The methylation reaction in carbohydrate analysis

Journal of Carbohydrate Chemistry

Volumn 15, Issue 8, 1996, Pages 897-923

  Jay, Andrew ^a  

^a INSTITUTE OF FOOD RESEARCH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030516968     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328309608005698     Document Type: Review

References (165)

1. G.O. Aspinall, The Polysaccharides, Vol. 1; Academic Press: New York, 1982, p 35.
2. W.S. York, A.G. Darvill, M. McNeil, T.T. Stevenson and P. Albersheim, Methods Enzymol., 118, 3 (1985).
3. N.C. Carpita and E.M. Shea in Analysis of Carbohydrates by GC and MS; C.J. Biermann and G.D. McGinnis, Eds.; CRC Press: Boca Raton, 1989, p157.
4. R.R. Selvendran and P. Ryden, in Methods in Plant Biochemistry. Vol. 2: Carbohydrates; P.M. Dey and J.B. Harbourne, Eds.; Academic Press: San Diego, 1990, p 549.
5. F-G. Hanisch, Biol. Mass Spec., 23, 309 (1994).
6. I. Ciucanu and C. Luca, Carbohydr. Res., 206, 71 (1990).
7. W.S. York, L.L. Kiefer, P. Albersheim and A.G. Darvill, Carbohydr. Res., 208, 175 (1990).
8. P.W. Needs and R.R. Selvendran, Carbohydr. Res., 245, 1 (1993).
9. P.W. Needs and R.R. Selvendran, Phytochem. Anal., 4, 210 (1993).
10. C.A. MacCormick, J.E. Harris, A.P. Gunning and V.J. Morris, J. Appl. Bacteriol., 74, 196 (1993).
11. K.R. Anamula and P.B. Taylor, Anal. Biochem., 203, 101 (1992).
12. C. Ojinnaka, A.J. Jay, I.J. Colquhoun, G.J. Brownsey, E.R. Morris and V.J. Morris, Int. J. Biol. Macromol., (in press).
13. P. Mischnick, J. Carbohydr. Chem., 10 (4), 711 (1991).
14. I.M. Sims et al., Carbohydr. Res., (in press).
15. G.R. Gray, Methods Enzymol., 138, 26 (1987).
16. T.T. Stevenson and R.H. Furneaux, Carbohydr. Res., 210, 277 (1991).
17. P.J. Harris, R.J. Henry, A.B. Blakeney and B.A. Stone, Carbohydr. Res., 127, 59 (1984).
18. A.B. Blakeney, P.J. Harris, R.J. Henry and B.A. Stone, Carbohydr. Res., 113, 291 (1983).
19. P.W. Needs and R.R. Selvendran, Carbohydr. Res., 254, 229 (1994).
20. D. Rolf, J.A. Bennek and G.R. Gray, Carbohydr. Res., 137, 183 (1985).
21. S.H. Doares, P. Albersheim and A.G. Darvill, Carbohydr. Res., 210, 311 (1991).
22. R. Falshaw and R.H. Furneaux, Carbohydr. Res., 252, 171 (1994).
23. D.P. Sweet, R.H. Shapiro and P. Albersheim, Carbohydr. Res., 40, 217 (1975).
24. H. Björndal, B. Lindberg, Å. Pilotti and S. Svensson, Carbohydr. Res., 15, 339 (1970).
25. L.E. Elvebak II, C. Abbott, S. Wall and G.R. Gray, Carbohydr. Res., 269, 1 (1995).
26. S.G. Zeller and G.R. Gray, Carbohydr. Res., 198, 285 (1990).
27. H.O. Bouveng and B. Lindberg, Adv. Carbohydr. Chem., 15, 53 (1960).
28. T. Purdie and J.C. Irvine, J. Chem. Soc., 83, 1021 (1903).
29. E.L. Hirst and E. Percival, in Methods in Carbohydrate Chemistry, Vol II; R. Whistler and M.L. Wolfrom, Eds; Academic Press: NY & London, 1963, p145.
30. T. Purdie and J.C. Irvine, J. Chem. Soc., 85, 1049 (1904).
31. W.S. Denham and H. Woodhouse, J. Chem. Soc., 103, 1735 (1913).
32. W.N. Haworth, J. Chem. Soc., 107, 8 (1915).
33. W.N. Haworth and E.L. Hirst, J. Chem. Soc., 119, 193 (1921).
34. W.L. Glen, G.S. Myers and G.A. Grant, J. Chem. Soc., 2568 (1951).
35. E.L. Falcover and G.A. Adams, Can. J. Chem., 34, 338 (1956).
36. E. Pascan and S.M. Trister, J. Am. Chem. Soc., 61, 2442 (1939).
37. R. Kuhn, H. Trischmann and I. Löw, Angew. Chem., 67, 32 (1955).
38. N. Kornblum and R.K. Blackwood, J. Am. Chem. Soc., 78, 4037 (1956).
39. R.C. Menzies and C.M. Fear, J. Chem. Soc., 937 (1926).
40. C.C. Barker, E.L. Hirst and J.K.N. Jones, J. Chem. Soc., 783 (1946).
41. H.G. Walker Jr., M. Gee and R.M. McCready, J. Org. Chem., 21, 2100 (1962).
42. L. Schmid and B. Becker, Chem. Ber., 58, 1966 (1925).
43. I.E. Muskat, J. Am. Chem. Soc., 56, 693 (1934).
44. I.E. Muskat, J. Am Chem. Soc., 56, 2449 (1934).
45. R.S. Tipson, in Methods in Carbohydrate Chemistry, Vol II; R. Whistler and M.L. Wolfrom Eds.; Academic Press: NY & London, 1963.
46. K. Freudenberg and W. Rapp, Chem. Ber., 69, 2041 (1936).
47. K. Freudenberg, E. Plankenhorn and H. Boppel, Chem. Ber., 71, 2435 (1938).
48. K. Freudenberg and R.M. Hixon, Chem. Ber., 56, 2119 (1923).
49. J.E. Hodge, S.A. Karjala and G.E. Hilbert, J. Am. Chem. Soc., 73, 3312 (1951).
50. H.S. Isbell, H.L. Frush, B.H. Bruckner, G.N. Kowkabany and G. Wampler, Anal. Chem., 29, 1523 (1957).
51. D.M. Lemal, P.D. Pacht and R.B. Woodward, Tetrahedron, 18, 1275 (1962)
52. S.A. Barker, R.E. Hurst, J. Settine, F.P. Fish and R.L. Settine, Carbohydr. Res., 125, 291 (1984).
53. P. Prehm, Carbohydr. Res., 78, 372 (1980).
54. R.O. Cuoso, L. Ielpi and M.A. Dankert, J. Gen. Microbiol., 133, 2123 (1987).
55. P.-E. Jannson, J. Lindberg, M. Spellman, T. Hofstad and N. Skaug, Carbohydr. Res., 137, 197 (1985).
56. R.L. Taylor and H.E. Conrad, Biochem., 11, 1383 (1972).
57. J.N. BeMiller, Adv. Carbohydr. Chem. Biochem., 22, 25 (1967).
58. J.-B. Kim and N.C. Carpita, Plant Physiol., 98, 646 (1992).
59. I.M. Sims and A. Bacic, Phytochem., 38, 1397 (1995).
60. D.A. Rees, J. Chem. Soc., 5168 (1961).
61. B. Nillson and D. Zopf, Methods Enzymol., 83, 46 (1982)
62. B. Lindberg, J. Lönngren, J.L Thompson and W. Nimmich, Carbohydr. Res., 25, 49 (1972).
63. M.A. O'Neill, R.R Selvendran, V.J. Morris and J. Eagles, Carbohydr. Res., 147, 295 (1986).
64. A.J. Mort and D.T.A Lamport, Anal. Biochem., 82, 289 (1977).
65. C.A. Abeygunawardana, C.A. Bush, S.S. Tjoa, P.V. Fennessey and M.A. McNeil, Carbohydr. Res., 191, 279 (1989).
66. B. Lindberg, J. Lönngren and S. Svensson, Adv. Carbohydr. Chem. Biochem., 31, 185 (1975).
67. Z. Yosizawa, T. Sato and K. Schmid, Biochim. Biophys. Acta, 121, 417 (1966).
68. B. Lindberg and J. Lönngren, Methods Enzymol., 50, 3 (1978).
69. C. Erbing, K. Granath, L. Kenne and B. Lindberg, Carbohydr. Res., 47, c5 (1976).
70. T. Doco, J-M. Wieruszeski and B. Fournet, Carbohydr. Res., 198, 313 (1990).
71. I.J. Goldstein, G.W. Hay, B.A. Lewis and F. Smith, Methods Carbohydr. Chem., 5, 361 (1965).
72. B. Lindberg, J. Lönngren and W. Nimmich, Acta Chem. Scand., 26, 2231 (1972).
73. B. Lindberg, J. Lönngren, U. Rudén and W. Nimmich, Acta Chem. Scand., 27, 3787 (1973).
74. K.C.B. Wilkie and S.-L. Woo, Carbohydr. Res., 4, 399 (1966).
75. R.J. Sturgeon in Methods in Plant Biochemistry. Vol 2: Carbohydrates; P.M. Dey and J.B. Harbourne Eds.; Academic Press: San Diego, 1990, p 5.
76. P. Cairns, V.J. Morris, R.L. Botham and S.G. Ring, J. Cereal Sci., 23, 265 (1996).
77. R.F.H. Dekker and G.N. Richards, Adv. Carbohydr. Chem. Biochem., 32, 277 (1976).
78. F. Guillon, J.-F. Thibault, F.M. Rombouts, A.G.J. Voraga and W. Pilnik, Carbohydr. Res., 190, 97 (1989).
79. H.A. Schols, A.G.J. Voragen and I.J. Colquhoun, Carbohydr. Res., 256, 97 (1994).
80. A.N. de Belder and B. Norrman, Carbohydr. Res., 8, 1 (1968).
81. R. Kuhn and H. Trischmann, Chem. Ber., 96, 284 (1963).
82. K. Wallenfals, G. Bechtler, R. Kuhn, H. Trischmann and H. Egge, Angew. Chem., 75, 1014 (1963).
83. H.C. Srivastava, P.P. Singh, S.N. Harshe and K. Virk, Tetrahedron Lett., 493 (1964).
84. J.E. Corey and M. Chaykovsky, J. Am. Chem. Soc., 84, 866 (1962).
85. S-H. Hakomori, J. Biochem. (Tokyo), 55, 205 (1964).
86. D.M.W Anderson and G.M. Cree, Carbohydr. Res., 2, 162 (1966).
87. P.A. Sandford and H.E. Conrad, Biochem., 5, 1508 (1966).
88. A. Dell, A.J. Reason, K-H. Khoo, M. Panico, R.A. McDowell, and H.R. Morris, Methods Enzymol., 230, 108 (1994).
89. S.B. Levery and S-I. Hakomori, Methods Enzymol., 138, 13 (1987).
90. L.R. Phillip and B.A. Frazer, Carbohydr. Res., 90, 149 (1981).
91. A.B. Blakeney, and B.A. Stone, Carbohydr. Res., 140, 319 (1985).
92. J.P. Parente, P. Cardon, Y. Leroy, J. Montreuil, B. Fornet, and G. Ricart, Carbohydr. Res., 141, 41 (1985).
93. A.L. Kvernheim, Acta Chem. Scand. Ser. B, 41, 150 (1987).
94. H. Rauvala, Carbohydr. Res., 72, 257 (1979).
95. I. Ciucanu and F. Kerek, Carbohydr. Res., 131, 209 (1984).
96. D.P. Sweet, P. Albersheim and R.H. Shapiro, Carbohydr. Res., 40, 199 (1975).
97. R.R. Selvendran and S.E. King, Carbohydr. Res., 195, 87 (1989).
98. T.T. Stevenson, A.G. Darvill and P. Albersheim, Carbohydr. Res., 179, 269 (1988).
99. B. Lindberg, J. Lonngren and J.L. Thompson, Carbohydr. Res., 28, 351 (1973).
100. G.O. Aspinall and K.-G. Rosell, Carbohydr. Res., 57, c23 (1977).
101. R. Somme, Carbohydr. Res., 152, 237 (1986).
102. J.I. Brauman, J.A. Bryson, D.C. Kahl and N.J. Nelson, J. Am. Chem. Soc., 92, 6679 (1970).
103. J. Finne, T. Krusius and H. Rauvala, Carbohydr. Res., 80, 336 (1980).
104. J.H. Exner and E.G. Steiner, J. Am. Chem. Soc., 96, 1782 (1974).
105. P.-E. Jannson, J. Lindberg, K.M.S. Wimalasiri and M.A. Dankert, Carbohydr. Res., 245, 303 (1993).
106. E.G. Steiner and J.M. Gilbert, J. Am. Chem. Soc., 85, 3054 (1963).
107. D.R. Burfield and R.H. Smithers, R.H. J. Org. Chem., 43, 3966 (1978).
108. A.P. Johnson, and A. Pelter, J. Chem. Soc., 520 (1964).
109. C.R. Johnson, and W.G. Phillips, J. Org. Chem., 32, 1926 (1967).
110. U. Zahringer, H. Moll, E.Th. Rietschel, B. Kraska, M. Imoto and S. Kusumoto, Carbohydr. Res., 196, 147 (1990).
111. A. Dell, M.E. Rogers, J.E. Thomas-Oates, T.N. Huckerby, P.N. Sanderson and I.A. Nieduszynski, Carbohydr. Res., 179, 7 (1988).
112. J.A. Lomax, A.H. Gordon and A. Cheeson, Carbohydr. Res., 122, 11 (1983).
113. T. Narui, K. Takahashi, M. Kobayashi and S. Shibata, Carbohydr. Res., 103, 293 (1982).
114. A. Isogai, A. Ishizu, J. Nakauo, S. Eda, and K. Kato, Carbohydr. Res., 138, 99 (1985).
115. A. El-Kafrawy, J. Appl. Polym. Sci., 27, 2435 (1982).
116. J-P. Joseleau, G. Chambat and B. Chumpitazi-Hermoza, Carbohydr. Res., 90, 339 (1981).
117. S.M. Hudson and J.A. Cuculo, J. Macromol. Sci., Rev. Macromol. Chem., 18, 1 (1980).
118. R.J. Ferrier and P.M. Collins, Monosaccharide Chemistry; Penguin: London, 1972.
119. L. Hough and R.S. Theobald, in Methods in Carbohydrate Chemistry, Vol II; R. Whistler and M.L. Wolfrom, Eds; Academic Press: NY & London, 1963 p162.
120. I.O. Mastroni, S.M. Flematti, J.O. Deferrari and E.G. Gros, Carbohydr. Res., 3177 (1966).
121. J. Arnap, L. Kenne, B. Lindberg and J. Lönngren, Carbohydr. Res., 44, c5 (1975).
122. J.M. Berry and L.D. Hall, Carbohydr. Res., 47, 307 (1976).
123. C.R. Wong, L.M. Jackman and R.G. Portman, Tetrahedron Lett., 921 (1974).
124. J.D. Stankowski and S.G. Zeller, Carbohydr. Res., 224, 337 (1992).
125. A.J. Mort, S. Parker and M-S. Kuo, Anal. Biochem., 133, 380 (1983).
126. T.J. Waege, A.G. Darvill, M. McNeil and P. Albersheim, Carbohydr. Res., 123, 281 (1983).
127. A.P. Mathers and M.J. Pro, Anal. Chem., 27, 1662 (1955).
128. B.S. Valent, A.G. Darvill, M. McNeill, B.K. Robertson and P. Albersheim, Carbohydr. Res., 79, 165 (1980).
129. A.G. Darvill, M. McNeill and P. Albersheim, Carbohydr. Res., 86, 309 (1980).
130. M. McNeil, A.G. Darvill, P. Åman, L.K. Franzén and P. Albersheim, Methods Enzymol., 83, 3 (1982)
131. N.C. Carpita and D. Whittern, Carbohydr. Res., 146, 129 (1986).
132. P. Albersheim, D.J. Nevins, P.D. English and A. Karr, Carbohydr. Res., 5, 340 (1967).
133. C.J. Biermann, Adv. Carbohydr. Chem. Biochem., 46, 251 (1989).
134. I. Croon, G. Herrstrom, G. Kull and B. Lindberg, Acta Chem. Scand., 14, 1338 (1960).
135. R.E. Chambers and J.R. Clamp, Biochem. J., 125, 1009 (1971).
136. G.L. Rorrer, M.C. Hawley, S.M. Selke, D.T.A. Lamport and P.M. Dey, in Methods in Plant Biochemistry. Vol. 2: Carbohydrates; P.M. Dey and J.B. Harbourne, Eds.; Academic Press: San Diego, 1990, p 581.
137. P.J. Garregg, B. Lindberg, P. Konradson and I. Kvarnström, Carbohydr. Res., 176, 145 (1988).
138. M.H. Saier Jr. and C.E. Ballou, J. Biol. Chem., 243, 4319 (1968).
139. H.E. Conrad, J.R. Bamburg, J.D. Epley and T.J. Kindt, Biochemistry, 5, 2808 (1975).
140. C.J. Pollock, M.A. Hall and D.P. Roberts, J. Chromatogr., 171, 411 (1979).
141. H. Rauvala, J. Finne, T. Krusius, J. Karkainen and J. Jarnfelt, Adv. Carbohydr. Chem, Biochem., 38, 389 (1981).
142. B. Nillson, Glycoconjugate J., 2, 335 (1985).
143. S. Inoue and M. Miyawaki, Anal. Biochem., 65, 164 (1975).
144. G.A. De Ruiter, H.A. Schols, A.G.J. Voragen and F.M. Rombouts, Anal. Biochem., 207, 176.
145. Yu.A. Knirel, E.V. Vinogradpv amd A.J. Mort, , Adv. Carbohydr. Chem, Biochem., 47, 167 (1989).
146. A.J. Mort, J.P. Utille, G. Torri and A.S. Perlin, Carbohydr. Res., 121, 221 (1983).
147. M.-S. Kuo and A.J. Mort, Carbohydr. Res., 156, 173 (1986).
148. M. Caroff, D.R. Bundle and M.B. Perry, Eur. J. Biochem., 139, 195 (1984).
149. L. Kenne, B. Lindberg, C. Lugowski and S. Svennson, Carbohydr. Res., 151, 349 (1986).
150. D. Rolf and G.R. Gray, J. Am. Chem. Soc., 104, 3539 (1982).
151. J. A. Bennek, D. Rolf and G.R. Gray, J. Carbohydr. Chem., 2, 385 (1983).
152. J.A. Bennek, M.J. Rice and G.R. Gray, Carbohydr. Res., 157, 125 (1986).
153. S.A. Vodonik and G.R. Gray, Carbohydr. Res., 172, 255 (1988).
154. J.-G. Jun and G.R. Gray, Carbohydr. Res., 163, 247 (1987).
155. S.G. Zeller and G.R. Gray, Carbohydr. Res., 211, 309 (1991).
156. J.S. Sherman and G.R. Gray, Carbohydr. Res., 231, 221 (1992).
157. B. Lindberg, Methods Enzymol., 28, 178 (1972).
158. R.J. Redgwell, M.A. O'Neill, R.R. Selvendran and K.J. Parsley, Carbohydr. Res., 153, 97 (1986).
159. R.S. Whiton, P. Lau, S.L. Morgan, J. Gilbart and A. Fox, J. Chromatogr., 347, 109 (1985).
160. K.A. Connors and N.K. Pandit, Anal. Chem., 50, 1542 (1978).
161. G.D. McGinnis, Carbohydr. Res., 108, 284 (1982).
162. H.N. Englyst and J.H. Cummings, Analyst, 103, 937 (1984).
163. M. Abdel-Akher, J.K. Hamilton and F. Smith, J. Am. Chem. Soc., 73, 4691 (1951).
164. P.L. Durette, P. Köll, H. Meyborg and H. Paulson, Chem. Ber., 106, 2333 (1973).
165. A. Coghlan, New Scientist, 10 Sept., 17 (1994).