核磁共振波谱在分析化学领域应用的新进展

doi:10.6023/A12060339

摘要/Abstract

发展检测物质的化学组成、结构及其变化的新方法、新技术是分析化学的核心科学问题之一. 波谱分析(光谱、质谱及核磁共振)是分析化学中常用的主要仪器分析手段. 核磁共振能在液态、固态和气态条件下提供复杂体系中分子组成、原子分辨的三维结构、相互作用和动态过程等丰富信息, 在生物分析中发挥着越来越重要的作用. 本文将综合阐述核磁共振技术在生物大分子体系、复杂体系以及与其他分析手段联用的进展情况.

关键词: 核磁共振, 分析化学, 复杂体系, 生物大分子

Development of new and effective methods for measuring chemical composition, molecular structures, interactions and dynamics is one of the major issues of analytical chemistry. Spectral analysis (spectroscopy, mass spectrometry and nuclear magnetic resonance) is the most commonly used analytical tool to address these issues. Nuclear magnetic resonance is capable to determine structure for small molecules, macromolecules and complicated biological systems, and it is considered as the most powerful tool in analytical chemistry. This paper reviewed recent progress of nuclear magnetic resonance in biological macromolecules system, complex system and the hyphenated method applications in analytical chemistry. In the first part, we gave a brief introduction of nuclear magnetic resonance technology and its applications in analytical chemistry field. The detailed application descriptions of nuclear magnetic resonance technology have been summarized from part two to part four. In the second part, we summarized the applications of nuclear magnetic resonance technology in biological macromolecules system, including the main nuclear magnetic resonance technology development in three dimensional protein structural analysis field and its applications; the related methods and applications in the dynamic study of protein complex, the in-cell nuclear magnetic resonance labeling methods development history and its applications, and also the methods of nuclear magnetic resonance technologies in studying the interactions of protein and drugs. In the third part, the qualitative and quantitative analysis of nuclear magnetic resonance technologies in complex systems has been summarized, including the applications in the metabolomics and the applications in the field of food quality and safety. In the fourth part, we briefly introduced the joint applications of magnetic resonance technologies and other separation methods such as chromatography and spectroscopic ways. The conclusions of nuclear magnetic resonance technology applications and the suggestions of future developing directions were stated in the last part.

Key words: nuclear magnetic resonance, analytical chemistry, complex system, biomacromolecules

引用此文

王桂芳, 马廷灿, 刘买利. 核磁共振波谱在分析化学领域应用的新进展[J]. 化学学报, 2012, 70(19): 2005-2011.

Wang Guifang, Ma Tingcan, Liu Maili. Recent Progress in the Nuclear Magnetic Resonance Applications in Analytical Chemistry[J]. Acta Chimica Sinica, 2012, 70(19): 2005-2011.

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参考文献

[1] Williamson, M. P.; Havel, T. F.; Wuthrich, K. J. Mol. Biol. 1985, 182, 295.

[2] Arseniev, A. S.; Wider, G.; Joubert, F. J.; Wuthrich, K. J. Mol. Biol. 1982, 159, 323.

[3] Billeter, M.; Braun, W.; Wuthrich, K. J. Mol. Biol. 1982, 155, 321.

[4] Wagner, G.; Wuthrich, K. J. Mol. Biol. 1982, 155, 347.

[5] Wider, G.; Lee, K. H.; Wuthrich, K. J. Mol. Biol. 1982, 155, 367.

[6] Wuthrich, K. Biochem. Soc. Symp. 1982, 17.

[7] Wuthrich, K. S. Afr. J. Sci. 1982, 78, 381.

[8] Wuthrich, K. Umschau Das Wissenschaftsmagazin 1982, 82, 684.

[9] Wuthrich, K.; Wider, G.; Wagner, G.; Braun, W. J. Mol. Biol. 1982, 155, 311.

[10] Pervushin, K.; Riek, R.; Wider, G.; Wuthrich, K. Proc. Natl. Acad. Sci. 1997, 94, 12366.

[11] Salzmann, M.; Pervushin, K.; Wider, G.; Senn, H.; Wuthrich, K. Proc. Natl. Acad. Sci. 1998, 95, 13585.

[12] Zhu, G.; Yao, X. J. Prog. Nucl. Mag. Res. Sp. 2008, 52, 49.

[13] Riek, R.; Wider, G.; Pervushin, K.; Wuthrich, K. Proc. Natl. Acad. Sci. 1999, 96, 4918.

[14] Takahashi, H.; Nakanishi, T.; Kami, K.; Arata, Y.; Shimada, I. Nat. Struct. Biol. 2000, 7, 220.

[15] Tjandra, N.; Bax, A. Science 1997, 278, 1697.

[16] Tolman, J. R.; Flanagan, J. M.; Kennedy, M. A.; Prestegard, J. H. Proc. Natl. Acad. Sci. 1995, 92, 9279.

[17] Barbieri, R.; Luchinat, C.; Parigi, G. ChemPhysChem 2004, 5, 797.

[18] Bertini, I.; Luchinat, C.; Piccioli, M. In Nuclear Magnetic Resonance of Biological Macromolecules, Pt. B, Vol. 339, Eds.: James, T. L.; Dotsch V.; Schmitz U., Academic Press, San Diego, 2001, p. 314.

[19] Tang, C.; Schwieters, C. D.; Clore, G. M. Nature 2007, 449, 1078.

[20] Berardi, M. J.; Shih, W. M.; Harrison, S. C.; Chou, J. J. Nature 2011, 476, 109.

[21] Tugarinov, V.; Kay, L. E. J. Am. Chem. Soc. 2003, 125, 13868.

[22] Kainosho, M.; Torizawa, T.; Iwashita, Y.; Terauchi, T.; Ono, A. M.; Guntert, P. Nature 2006, 440, 52.

[23] Tugarinov, V.; Choy, W. Y.; Orekhov, V. Y.; Kay, L. E. Proc. Natl. Acad. Sci. 2005, 102, 622.

[24] Goto, N. K.; Gardner, K. H.; Mueller, G. A.; Willis, R. C.; Kay, L. E. J. Biomol. NMR 1999, 13, 369.

[25] Foster, P.; McElroy, A.; Amero, C. D. Biochemistry-US 2007, 46, 331.

[26] Fernandez, C.; Wuthrich, K. FEBS Lett. 2003, 555, 144.

[27] Fiaux, J.; Bertelsen, E. B.; Horwich, A. L.; Wuthrich, K. Nature 2002, 418, 207.

[28] Fernandez, C.; Adeishvili, K.; Wuthrich, K. Proc. Natl. Acad. Sci. 2001, 98, 2358.

[29] Hilty, C.; Fernandez, C.; Wider, G.; Wuthrich, K. J. Biomol. NMR 2002, 23, 289.

[30] Hilty, C.; Wider, G.; Fernandez, C.; Wuthrich, K. J. Biomol. NMR 2003, 27, 377.

[31] Fernandez, C.; Hilty, C.; Wider, G.; Guntert, P.; Wuthrich, K. J. Mol. Biol. 2004, 336, 1211.

[32] Xu, Y. Q.; Lin, Z.; Ho, C.; Yang, D. W. J. Am. Chem. Soc. 2005, 127, 11920.

[33] Xu, Y. Q.; Zheng, Y.; Fan, J. S.; Yang, D. W. Nat. Methods 2006, 3, 931.

[34] Snyder, D. A.; Xu, Y. Q.; Yang, D. W.; Bruschweiler, R. J. Am. Chem. Soc. 2007, 129, 14126.

[35] Feng, W.; Pan, L.; Zhang, M. Sci. Chin. Life Sci. 2011, 54, 101.

[36] Ikura, M.; Bax, A. J. Am. Chem. Soc. 1992, 114, 2433.

[37] Korzhnev, D. M.; Salvatella, X.; Vendruscolo, M.; Di Nardo, A. A.; Davidson, A. R.; Dobson, C. M.; Kay, L. E. Nature 2004, 430, 586.

[38] Sugase, K.; Dyson, H. J.; Wright, P. E. Nature 2007, 447, 1021.

[39] Korzhnev, D. M.; Religa, T. L.; Banachewicz, W.; Fersht, A. R.; Kay, L. E. Science 2010, 329, 1312.

[40] Farber, P.; Darmawan, H.; Sprules, T.; Mittermaier, A. J. Am. Chem. Soc. 2010, 132, 6214.

[41] Zimmerman, S. B.; Trach, S. O. J. Mol. Biol. 1991, 222, 599.

[42] Serber, Z.; Dotsch, V. Biochemistry-US 2001, 40, 14317.

[43] Llinas, M.; Wuthrich, K.; Schwotzer, W.; Philipsborn, W. V. Nature 1975, 257, 817.

[44] Reckel, S.; Hansel, R.; Lohr, F.; Dotsch, V. Prog. Nucl. Mag. Res. Sp. 2007, 51, 91.

[45] Sharaf, N. G.; Barnes, C. O.; Charlton, L. M.; Young, G. B.; Pielak, G. J. J. Magn. Reson. 2010, 202, 140.

[46] Augustus, A. M.; Reardon, P. N.; Spicer, L. D. Proc. Natl. Acad. Sci. 2009, 106, 5065.

[47] Banci, L.; Barbieri, L.; Bertini, I.; Cantini, F.; Luchinat, E. Plos One 2011, 6.

[48] Barnes, C. O.; Monteith, W. B.; Pielak, G. J. Chembiochem 2011, 12, 390.

[49] Bertini, I.; Felli, I. C.; Gonnelli, L.; Kumar, M. V. V.; Pierattelli, R. Angew. Chem. Int. Ed. 2011, 50, 2339.

[50] Li, C. G.; Wang, G. F.; Wang, Y. Q.; Creager-Allen, R.; Lutz, E. A.; Scronce, H.; Slade, K. M.; Ruf, R. A. S.; Mehl, R. A.; Pielak, G. J. J. Am. Chem. Soc. 2010, 132, 321.

[51] Wang, G. F.; Li, C. G.; Pielak, G. J. Protein Sci. 2010, 19, 1686.

[52] Sakakibara, D.; Sasaki, A.; Ikeya, T.; Hamatsu, J.; Hanashima, T.; Mishima, M.; Yoshimasu, M.; Hayashi, N.; Mikawa, T.; Walchli, M.; Smith, B. O.; Shirakawa, M.; Guntert, P.; Ito, Y. Nature 2009, 458, 102.

[53] Inomata, K.; Ohno, A.; Tochio, H.; Isogai, S.; Tenno, T.; Nakase, I.; Takeuchi, T.; Futaki, S.; Ito, Y.; Hiroaki, H.; Shirakawa, M. Nature 2009, 458, 106.

[54] Selenko, P.; Serber, Z.; Gade, B.; Ruderman, J.; Wagner, G. Proc. Natl. Acad. Sci. 2006, 103, 11904.

[55] Bodart, J. F.; Wieruszeski, J. M.; Amniai, L.; Leroy, A.; Landrieu, I.; Rousseau-Lescuyer, A.; Vilain, J. P.; Lippens, G. J. Magn. Reson. 2008, 192, 252.

[56] Smet, C.; Leroy, A.; Sillen, A.; Wieruszeski, J. M.; Landrieu, I.; Lippens, G. Chembiochem 2004, 5, 1639.

[57] Charlton, L. M.; Pielak, G. J. Proc. Natl. Acad. Sci. 2006, 103, 11817.

[58] Crowley, P. B.; Chow, E.; Papkovskaia, T. Chembiochem 2011, 12, 1043.

[59] Wang, Q. H.; Zhuravleva, A.; Gierasch, L. M. Biochemistry-US 2011, 50, 9225.

[60] Shuker, S. B.; Hajduk, P. J.; Meadows, R. P.; Fesik, S. W. Science 1996, 274, 1531.

[61] Peng, J. W.; Moore, J.; Abdul-Manan, N. Prog. Nucl. Mag. Res. Sp. 2004, 44, 225.

[62] Dalvit, C.; Pevarello, P.; Tato, M.; Veronesi, M.; Vulpetti, A.; Sundstrom, M. J. Biomol. NMR 2000, 18, 65.

[63] Mayer, M.; Meyer, B. Angew. Chem. Int. Ed. 1999, 38, 1784.

[64] Ji, Z. S.; Yao, Z. X.; Liu, M. L. Anal. Biochem. 2009, 385, 380.

[65] Benie, A. J.; Moser, R.; Bauml, E.; Blaas, D.; Peters, T. J. Am. Chem. Soc. 2003, 125, 14.

[66] Mayer, M.; James, T. L. J. Am. Chem. Soc. 2002, 124, 13376.

[67] Klein, J.; Meinecke, R.; Mayer, M.; Meyer, B. J. Am. Chem. Soc. 1999, 121, 5336.

[68] Nicholson, J. K.; Lindon, J. C.; Holmes, E. Xenobiotica 1999, 29, 1181.

[69] Liu, M.; Nicholson, J. K.; Lindon, J. C.; Sanderson, P. N.; Tranter, G. E. Magn. Reson. Chem. 1996, 34, 865.

[70] Wold, S.; Esbensen, K.; Geladi, P. Chemometr. Intell. Lab. Syst. 1987, 2, 37.

[71] Castellani, F.; van Rossum, B.; Diehl, A.; Schubert, M.; Rehbein, K.; Oschkinat, H. Nature 2002, 420, 98.

[72] Li, M.; Wang, B. H.; Zhang, M. H.; Rantalainen, M.; Wang, S. Y.; Zhou, H. K.; Zhang, Y.; Shen, J.; Pang, X. Y.; Zhang, M. L.; Wei, H.; Chen, Y.; Lu, H. F.; Zuo, J.; Su, M. M.; Qiu, Y. P.; Jia, W.; Xiao, C. N.; Smith, L. M.; Yang, S. L.; Holmes, E.; Tang, H. R.; Zhao, G. P.; Nicholson, J. K.; Li, L. J.; Zhao, L. P. Proc. Natl. Acad. Sci. 2008, 105, 2117.

[73] Clayton, T. A.; Lindon, J. C.; Cloarec, O.; Antti, H.; Charuel, C.; Hanton, G.; Provost, J. P.; Le Net, J. L.; Baker, D.; Walley, R. J.; Everett, J. R.; Nicholson, J. K. Nature 2006, 440, 1073.

[74] Nicholson, J. K.; Holmes, E.; Wilson, I. D. Nat. Rev. Microbiol. 2005, 3, 431.

[75] Holmes, E.; Loo, R. L.; Stamler, J.; Bictash, M.; Yap, I. K. S.; Chan, Q.; Ebbels, T.; De Iorio, M.; Brown, I. J.; Veselkov, K. A.; Daviglus, M. L.; Kesteloot, H.; Ueshima, H.; Zhao, L. C.; Nicholson, J. K.; Elliott, P. Nature 2008, 453, 396.

[76] Nicholson, J. K.; Connelly, J.; Lindon, J. C.; Holmes, E. Nat. Rev. Drug Discov. 2002, 1, 153.

[77] Wang, Y. L.; Holmes, E.; Nicholson, J. K.; Cloarec, O.; Chollet, J.; Tanner, M.; Singer, B. H.; Utzinger, J. Proc. Natl. Acad. Sci. 2004, 101, 12676.

[78] Solanky, K. S.; Bailey, N. J.; Beckwith-Hall, B. M.; Bingham, S.; Davis, A.; Holmes, E.; Nicholson, J. K.; Cassidy, A. J. Nutr. Biochem. 2005, 16, 236.

[79] Wang, Y. L.; Tang, H. R.; Nicholson, J. K.; Hylands, P. J.; Sampson, J.; Holmes, E. J. Agric. Food Chem. 2005, 53, 191.

[80] Bertram, H. C.; Andersen, R. H.; Andersen, H. J. Meat Sci. 2007, 75, 128.

[81] Lucas, T.; Quellec, S.; Le Bail, A.; Davenel, A. J. Food Eng. 2005, 70, 151.

[82] Kuo, M. I.; Gunasekaran, S.; Johnson, M.; Chen, C. J. Dairy Sci. 2001, 84, 1950.

[83] Rudi, T.; Guthausen, G.; Burk, W.; Reh, C. T.; Isengard, H. D. Food Chem. 2008, 106, 1375.

[84] Kiokias, S.; Reszka, A. A.; Bot, A. Int. Dairy J. 2004, 14, 287.

[85] Bertram, H. C.; Wiking, L.; Nielsen, J. H.; Andersen, H. J. Int. Dairy J. 2005, 15, 1056.

[86] Ruan, R.; Long, Z.; Chen, P.; Huang, V.; Almaer, S.; Taub, I. J. Food Sci. 1999, 64, 6.

[87] Pitombo, R. N. M.; Lima, G. A. M. R. J. Food Eng. 2003, 58, 59.

[88] Atichokudomchai, N.; Varavinit, S.; Chinachoti, P. Carbohydr. Polym. 2004, 58, 383.

[89] Tananuwong, K.; Reid, D. S. Carbohydr. Polym. 2004, 58, 345.

[90] Elomaa, M.; Asplund, T.; Soininen, P.; Laatikainen, R.; Peltonen, S.; Hyvarinen, S.; Urtti, A. Carbohydr. Polym. 2004, 57, 261.

[91] Wang, L.; Li, Y.; Hu, J. H. Chin. Oils Fats 2008, 75. (王乐, 黎勇, 胡健华, 中国油脂, 2008, 75.)

[92] Han, X. L.; Zhang, W. J.; Wang, D. L.; Wang, Y. J.; L. H. Liquor-Making Sci. & Technol. 2009, 112. (韩兴林, 张五九, 王德良, 王异静, 李红, 酿酒科技, 2009, 112.)

[93] Bayer, E.; Albert, K.; Nieder, M.; Grom, E.; Wolff, G.; Rindlisbacher, M. Anal. Chem. 1982, 54, 1747.

[94] Fyfe, C. A.; Cocivera, M.; Damji, S. W. H.; Hostetter, T. A.; Sproat, D.; Obrien, J. J. Magn. Reson. 1976, 23, 377.

[95] Haw, J. F.; Glass, T. E.; Hausler, D. W.; Motell, E.; Dorn, H. C. Anal. Chem. 1980, 52, 1135.

[96] Benfenati, E.; Pierucci, P.; Fanelli, R.; Preiss, A.; Godejohann, M.; Astratov, M.; Levsen, K.; Barcelo, D. J. Chromatogr. A 1999, 831, 243.

[97] Exarchou, V.; Godejohann, M.; van Beek, T. A.; Gerothanassis, I. P.; Vervoort, J. Anal. Chem. 2003, 75, 6288.

[98] Godejohann, M.; Tseng, L. H.; Braumann, U.; Fuchser, J.; Spraul, M. J. Chromatogr. A 2004, 1058, 191.

[99] Frydman, L.; Scherf, T.; Lupulescu, A. Proc. Natl. Acad. Sci. 2002, 99, 15858.

[100] Kim, S.; Szyperski, T. J. Am. Chem. Soc. 2003, 125, 1385.

[101] Kupce, E.; Freeman, R. J. Biomol. NMR 2003, 27, 383.

[102] Schanda, P.; Brutscher, B. J. Am. Chem. Soc. 2005, 127, 8014.

[103] Szyperski, T.; Yeh, D. C.; Sukumaran, D. K.; Moseley, H. N. B.; Montelione, G. T. Proc. Natl. Acad. Sci. 2002, 99, 8009.

[104] Foxall, P. J. D.; Lenz, E. M.; Lindon, J. C.; Neild, G. H.; Wilson, I. D.; Nicholson, J. K. Ther. Drug Monit. 1996, 18, 498.

[105] Nicholls, A. W.; Lindon, J. C.; Farrant, R. D.; Shockcor, J. P.; Wilson, I. D.; Nicholson, J. K. J. Pharmaceut. Biomed. 1999, 20, 865.

[106] Spraul, M.; Hofmann, M.; Lindon, J. C.; Farrant, R. D.; Seddon, M. J.; Nicholson, J. K.; Wilson, I. D. NMR Biomed. 1994, 7, 295.

[107] Xiao, H. B.; Krucker, M.; Putzbach, K.; Albert, K. J. Chromatogr. A 2005, 1067, 135.

[108] Harrigan, G. G.; Goetz, G. H. Comb. Chem. High Throughput Screen 2005, 8, 529.

[109] Keifer, P. A. Magn. Reson. Chem. 2003, 41, 509.

[110] Keifer, P. A.; Smallcombe, S. H.; Williams, E. H.; Salomon, K. E.; Mendez, G.; Belletire, J. L.; Moore, C. D. J. Comb. Chem. 2000, 2, 151.

[111] Shapira, B.; Karton, A.; Aronzon, D.; Frydman, L. J. Am. Chem. Soc. 2004, 126, 1262.

[112] Zhou, Z. M.; Zhang, W. L.; Zhang, X.; Ye, C.; Liu, M. L. In The Abstracts of the 14th National Spectroscopy Conference, 2006. (周志明, 张维农, 张许, 叶朝辉, 刘买利, In 第十四届全国波谱学学术会议论文摘要集, 2006.)