography) , 2001 , 19 (2) :154 —156
[95] 敦惠娟(Dun H J ) , 韩小茜(Han X Q) , 陈立仁(Chen L R)等. 分析化学( Chinese J . Anal . Chem. ) , 2003 , 31 ( 8) :901 —905
[96] 敦惠娟(Dun HJ) , 宋秀芹(Song X Q) , 陈立仁(Chen L R)等. 化学学报(Acta Chimica Sinica) , 2003 , 61 (8) : 1326 —1330
[97] 敦惠娟(Dun HJ) , 李永民(Li YM) , 陈立仁(Chen L R) 等.高等学校化学学报(Chemical Journal of Chinese Universities) ,2004 , 25(3) : 451 —453
[98] Zhang T , Kientzy C , Franco P , et al . J . Chromatogr. A , 2005 ,1075(1/2) : 65 —75
[99] Okamoto Y, Aburatani R , Miura S I , et al . J . Liq.Chromatogr. , 1987 , 10(8/9) : 1613 —1628
[100] 陈小明(Chen X M) , 毛希琴(Mao X Q) , 邹汉法(Zou H F)等. 化学学报(Acta Chimica Sinica) , 2002 , 60(1) : 93 —97
[101] Chen X M, Liu Y Q , Zou H F , et al . J . Chromatogr. A , 2003 ,1010 : 185 —194
[102] Kimata K, Tsuboi R , Hosoya K, et al . Anal . Methods Instrum. ,1993 , 1 : 23 —29
[103] Oliveros L , López P , Minguillón C , et al . J . Liq. Chromatogr. ,1995 , 18 : 1521 —1532
[104] Minguillón C , Franco P , Oliveros L , et al . J . Chromatogr. A ,1996 , 728 : 407 —414
[105] Minguillón C , Franco P , Oliveros L , et al . J . Chromatogr. A ,1996 , 728 : 415 —422
[106] Franco P , Minguillón C , Oliveros L , et al . J . Chromatogr. A ,1997 , 791 : 37 —44
[107] Oliveros L , Senso A , Minguillón C , et al . Chirality , 1998 , 10(4) : 283 —288
[108] Franco P , Senso A , Oliveros L , et al . J . Chromatogr. A , 1998 ,796 : 265 —272
[109] Kubota T , Kusano T , Okamoto Y, et al . Chem. Lett . , 2001 ,724 —725
[110] Kubota T , Yamamoto C , Okamoto Y, et al . Chirality , 2003 , 15(1) : 77 —82
[111] Kubota T , Yamamoto C , Okamoto Y. J . Polym. Sci . A: Polym.Chem. , 2003 , 41(22) : 3703 —3712
[112] Kubota T , Yamamoto C , Okamoto Y. J . Polym. Sci . A: Polym.Chem. , 2004 , 42(18) : 4704 —4710
[113] 秦峰(Qin F) , 陈小明(Chen X M) , 邹汉法(Zou H F) 等. 色谱(Chinese Journal of Chromatography) , 2004 , 22 (6) : 569 —574
[114] Chen XM, Qin F , Zou H F. J . Chromatogr. A , 2004 , 1034 (1/2) : 109 —166
[115] Garces J , Franco P , Oliveros L , et al . Tetrahedron : Asymmetry ,2003 , 14(9) : 1179 —1185
[116] Kasuya N , Kusaka Y, Habu N , et al . Cellulose , 2002 , 9(3/4) :263 —269
[117] Francotte E , WO 9 627 615 , 1996
[118] Francotte E , Zhang T. WO 9 704 011 , 1997
[119] Mayer S , Briand X, Francotte E. J . Chromatogr. A , 2000 , 875(1/2) : 331 —339
[120] Francotte E , Huynh D. J . Pharm. Biomed. Anal . , 2002 , 27(3/4) : 421 —429
[121] Franco P , Senso A , Minguillón C , et al . J . Chromatogr. A ,2001 , 906 : 155 —170
[122] Oliveros L. WO 085 000A1 , 2003
[123] Chankvetadze B , Yamamoto C , Okamoto Y. Chem. Lett . , 2003 ,32 : 850 —851
[124] Chankvetadze B , Ikai T , Okamoto Y, et al . J . Chromatogr. A ,2004 , 1042 : 55 —60
[125] Borman P , Boughtflower B , Mutton I , et al . Chirality , 2003 , 15(S1) : S1 —S12
[126] Chen L , Thompson R A , Johnson B D , et al . Chirality , 2002 , 14(5) : 393 —399
[127] Ye Y K, Lynam K G, Stringham R W. J . Chromatogr. A , 2004 ,1041(1/2) : 211 —217
[128] Grobuschek N , Sriphong L , Gübitz G, et al . J . Biochem.Biophy. Meth. , 2002 , 53(1P3) : 25 —36
[129] Chen X M, Jin W H , Zou H F , et al . Electrophoresis , 2003 , 24(15) : 2559 —2566
[130] Chen X M, Qin F , Zou H F , et al . Electrophoresis , 2004 , 25(16) : 2817 —2824
[131] Chankvetadze B , Kartozia I , Yamamoto C , et al . J . Pharm.Biomed. Anal . , 2003 , 30(6) : 1897 —1906
[132] Veciana J , Crespo M I. Angew. Chem. Int . Ed. Engl . , 1991 ,30(1) : 74 —76
[133] Gasparrini F , Acquarica I , Pierini M, et al . J . Sep. Sci . , 2001 ,24(12) : 941 —946
[134] Trapp O , Trapp G, Schurig V. J . Biochem. Biophy. Meth. ,2002 , 54(1/3) : 301 —313
[135] Krupcik J , Oswald P , Májek P , et al . J . Chromatogr. A , 2003 ,1000(1/2) : 779 —800
[136] Cannazza G, Braghiroli D , Parenti C , et al . J . Pharm. Biomed.Anal . , 2000 , 23 : 117 —125
[137] Cannazza G, Braghiroli D , Parenti C , et al . Chirality , 2001 , 13 :94 —101
[138] Tobler E , L?mmerhofer M, Lindner W, et al . Chirality , 2001 , 13(10) : 641 —647
[139] Cirilli R , Costi R , Santo D R , et al . J . Chromatogr. A , 2003 ,993(1/2) : 17 —28
[140] Lorenz K, Yashima E , Okamoto Y. Angew. Chem. Int . Ed. ,1998 , 37(13/14) : 1922 —1925
[141] Trapp O , Schoetz G, Schurig V. Chirality , 2001 , 13 : 403 —414

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