NMR tools for biotechnology

Current Opinion in Biotechnology

Volumn 10, Issue 1, 1999, Pages 34-41

  Keifer, Paul A ^a  

^a Varian Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOTECHNOLOGY; CHROMATOGRAPHY; DRUG BINDING; FLOW INJECTION ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; LABORATORY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTEIN ANALYSIS; REVIEW; SAMPLE;

EID: 0032943579     PISSN: 09581669     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0958-1669(99)80007-X     Document Type: Article

References (86)

1. 1H NMR in solid-phase organic synthesis. J Org Chem. 59:1994;7955-7956.
2. Keifer PA, Baltusis L, Rice DM, Tymiak AA, Shoolery JN A comparison of NMR spectra obtained for solid-phase-synthesis resins using conventional high-resolution, magic-angle-spinning, and high-resolution magic-angle-spinning probes. J Magn Resonance A. 119:1996;65-75.
3. 1H NMR spectra of solid-phase-synthesis resins. J Org Chem. 61:1996;1558-1559.
4. Gallop MA, Fitch WL New methods for analyzing compounds on polymeric supports. Curr Opin Chem Biol. 1:1997;94-100.
5. Keifer PA High-resolution NMR techniques for solid-phase synthesis and combinatorial chemistry. Drug Discov Today. 2:1997;468-478.
6. Keifer PA New methods for obtaining high-resolution NMR spectra of solid-phase synthesis resins, natural products, and solution-state combinatorial chemistry libraries. Drugs of the Future. 23:1998;301-317. This is not only a critical review, but is also the most exhaustive review known in this field; with 116 references. Of equal importance, it introduces FIA and DI NMR. It is the most comprehensive of the two initial publications that describe FIA-NMR and DI-NMR.
7. Shapiro MJ, Chin J, Marti RE, Jarosinski MA Enhanced resolution in MAS NMR for combinatorial chemistry. Tetrahedron Lett. 38:1997;1333-1336.
8. Chin J, Fell B, Pochapsky S, Shapiro MJ, Wareing JR 2D SECSY NMR for combinatorial chemistry. High resolution MAS spectra for resin-bound molecules. J Org Chem. 63:1998;1309-1311.
9. Meissner A, Bloch P, Humpfer E, Spraul M, Sørensen OW Reduction of inhomogeneous line broadening in two-dimensional high-resolution MAS NMR spectra of molecules attached to swelled resins in solid-phase synthesis. J Am Chem Soc. 119:1997;1787-1788.
10. Dhalluin C, Boutillon C, Tartar A, Lippens G Magic angle spinning nuclear magnetic resonance in solid-phase peptide synthesis. JAm Chem Soc. 119:1997;10494-10500.
11. Jelinek R, Valente AP, Valentine KG, Opella SJ Two-dimensional NMR spectroscopy of peptides on beads. J Magn Resonance. 125:1997;185-187.
12. Chin J, Fell B, Shapiro MJ, Tomesch J, Wareing JR, Bray AM Magic angle spinning NMR for reaction monitoring and structure determination of molecules attached to multipin crowns. J Org Chem. 62:1997;538-539.
13. Maas WE, Laukien FH, Cory DG Gradient, high resolution, magic angle sample spinning NMR. J Am Chem Soc. 118:1996;13085-13086.
14. Rinaldi PL, Keifer P The utility of pulsed-field-gradient HMBC for organic structure determination. J Magn Resonance. 108:1994;259-262.
15. Parella T Pulsed field gradients: a new tool for routine NMR. Magn Resonance Chem. 36:1998;467-495.
16. 15N NMR. Tetrahedron Lett. 38:1997;8643-8646.
17. Rodebaugh R, Joshi S, Fraser-Reid B, Geysen HM Polymer-supported oligosaccharides via n-pentenyl glycosides: methodology for a carbohydrate library. J Org Chem. 62:1997;5660-5661.
18. Gordon EM, Gallop MA, Patel DV Strategy and tactics in combinatorial organic synthesis. Applications to drug discovery. Accounts Chem Res. 29:1996;144-154.
19. Gordeev MF, Gordon EM, Patel DV Solid-phase synthesis of β-sultams. J Org Chem. 62:1997;8177-8181.
20. Hamper BC, Kolodziej SA, Scates AM, Smith RG, Cortez E Solid phase synthesis of β-peptoids: N-substituted β-aminopropionic acid oligomers. J Org Chem. 63:1998;708-718.
21. Cheng LL, Ma MJ, Becerra L, Ptak T, Tracey I, Lackner A, Gonzalez RG Quantitative neuropathology by high resolution magic angle spinning proton magnetic resonance spectroscopy. Proc Natl Acad Sci USA. 94:1997;6408-6413.
22. Millis KK, Maas WE, Cory DG, Singer S Gradient, high-resolution, magic-angle spinning nuclear magnetic resonance spectroscopy of human adipocyte tissue. Magn Reson Med. 38:1997;399-403.
23. 1H nuclear magnetic resonance spectroscopy. J Pharm Biomed Anal. 17:1998;125-132. This paper gives a nice illustration of where HR-MAS will undoubtedly be going in the future. Although the data were not obtained rapidly, and so do not constitute a demonstration of a high-throughput clinical technique, they do show the significant potential of using this technique for research purposes.
24. 2O was determined using 2D-NMR methods.
25. Manzi AE, Keifer PA New frontiers in nuclear magnetic resonance spectroscopy. Use of a NanoNMR probe for the analysis of microgram quantities of complex carbohydrates. Townsend RR, Hotchkiss AT Jr. Techniques in Glycobiology. 1997;1-16 Marcel Dekker, Inc, New York.
26. Chauret DC, Durst T, Arnason JT, Sanchez-Vindas P, Roman LS, Poveda L, Keifer PA Novel steroids from Trichilia hirta as identified by Nanoprobe INADEQUATE 2D-NMR spectroscopy. Tetrahedron Lett. 37:1996;7875-7878.
27. Shoolery JN Small coils for NMR microsamples. Top Carbon-13 NMR Spectrosc. 3:1979;28-38.
28. Martin GE, Crouch RC, Zens AP Gradient submicro inverse detection: rapid acquisition of inverse-detected heteronuclear chemical shift correlation data on submicromole quantities of material. Magn Reson Chem. 36:1998;551-557.
29. Webb AG Radiofrequency microcoils in magnetic resonance. Prog Nucl Magn Reson Spectros. 31:1997;1-42. A review with 183 references on the development of various kinds of microcoils for solution-state NMR.
30. Korhammer SA, Bernruether A Hyphenation of high-performance liquid chromatography (HPLC) and other chromatographic techniques (SFC, GPC, GC, CE) with nuclear magnetic resoance (NMR): a review. Fresenius J Anal Chem. 354:1996;131-135.
31. Lindon JC, Nicholson JK, Wilson ID Direct coupling of chromatographic separations to NMR spectroscopy. Prog Nucl Magn Reson Spectros. 29:1996;1-49.
32. Lindon JC, Nicholson JK, Wilson ID The development and application of coupled HPLC-NMR spectroscopy. Adv Chromatogr (NY). 36:1996;315-382.
33. Watanabe N, Niki E Direct-coupling of FT-NMR to high performance liquid chromatography. Proc Jpn Acad Ser B. 54:1978;194-199.
34. Sidelmann UG, Hansen SH, Gavaghan C, Carless HAJ, Farrant RD, Lindon JC, Wilson ID, Nicholson JK Measurement of internal acyl migration reaction kinetics using directly coupled HPLC-NMR: application for the positional isomers of synthetic (2-fluorobenzoyl)-D-glucopyranuronic acid. Anal Chem. 68:1996;2564-2572.
35. 1H NMR to environmental samples: analysis of groundwater near former ammunition plants. Anal Chem. 69:1997;3832-3837.
36. 1H NMR spectroscopy for the structural determination of retinyl acetate dimers: 2D NMR spectroscopy in the nanoliter scale. Anal Chem. 69:1997;1421-1425.
37. Strohschein S, Pursch M, Handel H, Albert K Structure elucidation of β-carotene isomers by HPLC-NMR coupling using a C30-bound phase. Fresenius J Anal Chem. 357:1997;498-502.
38. Sidelmann UG, Lenz EM, Spraul M, Hoffmann M, Troke J, Sanderson PN, Lindon JC, Wilson ID, Nicholson JK 750 MHz HPLC-NMR spectroscopic studies on the separation and characterization of the positional isomers of the glucuronides of 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-acetic acid. Anal Chem. 68:1996;106-110.
39. Ute K, Nimi R, Hongo S, Hatada K Direct determination of molecular distribution by size exclusion chromatography with 750MHz 1H NMR detection (on-line SEC-NMR). Polym J. 30:1998;439-443.
40. Corcoran O, Spraul M, Hofmann M, Ismail IM, Lindon JC, Nicholson JK 750 MHz HPLC-NMR spectroscopic identification of rat microsomal metabolites of phenoxypyridines. J Pharm Biomed Anal. 16:1997;481-489.
41. Sidelmann UG, Braumann U, Hofmann M, Spraul M, Lindon JC, Nicholson JK, Hansen SH Directly coupled 800 MHz HPLC-NMR spectroscopy of urine and its application in the identification of the major phase II metabolites of tolfenamic acid. Anal Chem. 69:1997;607-612.
42. Anderson WA, Brey WW, Brooke AL, Cole B, Delin KA, Fuks LF, Hill HDW, Johanson ME, Kotsubo VY, Nast Ret al. High-sensitivity NMR spectroscopy probe using superconductive coils. Bull Magn Reson. 17:1995;98-102.
43. 19F-NMR kinetic data.
44. Wu N, Webb A, Peck TL, Sweedler JV Online NMR detection of amino acids and peptides in microbore LC. Anal Chem. 67:1995;3101-3107.
45. Albert K, Schlotterbeck G, Tseng L-H, Braumann U Application of online capillary high-performance liquid chromatography-nuclear magnetic resonance spectrometry coupling for the analysis of vitamin A derivatives. J Chromatogr. 750:1996;303-309.
46. 1H NMR spectroscopy in the nanoliter scale. Anal Chem. 68:1996;1110-1115.
47. Smallcombe SH, Patt SL, Keifer PA WET solvent suppression and its applications to LC NMR and high-resolution NMR spectroscopy. J Magn Reson A. 117:1995;295-303.
48. Pullen FS, Swanson AG, Newman MJ, Richards DS 'Online' liquid chromatography/nuclear magnetic resonance mass spectrometry - a powerful spectroscopic tool for the analysis of mixtures of pharmaceutical interest. Rapid Commun Mass Spectrom. 9:1995;1003-1006.
49. 1H-NMR. Macromolecules. 29:1996;6556-6559.
50. Holt RM, Newman MJ, Pullen FS, Richards DS, Swanson AG High-performance liquid chromatography/NMR spectrometry/mass spectrometry: further advances in hyphenated technology. J Mass Spectrom. 32:1997;64-70. This article is an update on LC-NMR-MS developments from the group that first developed the technique. The incorporation of an electrospray MS interface is described. The power and applicability of this technique to the analysis of a combinatorial-chemistry library are demonstrated.
51. Hostettmann K, Wolfender JL, Rodriguez S Rapid detection and subsequent isolation of bioactive constituents of crude plant extracts. Planta Med. 63:1997;2-10.
52. Wolfender J-L, Rodriguez S, Hostettmann K, Hiller W Liquid chromatography/ultra violet/mass spectrometric and liquid chromatography/nuclear magnetic resonance spectroscopic analysis of crude extracts of Gentianaceae species. Phytochem Anal. 8:1997;97-104.
53. 1H NMR. Polymer. 39:1998;1515-1523.
54. Wolfender J-L, Rodriguez S, Hostettmann K Liquid chromatography coupled to mass spectrometry and nuclear magnetic resonance spectroscopy for the screening of plant constituents. JChromatogr. 794:1998;299-316. The paper provides a nice example of the utility of LC-NMR, especially as a technique which is complimentary to other available analytical tools, such as LC-UV and LC-MS. Crude plant extracts were analyzed directly to identify bioactive metabolites using both on-flow and stopped-flow LC-NMR.
55. Ehlhardt WJ, Woodland JM, Baughman TM, Vandenbranden M, Wrighton SA, Kroin JS, Norman BH, Maple SR Liquid chromatography/nuclear magnetic resonance spectroscopy and liquid chromatography/mass spectrometry identification of novel metabolites of the multidrug resistance modulator LY335979 in rat bile and human liver microsomal incubations. Drug Metab Dispos. 26:1998;42-51.
56. Shockcor JP, Unger SH, Wilson ID, Foxall PJD, Nicholson JK, Lindon JC Combined HPLC, NMR spectroscopy, and ion-trap mass spectrometry with application to the detection and characterization of xenobiotic and endogenous metabolites in human urine. Anal Chem. 68:1996;4431-4435.
57. Griffiths L, Horton R Optimization of LC-NMR. III. Increased signal-to-noise ratio through column trapping. Magn Reson Chem. 36:1998;104-109.
58. 1H NMR for the analysis of mixtures of isomeric ester glucuronide conjugates of trifluoromethy-lbenzoic acids. J Chromatogr. 728:1996;377-385.
59. 2H detection with application to the metabolism of N-dimethylformamide-d7. JPharm Biomed Anal. 16:1997;1-5.
60. Foxall PJD, Lenz EM, Lindon JC, Neild GH, Wilson ID, Nicholson JK Nuclear magnetic resonance and high-performance liquid chromatography-nuclear magnetic resonance studies on the toxicity and metabolism of ifosfamide. Ther Drug Monit. 18:1996;498-505.
61. Van Gorkom LCM, Hancewicz TM Analysis of DOSY and GPC-NMR experiments on polymers by multivariate curve resolution. JMagn Reson. 130:1998;125-130.
62. 1H NMR coupling. J Chromatogr. 761:1997;336-340.
63. Spraul M, Braumann U, Renault J-H, Thepenier P, Nuzillard J-M Nuclear magnetic resonance monitoring of centrifugal partition chromatography in pH-zone-refining mode. J Chromatogr. 766:1997;255-260.
64. Mistry N, Ismail IM, Smith MS, Nicholson JK, Lindon JC Characterization of impurities in bulk drug batches of fluticasone propionate using directly coupled HPLC-NMR spectroscopy and HPLC-MS. J Pharm Biomed Anal. 16:1997;697-705.
65. Shockcor JP, Wurm RM, Frick LW, Sanderson PN, Farrant RD, Sweatman BC, Lindon JC HPLC-NMR identification of the human urinary metabolites of (-)-cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine, a nucleoside analog active against human immunodeficiency virus (HIV). Xenobiotica. 26:1996;189-199.
66. Chin J, Fell JB, Jarosinski M, Shapiro MJ, Wareing JR HPLC/NMR in combinatorial chemistry. J Org Chem. 63:1998;386-390.
67. Scarfe GB, Wilson ID, Spraul M, Hofmann M, Braumann U, Lindon JC, Nicholson JK Application of directly coupled high-performance liquid chromatography-nuclear magnetic resonance-mass spectrometry to the detection and characterization of the metabolites of 2-bromo-4-trifluoromethylaniline in rat urine. Anal Commun. 34:1997;37-39.
68. Clayton E, Taylor S, Wright B, Wilson ID The application of high performance liquid chromatography, coupled to nuclear magnetic resonance spectroscopy and mass spectrometry (HPLC-NMR-MS), to the characterization of ibuprofen metabolites from human urine. Chromatographia. 47:1998;264-270.
69. Hostettmann K, Potterat O, Wolfender JL The potential of higher plants as a source of new drugs. Chimia. 52:1998;10-17.
70. Vogler B, Klaiber I, Roos G, Walter CU, Hiller W, Sandor P, Kraus W Combination of LC-MS and LC-NMR as a tool for the structure determination of natural products. J Nat Prod. 61:1998;175-178.
71. Strohschein S, Schlotterbeck G, Richter J, Pursch M, Tseng L-H, Haendel H, Albert K Comparison of the separation of cis/trans isomers of tretinoin with different stationary phases by liquid chromatography-nuclear magnetic resonance coupling. JChromatogr. 765:1997;207-214. This paper is a good example of the unique utility of NMR as a detector for liquid chromatography. The unstable isomers of retinoic acid, which are essentially indistinguishable by mass spectroscopy and UV, and which readily interconvert, are separated and studied with liquid chromatography-NMR.
72. 1H-NMR coupling for the analysis of fatty alcohol ethoxylates. Polym Bull (Berlin). 38:1997;673-679.
73. Godejohann M, Preiss A, Muegge C Quantitative measurements in continuous-flow HPLC/NMR. Anal Chem. 70:1998;590-595.
74. Burton KI, Everett JR, Newman MJ, Pullen FS, Richards DS, Swanson AG Online liquid chromatography coupled with high field NMR and mass spectrometry (LC-NMR-MS): a new technique for drug metabolite structure elucidation. J Pharm Biomed Anal. 15:1997;1903-1912.
75. Haw JF, Glass TE, Dorn HC Continuous flow high field nuclear magnetic resonance detector for liquid chromatographic analysis of fuel samples. Anal Chem. 53:1981;2327-2332.
76. Ruzicka J, Hansen EH Flow injection analyses. Part 1. A new concept of fast continuous flow analysis. Anal Chim Acta. 78:1975;145-157.
77. Sykes BD, Grimaldi JJ Stopped-flow nuclear magnetic resonance spectroscopy. Methods Enzymol. 49:1978;295-321.
78. 1H NMR spectral data is a complex problem. This paper investigates several techniques which show promise for spectral simplification by removing the extraneous coupling-constant information. These methods might allow high-throughput NMR techniques to generate data which can be rapidly and reliably analyzed by computer.
79. Morris KF, Johnson CS Jr. Resolution of discrete and continuous molecular size distributions by means of diffusion-ordered 2D NMR spectroscopy. J Am Chem Soc. 115:1993;4291-4299.
80. Barjat H, Morris GA, Smart S, Swanson AG, Williams SCR High-resolution diffusion-ordered 2D spectroscopy (HR-DOSY) - a new tool for the analysis of complex mixtures. J Magn Resonance B. 108:1995;170-172.
81. 1H NMR spectroscopy of biological fluids. Anal Chem. 68:1996;3370-3376.
82. Hajduk PJ, Olejniczak ET, Fesik SW One-dimensional relaxation- and diffusion-edited NMR methods for screening compounds that bind to macromolecules. J Am Chem Soc. 119:1997;12257-12261. This is a nice overview of the techniques that will probably prove to be very useful tools for mixture analysis in the future. Several groups are reporting similar developments during this timeframe, which is further evidence of their significant potential.
83. Lin M, Shapiro MJ, Wareing JR Screening mixtures by affinity NMR. J Org Chem. 62:1997;8930-8931.
84. Gonnella N, Lin M, Shapiro MJ, Wareing JR, Zhang X Isotope-filtered affinity NMR. J Magn Resonance. 131:1998;336-338.
85. Hajduk PJ, Meadows RP, Fesik SW Discovering high-affinity ligands for proteins. Science. 278:1997;497-499. This paper, and the references cited therein, describe the use of NMR as a tool to directly evaluate ligand binding (SAR by NMR). The use of flow NMR to implement high-throughput versions of this technique is becoming of interest to many other groups.
86. Ross A, Salzmann M, Senn H Fast-HMQC using Ernst angle pulses: an efficient tool for screening of ligand binding to target proteins. J Biomol NMR. 10:1997;389-396.