Phosphopeptides - Chemical synthesis, analysis, outlook and limitations

Current Organic Chemistry

Volumn 11, Issue 5, 2007, Pages 409-426

  Toth G K ^a   Kele, Z ^a   Varadi G ^a  

^a UNIVERSITY OF SZEGED   (Hungary)

Author keywords

Collision induced dissociation(CID); Phosphate protecting groups; Phosphorylation; PSD MALDI; Tert butyldimethylsilyl

Indexed keywords

BIOSYNTHESIS; PEPTIDES; SIGNAL TRANSDUCTION;

CELL REGULATION; CHEMICAL LIMITATION; COLLISION INDUCED DISSOCIATION; PHOSPHATE PROTECTING GROUP; PHOSPHOPEPTIDES; PROTECTING GROUP; PROTEIN PHOSPHORYLATION; PSD/MALDI; SYNTHESIS ANALYSIS; TERT-BUTYLDIMETHYLSILYL;

PHOSPHORYLATION;

PHOSPHATE; PHOSPHOPEPTIDE; PHOSPHOSERINE; PHOSPHOTHREONINE; PHOSPHOTYROSINE;

DEPHOSPHORYLATION; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; PHOSPHORYLATION; PROTEIN ISOLATION; PROTEIN PHOSPHORYLATION; REVIEW; SIGNAL TRANSDUCTION;

EID: 33847763558     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527207780059295     Document Type: Review

References (130)

1. Ferrel, R.E.; Olcott, H.S.; Fraenkel-Conrat, H. J. Am. Chem. Soc., 1948, 70, 2101.
2. Atherton, F.R.; Openshaw, H.T.; Todd, A.R. J. Chem. Soc., 1945, 660.
3. McMurray, J.S.; Coleman, D.R., IV; Wang, W.; Campbell, M.L. Biopolymers, 2001, 60, 3.
4. Alewood, P.F.; Johns, R.B.; Valerio, R.M.; Kemp, B.E. Synthesis, 1983, 1, 30.
5. Ottinger, E.A.; Shekels, L.L.; Bernlohr, D.A.; Barany, G. Biochemistry, 1993, 32, 4354.
6. Conrad, S.F.; Kaumaya, P.T.P. In Peptides: Chemistry, Structure and Biology; Kaumaya and Hodges, Eds,; Mayflower Scientific Ltd: Kingswinford, 1996; pp. 446-447.
7. Ottinger, E.A.; Xu, Q.; Barany, G. In Innovation and Perspectives in Solid Phase Synthesis & Combinatorial Libraries: Peptides, Proteins and Nucleic Acids - Small Molecule Organic Chemical Diversity; Epton, Ed.; Mayflower Scientific: Birmingham, 1996; pp. 495-498.
8. Garcia-Echeverria, C. Lett. Pept. Sci., 1996, 9, 223.
9. Valerio, R.M.; Alewood, P.F.; Johns, R.B.; Kemp, B.E. Tetrahedron Lett., 1984, 25, 2609.
10. Valerio, R.M.; Alewood, P.F.; Johns, R.B.; Kemp, B.E. Int. J. Pept. Protein Res., 1989, 33, 428.
11. Valerio, R.M.; Perich, J.W.; Kitas, E.A.; Alewood, P.F.; Johns, R.B. Aust. J. Chem., 1989, 42, 1519.
12. Gibson, B.W.; Falick, A.M.; Burlingame, A.L.; Nadasdi, L.; Nguyen, A.C.; Kenyon, G.L. J. Am. Chem. Soc., 1987, 109, 5343.
13. Wade, J.D.; Perich, J.W.; McLeish, M.J.; Otvos, L.; Tregear, G.W. Lett. Pept. Sci., 1995, 2, 71.
14. Kitas, E.A.; Johns, R.B.; May, C.N.; Tregear, G.W.; Wade, J.D. Pept. Res., 1993, 6, 205.
15. Bannwarth, W.; Kitas, E.A. Helv. Chim. Acta, 1992, 75, 707.
16. Kitas, E.A.; Perich, J.W.; Tregear, G.W.; Johns, R.B. J. Org. Chem., 1990, 55, 4181.
17. Kitas, E.A.; Perich, J.W.; Wade, J.D.; Johns, R.B.; Tregear, G.W. Tetrahedron Lett., 1989, 30, 6229.
18. Otaka, A.; Miyoshi, K.; Kaneko, M.; Tamamura, H.; Fujii, N.; Nomizu, M.; Burke, T.R.; Roller, P.P. J. Org. Chem., 1995, 60, 3967.
19. Toth, G.K.; Varadi, G.; Janaky, T.; Penke, B.; Mak, M.; Lang, E.; Otvos, L.; Hegedus, Z.; Monostori, E. In Peptides 1994 Proc. of the 23th European Peptide Symposium; Maia, Ed.; Escom Science Publ.; 1995; pp. 743-744.
20. Toth, G.K.; Laczko, I.; Hegedus, Z.; Vass, E.; Hollosi, M.; Janaky, T.; Varadi, G.; Penke, B.; Monostori, E. In Peptides in Immunology; Schneider, Ed.; John Wiley & Sons, Ltd; 1996; pp. 223-230.
21. Valerio, R.M.; Bray, A.M.; Maeji, N.J.; Morgan, P.O.; Perich, J.W. Lett. Pept. Sci., 1995, 2, 33.
22. Wakamiya, T.; Togashi, R.; Nishida, T.; Saruta, K.; Yasuoka, J.; Kusumoto, S.; Aimoto, S.; Kumagaye, K.Y.; Nakajima, K.; Nagata, K. Bioorg. Med. Chem., 1997, 5, 135.
23. Perich, J.W.; Johns, R.B. Synthesis, 1989, 701.
24. Kitas, E.A.; Knorr, R.; Trzeciak, A.; Bannwarth, W. Helv. Chim. Acta, 1991, 74, 1314.
25. Perich, J.W.; Reynolds, E.C. Synlett, 1991, 577.
26. Mora, N.; Lacombe, J.M.; Pavia, A.A. Int. J. Pept. Protein Res., 1995, 45, 53.
27. Fretz, H. Lett. Pept. Sci., 1997, 4, 171.
28. Perich, J.W.; Alewood, P.F.; Johns, R.B. Synthesis, 1986, 572.
29. Bannwarth, W.; Kung, E. Tetrahedron Lett., 1989, 30, 4219.
30. Ueki, M.; Tachibana, J.; Ishii, Y.; Okumura, J.; Goto, M. Tetrahedron Lett., 1996, 37, 4953.
31. Chao, H.-G.; Leiting, B.; Reiss, P.D.; Burkhardt, A.L.; Klimas, C.E.; Bolen, J.B.; Matseuda, G.R. J. Org. Chem., 1995, 60, 7710.
32. Chao, H.-G.; Bernatowicz, M.S.; Reiss, P.D.; Matseuda, G.R. J. Org. Chem., 1994, 59, 6687.
33. Kitas, E.A.; Wade, J.D.; Johns, R.B.; Perich, J.W.; Tregear, G.W. J. Chem. Soc. Chem. Commun., 1991, 338.
34. Wade, J.D.; Bedford, J.; Sheppard, R.D.; Tregear, G.E. Pept. Res., 1991, 4, 194.
35. Wakamiya, T.; Nishida, T.; Togashi, R.; Saruta, K.; Yasuoka, J.; Kusumoto, S. Bull. Chem. Soc. Jpn., 1996, 69, 465.
36. Vorherr, T.; Bannwarth, W. Bioorg. Med. Chem. Lett., 1995, 5, 2661.
37. White, P.; Beythien, J. In Innovations and Perspectives in Solid Phase Synthesis and Combinatorial Libraries; Epton, Ed.; Mayflower Scientific: Birmingham, 1996; pp. 557-560.
38. Handa, B.K.; Hobbs, C.J. J. Pept. Sci., 1998, 4, 138.
39. Folsch, G. Acta Chem. Scand., 1959, 13, 1407.
40. Andrews, D. M.; Kitchin, J.; Seale, P. W. Int. J. Pept. Protein Res., 1991, 38, 469.
41. Perich, J.W.; Ruzzene, M.; Pinna, L.A.; Reynolds, E.C. Int. J. Pept. Protein Res., 1994, 43, 39.
42. Hoffmann, R.; Wachs, W.O.; Berger, R.G.; Kalbitzer, H.-R.; Waidelich, D.; Bayer, E.; Wagner-Redeker, W.; Zeppezauer, M. Int. J. Pept. Protein Res., 1995, 45, 26.
43. Staerkaer, G.; Jakobsen, M.H.; Olsen, C.E.; Holm, A. Tetrahedron Lett., 1991, 32, 5389.
44. Engstroem, U.; Engstroem, A.; Yokote, K.; Heldin, C.-H. In Peptides 1994, Proceedings of the European Peptide Symposium, 23rd, Braga; Maia, H. L. S. Ed.; ESCOM: Leiden, Netherlands, 1994; pp. 741-742.
45. Perich, J.W. Int. J. Pept. Protein Res., 1992, 40, 134.
46. Perich, J.W.; Meggio, F.; Pinna, L.A. Bioorg. Med. Chem., 1996, 4, 143.
47. Perich, J.W. Lett. Pept. Sci., 1996, 3, 127.
48. Koncz, G.; Toth, G.K.; Bokonyi, G.; Keri, G.; Pecht, I.; Medgyesi, D.; Gergely, J.; Sarmay, G. Eur. J. Biochem., 2001, 268, 3898.
49. Laczko, I.; Hollosi, M.; Vass, E.; Hegedus, Z.; Monostori, E.; Toth, G.K. Biochem. Biophys. Res. Commun., 1998, 242, 474.
50. Alewood, P.F.; Palma, S.; Johns, R.B. Aust. J. Chem., 1984, 37, 425.
51. Alewood, P.F.; Perich, J.W.; Johns, R.B. Tetrahedron Lett., 1984, 25, 987.
52. Perich, J.W.; Alewood, P.F.; Johns, R.B. Tetrahedron Lett., 1986, 27, 1373.
53. Perich, J.W.; Valerio, R.M.; Johns, R.B. Tetrahedron Lett., 1986, 27, 1377.
54. Perich, J.W. ACS Sym. Ser., 1991, 444, 161.
55. Perich, J.W.; Johns, R.B. J. Org. Chem., 1988, 53, 4103.
56. Perich, J.W.; Johns, R.B. J. Chem. Soc. Chem. Commun., 1988, 4.
57. Paquet, A.; Johns, M. Int. J. Pept. Protein Res., 1990, 36, 97.
58. Lacombe, J.M.; Andriamanampisoa, F.; Pavia, A.A. Int. J. Pept. Protein Res., 1990, 36, 275.
59. Perich, J.W.; Alewood, P.F.; Johns, R.B. Aust. J. Chem., 1991, 44, 233.
60. Perich, J.W.; Alewood, P.F.; Johns, R.B. Aust. J. Chem., 1991, 44, 253.
61. Perich, J.W.; Valerio, R.M.; Alewood, P.F.; Johns, R.B. Aust. J. Chem., 1991, 44, 771.
62. Perich, J.W.; Johns, R.B. Aust. J. Chem., 1991, 44, 397.
63. Perich, J.W.; Johns, R.B. Aust. J. Chem., 1991, 44, 1683.
64. Perich, J.W.; Kelly, D.P.; Reynolds, E.C. Int. J. Pept. Protein Res., 1992, 40, 81.
65. Perich, J.W.; Johns, R.B.; Reynolds, E.C. Aust. J. Chem., 1992, 45, 385.
66. Perich, J.W.; Johns, R.B. Aust. J. Chem., 1991, 44, 405.
67. Perich, J.W.; Alewood, P.F.; Johns, R.B. Aust. J. Chem., 1991, 44, 377.
68. Perich, J.W.; Johns, R.B. Aust. J. Chem., 1991, 44, 389.
69. Perich, J.W. Methods Enzymol., 1991, 201, 225.
70. Tsukamoto, M.; Kato, R.; Ishiguro, K.; Uchida, T.; Sato, K. Tetrahedron Lett., 1991, 32, 7083.
71. Mora, N.; Lacombe, J.M.; Pavia, A.A. Tetrahedron Lett., 1993, 34, 2461.
72. Wakamiya, T.; Saruta, K.; Yasuoka, J.; Kusumoto, S. Bull. Chem. Soc. Jpn., 1995, 68, 2699.
73. Ueno, Y.; Suda, F.; Taya, Y.; Noyori, R.; Hayakawa, Y.; Hata, T. Bioorg. Med. Chem. Lett., 1995, 5, 823.
74. Larsson, E.; Luning, B.; Reed, J.; Krog-Jensen, C. Acta Chem. Scand., 1996, 50, 1009.
75. Shapiro, G.; Buchler, D.; Dalvit, C.; Frey, P.; Fernandez, M.D.; Gomez-Lor, B.; Pombo-Villar, E.; Stauss, U.; Swoboda, R.; Waridel, C. Bioorg. Med. Chem. Lett., 1996, 6, 409.
76. Shapiro, G.; Buchler, D.; Dalvit, C.; Frey, P.; Fernandez, M.D.; Gomez-Lor, B.; Pombo-Villar, E.; Stauss, U.; Swoboda, R.; Waridel, C. Bioorg. Med. Chem., 1997, 5, 147.
77. Sebastian, D.; Waldmann, H. Tetrahedron Lett., 1997, 38, 2927.
78. Perich, J.W.; Terzi, E.; Carnazzi, E.; Seyer, R.; Trifilieff, E. Int. J. Pept. Protein Res., 1994, 44, 305.
79. Sakamoto, H.; Kodama, H.; Higashimoto, Y.; Kondo, M.; Lewis, M.S.; Anderson, C.W.; Appella, E.; Sakaguchi, K. Int. J. Pept. Protein Res., 1996, 48, 429.
80. Arendt, A.; McDowell, J.H.; Abdulaeva, G.; Hargrave, P.A. Protein Pept. Lett., 1996, 3, 361.
81. Wakamiya, T.; Saruta, K.; Yasuoka, J.; Kusumoto, S. Chem. Lett., 1994, 6, 1099.
82. Perich, J.W.; Ede, N.J.; Eagle, S.; Bray, A.M. Lett. Pept. Sci., 1999, 6, 91.
83. Schlesinger, D.H.; Buku, A.; Wyssbrod, H.R.; Hay, D.I. Int. J. Pept. Protein Res., 1987, 30, 257.
84. Kuyl-Yeheskiely, E.; Tromp, C.M.; van der Marel, G.A.; van Boom, J.H. Tetrahedron Lett., 1987, 28, 4461.
85. Johnson, T.B.; Coward, J.K. J. Org. Chem., 1987, 52, 1771.
86. Otvos, L.; Elekes, I.; Lee, V.M.Y. Int. J. Pept. Protein Res., 1989, 34, 129.
87. de Bont, H.B.A.; Liskamp, R.M.J.; O'Brian, C.A., Erkelens, C.; Veeneman, G.H.; van Boom, J.H. Int. J. Pept. Protein Res., 1989, 33, 115.
88. de Bont, H.B.A.; van Boom, J.H.; Liskamp, R.M.J. Tetrahedron Lett., 1990, 31, 2497.
89. Perich, J.W.; Johns, R.B. Aust. J. Chem., 1990, 43, 1623.
90. Perich, J.W.; Johns, R.B. Aust. J. Chem., 1991, 44, 503.
91. Knapp, D.R., Oatis, J.E.; Papac, D.I. Int. J. Pept. Protein Res., 1993, 42, 259.
92. Shapiro, G.; Swoboda, R.; Stauss, U. Tetrahedron Lett., 1994, 35, 869.
93. Waldmann, H.; Heuser, A.; Schulze, S. Tetrahedron Lett., 1996, 37, 8725.
94. Johnson, T.; Packman, L.C.; Hyde, C.B.; Owen, D.; Quibell, M. J. Chem. Soc. Perkin Trans. 1, 1996, 719.
95. Hormozdiari, P.; Gani, D. Tetrahedron Lett., 1996, 37, 8227.
96. Hoffmann, R.; Tholey, A.; Hoffmann, T.; Kalbitzer, H.R. Int. J. Pept. Protein Res., 1996, 47, 245.
97. Bernhardt, A.; Drewello, M.; Schutkowski, M. J. Pept. Res., 1997, 50, 143.
98. Xu, Q.H.; Ottinger, E.A.; Sole, N.A.; Barany, G. Lett. Pept. Sci., 1997, 3, 333.
99. Perich, J.W. Lett. Pept. Sci., 1998, 5, 49.
100. Kupihar, Z.; Varadi, G.; Monostori, E.; Toth, G.K. Tetrahedron Lett., 2000, 41, 4457.
101. Miyoshi, K.; Otaka, A.; Kaneko, M.; Tamamura, H.; Fujii, N. Chem. Pharm. Bull., 2000, 48, 1230.
102. Coba, M.P.; Turyn, D.; Pena, C. J. Pept. Res., 2003, 61, 17.
103. Kupihar, Z.; Kele, Z.; Toth, G.K. Org. Lett., 2001, 3, 1033.
104. Sickmann, A.; Meyer, H. E. Proteomics, 2001, 1, 200.
105. Hunter, T. Philos. Trans. R. Soc. Lond. B Biol. Sci., 1998, 353, 583-605.
106. Kalume, D.E.; Molina, H.; Pandey, A. Curr. Opin. Chem. Biol., 2003, 7, 64.
107. Manning, G.; Whyte, D.B.; Martinez, R.; Hunter, T.; Sudarsanam, S. Science, 2002, 298, 1912.
108. Patton, W.F. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 2002, 771, 3.
109. Kaufmann, H.; Bailey, J.E.; Fussenegger, M. Proteomics, 2001, 1, 194.
110. Bendt, A.K.; Burkovski, A.; Schaffer, S.; Bott, M.; Farwick, M.; Hermann, T. Proteomics, 2003, 3, 1637.
111. Boyle, W.J.; Vandergeer, P.; Hunter, T. Methods Enzymol., 1991, 201, 110.
112. Vandergeer, P.; Hunter, T. Electrophoresis, 1994, 15, 544.
113. Wang, Y.H.; Fiol, C.J.; Depaoliroach, A.A.; Bell, A.W.; Hermodson, M.A.; Roach, P.J. Anal. Biochem., 1988, 174, 537.
114. Gronborg, M.; Kristiansen, T.Z.; Stensballe, A.; Andersen, J.S.; Ohara, O.; Mann, M.; Jensen, O.N.; Pandey, A. Mol. Cell Proteomics, 2002, 1, 517.
115. Guzman, N.A.; Stubbs, R.J. Electrophoresis, 2001, 22, 3602.
116. Stensballe, A.; Andersen, S.; Jensen, O.N. Proteomics, 2001, 1, 207.
117. Posewitz, M.C.; Tempst, P. Anal. Chem., 1999, 71, 2883.
118. Neville, D.C.A.; Rozanas, C.R.; Price, E.M.; Gruis, D.B.; Verkman, A.S.; Townsend, R.R. Protein Sci., 1997, 6, 2436.
119. Kuroda, I.; Shintani, Y.; Motokawa, M.; Abe, S.; Furuno, M. Anal. Sci., 2004, 20, 1313.
120. Miyazaki, S.; Miah, M.Y.; Morisato, K.; Shintani, Y.; Kuroha, T.; Nakanishi, K. J. Sep. Sci., 2005, 28, 39.
121. Liao, P.C.; Leykam, J.; Andrews, P.C.; Gage, D.A.; Allison, J. Anal. Biochem., 1994, 219, 9.
122. Annan, R.S.; Carr, S.A. Anal. Chem., 1996, 68, 3413.
123. Kjellstrom, S.; Jensen, O.N. Anal. Chem., 2004, 76, 5109.
124. Asara, J.M.; Allison, J. J. Am. Soc. Mass Spectrom., 1999, 10, 35.
125. Janek, K.; Wenschuh, H.; Bienert, M.; Krause, E. Rapid Commun. Mass Spectrom., 2001, 15, 1593.
126. Wells, J.M.; McLuckey, S.A. In Biological Mass Spectrometry, 2005; pp. 148-185.
127. Carr, S.A.; Huddleston, M.J.; Annan, R.S. Anal. Biochem., 1996, 239, 180.
128. Steen, H.; Kuster, B.; Fernandez, M.; Pandey, A.; Mann, M. Anal. Chem., 2001, 73, 1440.
129. Huddleston, M.J.; Annan, R.S.; Bean, M.F.; Carr, S.A. J. Am. Soc. Mass Spectrom., 1993, 4, 710.
130. Bogdanov, B.; Smith, R.D. Mass Spectrom. Rev., 2005, 24, 168.