Metabolite profiling by one- and two-dimensional NMR analysis of complex mixtures

Progress in Nuclear Magnetic Resonance Spectroscopy

Volumn 28, Issue 2, 1996, Pages 161-219

  Fan, Teresa W M ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001413420     PISSN: 00796565     EISSN: None     Source Type: Journal    
DOI: 10.1016/0079-6565(95)01017-3     Document Type: Article

References (141)

1. D.E. Leyden and R.H. Cox, Analytical Applications of NMR, John Wiley & Sons, New York, 1977.
2. F.W. Wehrli and T. Wirthlin, Interpretation of Carbon-13 NMR Spectra, Heyden & Son Ltd., London, 1978.
3. G.C. Levy and R.L. Lichter, Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy, John Wiley & Sons, New York, 1979.
4. D.G. Gadian, Nuclear Magnetic Resonance and Its Applications to Living Systems, Clarendon Press, Oxford, 1982.
5. R.M. Silverstein, G.C. Bassler and T.C. Morrill, Spectrometric Identification of Organic Compounds, John Wiley & Sons, New York, 1991.
6. E. Fukushima and S.B.W. Roeder, Experimental Pulse NMR. A Nuts and Bolts Approach, Addison-Wesley Publishing Company, London, 1981.
7. I. Ando and G.A. Webb, Theory of NMR Parameters, Academic Press, London, 1983.
8. R. Freeman, A Handbook of Nuclear Magnetic Resonance, Longman Scientific & Technical, Harlow, 1988.
9. P.G. Waterman and S. Mole, Analysis of Plant Metabolites, Blackwell Scientific Publications, London, 1994.
10. I. Gutmann and A.W. Wahlefeld, in H.U. Bergmeyer (Ed.), Methods of Enzymatic Analysis, Academic Press, New York, 1974, pp. 1586-1587.
11. W.T. Evanochko, T.T. Sakai, T.C. Ng, N.R. Krishna, H.D. Kim, R.B. Zeidler, V.K. Ghanta, R.W. Brockman, L.M. Schiffer, P.G. Braunschweiger and J.D. Glickson, Biochim. Biophys. Acta, 805 (1984) 104-116.
12. T.W.-M. Fan, R.M. Higashi, A.N. Lane and O. Jardetzky, Biochim. Biophys. Acta, 882 (1986) 154-167.
13. D.C. Crans, M. Mikús and R.W. Marshman, Anal. Biochem., 209 (1993) 85-94.
14. G. Lepage and C.C. Roy, J. Lipid Res., 29 (1988) 227-235.
15. T.W.-M. Fan, A.J. Clifford and R.M. Higashi, J. Lipid Res., 35 (1994) 678-689.
16. K. Ugurbil, R.G. Shulman and T.R. Brown, in R.G. Shulman (Ed.), Biological Applications of Magnetic Resonance, Academic Press, New York, 1979, pp. 537-589.
17. D.L. Rothman, K.L. Behar, H.P. Hetherington and R.G. Shulman, Proc. Natl. Acad. Sci. USA, 81 (1984) 6330-6334.
18. T.W.-M. Fan, T.D. Colmer, A.N. Lane and R.M. Higashi, Anal. Biochem., 214 (1993) 260-271.
19. G.M. Clore and A.M. Gronenborn, Prog. NMR Spectrosc., 23 (1991) 43-92.
20. B.A. Berkowitz, S.D. Wolff and R.S. Balaban, J. Magn. Reson., 79 (1988) 547-553.
21. A. Bax, Ph.D. Thesis, University of Groningen, 1982.
22. C.A.G. Haasnoot, F.J.M. Van De Ven and C.W. Hilbers, J. Magn. Reson., 56 (1984) 343-349.
23. T.W.-M. Fan, R.M. Higashi and A.N. Lane, Arch. Biochem. Biophys., 251 (1986) 674-687.
24. D.G. Neuhaus, G. Wagner, M. Vasak, J.H.R. Kägi and K. Wüthrich, Eur. J. Biochem., 151 (1985) 257-273.
25. M. Rance, O.W. Sørensen, G. Bodenhausen, G. Wagner, R.R. Ernst and K. Wüthrich, Biochem. Biophys. Res. Commun., 117 (1983) 479-485.
26. L. Braunschweiler and R.R. Ernst, J. Magn. Reson., 53 (1983) 521-528.
27. A. Bax and D.G. Davis, J. Magn. Reson., 65 (1985) 355-360.
28. F. Mitsumori and O. Ito, FEBS Lett., 174 (1984) 248-252.
29. G. Navon, R.G. Schulman, T. Yamane, T.R. Eccleshall, K.-B. Lam, J.J. Baronofsky and J. Mamur, Biochemistry, 18 (1979) 4487-4499.
30. T.W.-M. Fan, R.M. Higashi and J.M. Macdonald, Biochim. Biophys. Acta, 1092 (1991) 39-47.
31. W.B. Busa, J.H. Crowe and G.B. Matson, Arch. Biochem. Biophys., 216 (1982) 711-718.
32. E.A. Shoubridge, J.L. Bland and G.K. Radda, Biochim. Biophys. Acta, 805 (1984) 72-78.
33. R.J. Newman, P.J. Bore, L. Chan, D.G. Gadian, P. Styles, D. Taylor and G.K. Radda, Br. Med. J., 284 (1982) 1072-1074.
34. T.W.-M. Fan, A.N. Lane and R.M. Higashi, Arch. Biochem. Biophys., 294 (1992) 314-318.
35. J.K.M. Roberts, D. Wemmer and O. Jardetzky, Plant Physiol., 74 (1984) 632-639.
36. R.B. Lee and R.B. Ratcliffe, J. Exp. Bot., 34 (1983) 1222-1244.
37. D.G. Gadian, in G. Pifat-Mrzljak (Ed.), Supramolecular Structure and Function, Springer-Verlag, Berlin, 1986, pp. 93-103.
38. P.S. Belton and R.G. Ratcliffe, Prog. NMR Spectrosc., 17 (1985) 241-279.
39. J.K.M. Roberts, Annu. Rev. Plant Physiol., 35 (1984) 375-386.
40. C.T. Burt, S.M. Cohen and M. Bárány, Annu. Rev. Biophys. Bioeng., 8 (1979) 1-25.
41. C.T. Burt, T. Glonek and M. Bárány, J. Biol. Chem., 251 (1976) 2584-2591.
42. 31P NMR and Its Applications, Academic Press, New York, 1984.
43. G.A. Morris and L.D. Hall, J. Am. Chem. Soc., 103 (1981) 4703-4711.
44. T.W.-M. Fan and A.N. Lane, Anal. Biochem., 206 (1992) 251-255.
45. M.E. Perlman, D.G. Davis, S.A. Gabel and R.E. London, Biochemistry, 29 (1990) 4318-4325.
46. G.A. Morris and R. Freeman, J. Am. Chem. Soc., 101 (1979) 760.
47. D.M. Doddrell, D.T. Pegg and M.R. Bendall, J. Magn. Reson., 48 (1982) 323.
48. A. Bax, R. Freeman, T.A. Frenkiel and M.H. Levitt, J. Magn. Reson., 43 (1981) 478.
49. F. Martin, Physiol, Veg., 23 (1985) 463-490.
50. J.C. Street, A.-M. Delort, P.S.H. Braddock and K.M. Brindle, Biochem. J., 291 (1993) 485-492.
51. G. Bodenhausen and D.J. Rubin, Chem. Phys. Lett., 69 (1980) 185-189.
52. A. Bax and S.S. Pochapsky, J. Magn. Reson., 99 (1992) 638-643.
53. G. Wider and K. Wüthrich, J. Magn. Reson., 102 (1993) 239-241.
54. M. Piotto, V. Saudek and V. Sklenar, J. Biomolec. Struct., 2 (1992) 661-665.
55. S. Cerdán and J. Seelig, Annu. Rev. Biophys. Biophys. Chem., 19 (1990) 43-67.
56. S.R. Williams and D.G. Gadian, Q.J. Exp. Physiol., 71 (1986) 335-360.
57. M.J. Avison, H.P. Hetherington and R.G. Shulman, Annu. Rev. Biophys. Biophys. Chem., 15 (1986) 377-402.
58. D.L. Rabenstein, J. Biochem. Biophys. Methods, 9 (1984) 277-306.
59. C. Arús, M. Bárány, W.M. Westler and J.L. Markley, J. Magn. Reson., 57 (1984) 519-525.
60. P.F. Agris and I.D. Campbell, Science, 216 (1982) 1325-1327.
61. S. Cerdán, R. Parrilla, J. Santoro and M. Rico, FEBS Lett., 187 (1985) 167-172.
62. D.Y. Sze and O. Jardetzky, Biochim. Biophys. Acta, 1054 (1990) 181-197.
63. I.S. Gribbestad, S.B. Petersen, H.E. Fjøsne, S. Kvinnsland and J. Krane, NMR Biomed., 7 (1994) 181-194.
64. O. Kaplan, P.C. van Zijl and J.S. Cohen, Biochem. Biophys. Res. Commun., 169 (1990) 383-390.
65. C. Arús, M. Bárány, W.M. Westler and J.L. Markley, Clin. Physiol. Biochem., 2 (1984) 49-55.
66. M. Ling and M. Brauer, Physiol. Chem. Phys. Med. NMR, 23 (1991) 229-238.
67. C.T. Burt and H.J. Ribolow, Biochem. Med., 31 (1984) 21-30.
68. J.K. Nicholson and I.D. Wilson, Progr. NMR Spectrosc., 21 (1989) 449-501.
69. R.L. Baxter, N.E. Mackenzie and A.I. Scott, in L.J. Berliner and J. Reuben (Eds.), Biological Magnetic Resonance, Vol. 5, Plenum Press, New York, 1983, p. 1-20.
70. R.E. London, Progr. NMR Spectrosc., 20 (1988) 337-383.
71. C.T.W. Moonen, R.J. Dimand and K.L. Cox, Magn. Reson. Med., 6 (1988) 140-157.
72. S.M. Cohen, Biochemistry, 26 (1987) 563-572.
73. F. Martin, D. Canet and J.P. Marchal, Plant Physiol., 77 (1985) 499-502.
74. M. Bárány, C. Arús and Y.-C. Chang, Magn. Reson. Med., 2 (1985) 289-295.
75. K.J. Neurohr, E.J. Barrett and R.G. Shulman, Proc. Natl. Acad. Sci. USA, 80 (1983) 1603-1607.
76. R.S. Norton, Comp. Biochem. Physiol., 63B, (1979) 67-72.
77. T.W.-M. Fan, A.N. Lane and R.M. Higashi, in M.B. Jackson and C.R. Black (Eds.), Interacting Stresses on Plants in a Changing Climate, NATO ASI Series, Vol. 116, Springer-Verlag, Berlin, 1993, pp. 333-352.
78. S. Cerdán, B. Künnecke and J. Seelig, J. Biol. Chem., 265 (1990) 12916-12926.
79. R.S. Badar-Goffer, O. Ben-Yoseph, H.S. Bachelard and P.G. Morris, Biochem. J., 282 (1992) 225-230.
80. J.R. Brainard, R.S. Downey, D.M. Bier and R.E. London, Anal. Biochem., 176 (1989) 307-312.
81. R.E. London and T.E. Walker, Biosci. Rep., 5 (1985) 509-515.
82. J.M. Chalovich, C.T. Burt, S.M. Cohen, T. Glonek and M. Bárány, Arch. Biochem. Biophys., 182 (1977) 683-689.
83. T. Glonek, S.J. Kopp, E. Kot, J.W. Pettegrew, W.H. Harrison and M.M. Cohen, J. Neurochem., 39 (1982) 1210-1219.
84. P.-M.L. Robitaille, K.G. Mumford and G.G. Brown, Biochem. Cell. Biol., 65 (1987) 474-485.
85. K.D. Barrow, D.D. Jamieson and R.S. Norton, Eur. J. Biochem., 103 (1980) 289-297.
86. R.A.J. Challiss, D.J. Hayes, R.F.H. Petty and G.K. Radda, Biochem. J., 236 (1986) 461-467.
87. J.L. Galazzo, J.V. Shanks and J.E. Bailey, Biotechnol. Bioeng., 35 (1990) 1164-1168.
88. R.R. Moore, C.T. Burt and M.F. Roberts, Biochim. Biophys. Acta, 846 (1985) 394-397.
89. K. Kanamori, T.L. Legerton, R.L. Weiss and J.D. Roberts, J. Biol. Chem., 257 (1982) 14168-14172.
90. N. Haran, Z.E. Kahana and A. Lapidot, J. Biol. Chem., 258 (1983) 12929-12933.
91. F. Martin, FEBS Lett., 182 (1985) 350-354.
92. F. Martin, G.R. Stewart, I. Genetet and F. Le Tacon, New Phytol., 102 (1986) 85-94.
93. V.S. Narayan and P.M. Nair, Phytochemistry, 29 (1990) 367-375.
94. G.E. Nilsson and P.L. Lutz, Comp. Biochem. Physiol., 105C (1993) 329-336.
95. K. Wüthrich, NMR in Biological Research: Peptides and Proteins, North-Holland Publishing Co., New York, 1976.
96. G.D. Fasman (Ed.), CRC Handbook of Biochemistry and Molecular Biology, Proteins, 3rd edn., Vol. I, CRC Press, Inc., Cleveland, 1975, p. 112.
97. G. Blunden and S.M. Gordon, Progr. Phycological Res., 4 (1986) 39-80.
98. C.H. Han and L.O. Sillerud, Magn. Reson. Med., 3 (1986) 626-633.
99. G.D. Fasman (Ed.), CRC Handbook of Biochemistry and Molecular Biology. Physical and Chemical Data, 3rd edn., Vol. I, CRC Press, Inc., Cleveland, 1975, p. 309.
100. A.S. Perlin, B. Casu and H.J. Koch, Can. J. Chem., 48 (1970) 2596-2606.
101. D.E. Dorman and J.D. Roberts, J. Am. Chem. Soc., 92 (1970) 1355-1361.
102. P.E. Pfeffer, K.M. Valentine and F.W. Parrish, J. Am. Chem. Soc., 101 (1979) 1265-1274.
103. W. Voelter, E. Breitmaier, E.B. Rathbone and A.M. Stephen, Tetrahedron, 29 (1973) 3845-3848.
104. D.J. Wilbur, C. Williams and A. Allerhand, J. Am. Chem. Soc., 99 (1977) 5450-5452.
105. I.E. Walker, R.E. London, T.W. Whaley, R. Barker and N.A. Matwiyoff, J. Am. Chem. Soc., 98 (1976) 5807-5813.
106. P.A.J. Gorin and M. Mazurek, Can. J. Chem., 53 (1975) 1212-1223.
107. R. Kasai, M. Okihara, J. Asakawa, K. Mizutani and O. Tanaka, Tetrahedron, 35 (1979) 1427-1432.
108. W. Voelter and E. Breitmaier, Org. Magn. Reson., 5 (1973) 311-319.
109. K. Mitzutani, R. Kasai and O. Tanaka, Carbohydr. Res., 87 (1980) 19-26.
110. K. Bock and C. Pedersen, unpublished results.
111. E. Breitmaier and U. Hollstein, Org. Magn. Reson., 8 (1976) 573-575.
112. K. Bock and C. Pedersen, Acta Chem. Scand., Ser. B, 29 (1975) 258-264.
113. J.-P. Utille and P.J.A. Vottero, Carbohydr. Res., 85 (1980) 289-297.
114. D. Doddrell and A. Allerhand, J. Am. Chem. Soc., 93 (1971) 2779-2781.
115. L. Que and G.R. Gray, Biochemistry, 13 (1974) 146-153.
116. S.J. Angyal and G.S. Bethell, Aust. J. Chem., 29 (1976) 1249-1265.
117. W. Funcke, C. von Sonntag and C. Triantaphylides, Carbohydr. Res., 75 (1979) 305-309.
118. V.H. Kollman, J.L. Hanners, R.E. London, E.G. Adame and T.E. Walker, Carbohydr. Res., 73 (1979) 193-202.
119. T.E. Walker, R.E. London, T.W. Whaley, R. Barker and N.A. Matwiyoff, J. Am. Chem. Soc., 98 (1976) 5807-5813.
120. S.J. Perkins, L.N. Johnson and D.C. Phillips, Carbohydr. Res., 59 (1977) 19.
121. J.B. Stothers, Carbon-13 NMR Spectroscopy, Academic Press, New York, 1972.
122. L.F. Johnson and W.C. Jankowski, Carbon-13 NMR Spectra. A Collection of Assigned, Coded, and Indexed Spectra, John Wiley & Sons, New York, 1972, p. 443.
123. G. Blunden, S.M. Gordon, T.A. Crabb, O.G. Roch, M.G. Rowand and B. Wood, Magn. Reson. Chem., 24 (1986) 965-971.
124. D.B. Davies and S.S. Danyluk, Biochemistry, 13 (1974) 4417-4434.
125. O. Jardetzky and G.C.K. Roberts, NMR in Molecular Biology, Academic Press, New York, 1981, p. 188.
126. C.J. Pouchert and J.R. Campbell, The Aldrich Library of NMR Spectra, Vol. 9, Aldrich Chemical Co., 1974, pp. 85-86.
127. J.L. Alderfer, R.E. Loomis and T. Zielinski, Biochemistry, 12 (1982) 2738.
128. D.J. Ashworth, D.O. Adams, B.Y. Giang, M.T.-H. Cheng and R.Y. Lee, Anal. Chem., 57 (1985) 710-715.
129. W.T. Evanochko, R.C. Reeves, T.T. Sakai, R.C. Canby and G.M. Pohost, Magn. Reson. Med., 5 (1987) 23-31.
130. J. Alonso, C. Arús, W.M. Westler and J.L. Markley, Magn. Reson. Med., 11 (1989) 316-330.
131. J.R. Bales, D.P. Higham, I. Howe, J.K. Nicholson and P.J. Sadler, Clin. Chem., 30 (1984) 426-432.
132. B. Birdsall and J. Feeney, J. Chem. Soc., Perkin II, (1972) 1643-1649.
133. C.J. Unkefer and R.E. London, J. Biol. Chem., 259 (1984) 2311-2320.
134. B. Birdsall, Ph.D. Thesis, Cambridge University, 1972.
135. Solvent data sheet published by Merck Sharpe & Dohme, Inc.
136. D.G. Gadian, in R.G. Shulman (Ed.), Biological Applications of Magnetic Resonance, Academic Press, New York, 1979, p. 463.
137. C.T. Burt, T. Glonek and M. Bárány, Biochemistry, 15 (1976) 4850-4853.
138. G. Navon, S. Ogawa, R.G. Shulman and T. Yamane, Proc. Natl. Acad. Sci. USA, 74 (1977) 87.
139. K.D. Barrow, J.G. Collins, R.S. Norton, P.L. Rogers and G.M. Smith, J. Biol. Chem., 259 (1984) 5711.
140. 15N-NMR Spectroscopy, Springer-Verlag, Berlin, 1981, pp. 112-113.
141. R.E. London, T.E. Walker, T.W. Whaley and N.A. Matwiyoff, Org. Magn. Reson., 9 (1977) 598-600.