Progresses in Matrixed Chromatographic NMR

doi:10.11938/cjmr20150415

Abstract

Abstract:

Diffusion ordered NMR spectroscopy (DOSY), sometimes also known as chromatographic NMR (CNMR), is a powerful tool for analyzing complex mixture. However, it is often difficult to distinguish components having similar molecular properties using only the diffusion characteristics. A practical way to solve this problem is adding some matrices, such as silica gel or polymers into magic angle spinning rotor or NMR tube, as the virtual stationary phase (VSP), to increase the difference in diffusion rate among different components. Matrix aided CNMR has been shown to have improved discriminating capability when analyzing complex mixtures. In this paper, recent progresses in the field of matrixed CNMR were reviewed.

Key words: DOSY, self-diffusion coefficient, matrix, chromatographic NMR

CLC Number:

O482.53

HE Bao-jiang1， XU Xiu-juan1， YANG Wei-ping1， ZHANG Wen-juan1， WU Rui3， HUANG Shao-hua2*， YANG Ying2， BAI Zheng-wu3*. Progresses in Matrixed Chromatographic NMR[J]. Chinese Journal of Magnetic Resonance, 2015, 32(4): 699-706.

References

[1] Viel S, Ziarelli F, Caldarelli S. Enhanced diffusion-edited NMR spectroscopy of mixtures using chromatographic stationary phases[J]. Proc Natl Acad Sci USA, 2003, 100(17): 9 696－9 698.

[2] Albert K. On-Line LC-NMR and Related Techniques[M]. West Sussex: John Wiley & Sons, Ltd, 2002.

[3] Mao X(毛希安). Practical Techniques and Application in Modern Nuclear Magnetic Resonanc(现代核磁共振实用技术及应用)[M]. Beijing(北京): Science and Technology Literature Press(科学技术文献出版社), 1999.

[4] Johnson C S. Diffusion ordered nuclear magnetic resonance spectroscopy: principles and applications[J]. Prog Nucl Magn Reson Spectrosc, 1999, 34(3-4): 203－256.

[5] Price K E, Lucas L H, Larive C K. Analytical applications of NMR diffusion measurements[J]. Anal Bioanal Chem, 2004, 378(6): 1 405－1 407.

[6] Gounarides J S, Chen A D, Shapiro M J. Nuclear magnetic resonance chromatography: Applications of pulse field gradient diffusion NMR to mixture analysis and ligand-receptor interactions[J]. J Chromatogr B, 1999, 725(1): 79－90.

[7] Stockman B J, Dalvit C. NMR screening techniques in drug discovery and drug design[J]. Prog Nucl Magn Reson Spectrosc, 2002, 41(3, 4): 187－231.

[8] Caldarelli S. Chromatographic NMR: A tool for the analysis of mixtures of small molecules[J]. Magn Reson Chem, 2007, 45(S1): S48－S55.

[9] Novoa-Carballal R, Fernandez-Megia E, Jimenez C, et al. NMR methods for unravelling the spectra of complex mixtures[J]. Nat Prod Rep, 2011, 28(1): 78－98.

[10] Pages G, Delaurent C, Caldarelli S. Simplified analysis of mixutres of small molecules by chromatographic NMR Spectroscopy[J]. Angew Chem Int Ed, 2006, 45(36): 5 950－5 953.

[11] Hoffman R E, Arzuan H, Pemberton C, et al. High-resolution NMR “chromatography” using a liquids spectrometer[J]. J Magn Reson, 2008, 194(2): 295－299.

[12] Li G B, Yu X Y, Zheng B S, et al. NMR studies on interactions between diperoxovanadate and N-substituted picolinamide[J]. Acta Chim Sin, 2007, 65(21): 2 357－2 362.

[13] Kavakka J S, Kilpelainen I, Heikkinen S. General chromatographic NMR method in liquid state for synthetic chemistry: Polyvinylpyrrolidone assisted DOSY experiments[J]. Org Lett, 2009, 11(6): 1 349－1 352.

[14] Pelta M D, Barjat H, Morris G A, et al. Pulse sequences for high-resolution diffusion-ordered spectroscopy (HR-DOSY) [J]. Magn Reson Chem, 1998, 36(10): 706－714.

[15] Carr H Y, Purcell E M. Effects of diffusion on free precession in nuclear magnetic resonance experiments[J]. Phys Rev, 1954, 94(3): 630－638.

[16] Meiboom S, Gill D. Modified spin-echo method for measuring nuclear relaxation times[J]. Rev SciInstrum 1958, 29(8): 688－691.

[17] Kavakka J S, Parviainen V, Wahala K, et al. Enhanced chromatographic NMR with polyethyleneglycol. A novel resolving agent for diffusion ordered spectroscopy[J]. Magn Reson Chem, 2010, 48(10): 777－781.

[18] Huang S, Gao J, Wu R, et al. Polydimethylsiloxane: A general matrix for high-performance chromatographic NMR spectroscopy[J]. Angew Chem Int Ed, 2014, 53(9): 11 582－11 595.

[19] Wu Rui(吴瑞), Bai Zheng-wu(柏正武), Yang Ying(杨盈), et al. Study of the separation performance of PDMS matrixed chromatographic NMR technique(基于PDMS的NMR中色谱技术的分离性能研究)[J]. Chinese J Magn Reson(波谱学杂志), 2015, 32(3): 511－517.

[20] Zielinski M E, Morris K F. Using perdeuterated surfactant micelles to resolve mixture components in diffusion-ordered NMR spectroscopy[J]. Magn Reson Chem, 2009, 47(1): 53－56.

[21] Evans R, Haiber S, Nilsson M, et al. Isomer resolution by micelle-assisted diffusion-ordered spectroscopy[J]. Anal Chem, 2009, 81(11): 4 548－4 550.

[22] Chaudhari S R, Suryaprakash N. Diffusion ordered spectroscopy for resolution of double bonded cis, trans-isomers[J]. J Mol Struct, 2012, 1 017: 106－108.

[23] Tormena C F, Evans R, Haiber S, et al. Matrix-assisted diffusion-ordered spectroscopy: application of surfactant solutions to the resolution of isomer spectra[J]. Magn Reson Chem, 2012, 50(6): 458－465.

[24] Pemberton C, Hoffman R E, Aserin A, et al. NMR chromatography using microemulsion systems[J]. Langmuir, 2011, 27(8): 4 497－4 504.

[25] Hoffman R E, Aserin A, Garti N. New insights into the microemulsion-based chromatographic NMR resolution mechanism and its application to fragrance/flavor molecules[J]. J Magn Reson, 2012, 220: 18－25.

[26] Rogerson A K, Aguilar J A, Nilsson M, et al. Simultaneous enhancement of chemical shift dispersion and diffusion resolution in mixture analysis by diffusion-ordered NMR spectroscopy[J]. Chem Commun, 2011, 47(25): 7 063－7 064.

[27] Zhan F P, Yu G Y, Yao B X, et al. Solvent effect in the chromatographic enantioseparation of 1,1-bi-2-naphthol on a polysaccharide-based chiral stationary phase[J]. J Chromatogr A, 2010, 1 217: 4 278－4 284.

[28] Paglia G, D’Apolito O, Tricarico F, et al. Evaluation of mobile phase, ion pairing, and temperature influence on an HILIC-MS/MS method for L-arginine and its dimethylated derivatives detection[J]. J Sep Sci, 2008, 31(3): 2 424－2 429.

[29] Carrara C, Viel S, Delaurent C, et al. Chromatographic NMR in NMR solvents[J]. J Magn Reson, 2008, 194(2): 303－306.

[30] Tormena C F, Evans R, Haiber S, et al. Matrix-assisted diffusion-ordered spectroscopy: mixture resolution by NMR using SDS micelles[J]. Magn Reson Chem, 2010, 48(7): 550－553.

[31] Joyce R E, Day I J. Chromatographic NMR with size exclusion chromatography stationary phases[J]. J Magn Reson, 2012, 220: 1－7.

[32] Huang S H, Wu R, Bai Z W, et al. Evaluation of the separation performance of polyvinylpyrrolidone as a virtual stationary phase for chromatographic NMR[J]. Magn Reson Chem, 2014, 52(9): 486－490.