Peptide chemistry: Development of high performance liquid chromatography and capillary zone electrophoresis

Biopolymers

Volumn 40, Issue 3, 1996, Pages 265-317

  Miller, Charleen ^a   Rivier, Jean ^a  

^a SALK INSTITUTE FOR BIOLOGICAL STUDIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY; ELECTROPHORESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HORMONES; MOLECULES; ORGANIC SOLVENTS; PROTEINS; SIZE EXCLUSION CHROMATOGRAPHY; TISSUE;

CAPILLARY ZONE ELECTROPHORESIS; ION EXCHANGE CHROMATOGRAPHY; SYNTHETIC PEPTIDES; TISSUE EXTRACTS;

AMINO ACIDS;

AMINO ACID SEQUENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; REVIEW; ZONE ELECTROPHORESIS;

AMINO ACID SEQUENCE; ANIMALS; BUFFERS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ELECTROPHORESIS, CAPILLARY; HUMANS; MOLECULAR SEQUENCE DATA; MOLECULAR WEIGHT; PEPTIDES; PROTEIN ENGINEERING; REFERENCE STANDARDS;

EID: 0029837607     PISSN: 00063525     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1097-0282(1996)40:3<265::aid-bip2>3.0.co;2-u     Document Type: Article

References (124)

1. Burgus, R. & Rivier, J. (1976) in Peptides 1976, Fourteenth European Peptide Symposium, Loffet, A., Ed., Bruxelles, Belgium, pp. 85-94.
2. Grushka, E. (1974) Bonded Stationary Phases in Chromatography, Ann Arbor Sciences, Ann Arbor, MI.
3. Brown, P. R. (1973 ) Biochemical and Biomedical Applications. Academic Press, New York - London.
4. Gil-Av, E. (1974) in Peptides, Wolman, Y., Eds., John Wiley & Sons, Israel University Press., New York - Toronto, Jerusalem, pp. 247-256.
5. Yoshida, N., Zimmerman, C. L. & Pisano, J. J. (1975) in Peptides, Walter, R., Meienhofer, J., Eds., Ann Arbor Sciences, Ann Arbor, MI, pp. 955.
6. Hardy, P. M., Prout, R. A. & Rydon, H. N. (1974) J. Chem. Soc. 802.
7. Shechter, I. (1974) Anal. Biochem. 58, 30-38.
8. Pickart, L. R. & Thaler, M. M. (1975) Prep. Biochem. 5, 397-412.
9. Tsuji, K., & Robertson, J. H. (1975 ) J. Chromatog. 112, 663-672.
10. Hancock, W. S., Bishop, C. A. & Hearn, M. T. W. (1976) FEBS Lett. 72, 139-142.
11. Purcell, A. W., Aguilar, M.-I. & Hearn, M. T. W. (1993) Anal. Chem 65, 3038-3047.
12. Aguilar, M. I., Mougos, S., Boublik, J., Rivier, J. & Hearn, M. T. W. (1993) J. Chromatog. 646, 53-65.
13. Zhu, B. Y., Mant, C. T. & Hodges, R. S. (1992) J. Chromatog. 594, 75-86.
14. Jorgensen, E. C., Windridge, G. C. & Lee, T. C. (1970) J. Med. Chem. 13, 352-356.
15. Rivier, J., Wolbers, R. & Burgus, R. (1977) in Proceedings of the Fifth American Peptide Symposium. Goodman, M., & Meienhofer, J. Eds., Halstead Press, John Wiley & Sons, New York, pp. 52-55.
16. Hughes, J., Smith, T. W., Kosterlitz, H. W., Fothergill, L. A., Morgan, B. A. & Morris, H. R. (1975) Nature 258, 577-579.
17. Guillemin, R., Ling, N. & Burgus, R. (1976) CR Acad. Sci. (Paris) 282, 783.
18. Rivier, J., Lazarus, L., Perrin, M. &. Brown, M. (1977) J. Med. Chem. 20, 1409-1412.
19. Rivier, J. & Brown, M. (1978) Biochemistry 17, 1766-1771.
20. Ling, N., Burgus, R. & Guillemin, R. (1976) Proc. Natl. Acad. Sci, USA 73, 3942-3946.
21. Rivier, J., Kaiser, R. & Galyean, R. (1978) Biopolymers 17, 1927-1938.
22. Rivier, J. (1978) J. Liq. Chromatog 1, 343-367.
23. Woods, A. H. & O'Bar, P. R. (1970) Science 167, 179-181.
24. Mayer, M. M. & Miller, J. A. (1970) Anal. Biochem. 36, 91-100.
25. Stern, A. S., Lewis, R. V., Kimura, S., Rossier, J., Gerber, L. D., Brink, L., Stein, S. & Udenfriend, S. (1979) Proc. Netl. Acad. Sci. USA 76, 6680-6683.
26. Sokolowski, A. & Wahlund, K.-G. (1980) J. Chromatog 189, 299-316.
27. Bennet, H. P. J., Hudson, H. M., McMartin, C. & Purdon, G. E. (1977) Biochem J. 168, 9-13.
28. Vale, W., Spiess, J., Rivier, C. & Rivier, J. (1981) Science 213, 1394-1397.
29. Guillemin, R. & Rosenberg, B. (1955) Endocrinology 57, 599-607.
30. Saffran, M. & Schally, A. V. (1955) Can. J. Biochem. Physiol. 33, 408.
31. Rivier, C., Brownstein, M., Spiess, J., Rivier, J. & Vale, W. (1982) Endocrinology 110, 272-278.
32. McCall, S. M. (1957) Endocrinology 60, 664.
33. Portanova, R. & Sayers, G. (1973) Proc. Soc. Exp. Biol. Med. 143, 661-666.
34. Schally, A. V., Huang, W. Y., Redding, T. W., Arimura, A., Coy, D. H., Chihara, K., Chang, R. C. C., Raymond, V. & Labrie, F. (1978) Biochem Biophys. Res. Commun. 82, 582-588.
35. Knudsen, R., Lam, Y. K., Folkers, K., Frick, W., Daves, G. D., Jr., Barofcky, D. F. & Bowers, C. Y. (1978) Biochem. Biophys. Res. Commun. 80, 735-739.
36. Vale, W. & Rivier, C. (1977) Fed. Proc. Fed. Amer. Soc. Exp. Biol. 36, 8.
37. Burgus, R., Amoss, M., Brazeau, P., Brown, M., Ling, N., Rivier, C., Rivier, J., Vale, W. & Villarreal, J. (1976) in Hypothalamus and Endocrine Functions. Labrie, F., Meites, J. & Pelletier. G., Eds., Plenum Press, New York, pp. 355-372.
38. Vale, W. & Rivier, C. (1977) Fed. Proc. 36, 2094-2099.
39. Marki, W., Spiess, J., Tache, Y., Brown, M. & Rivier, J. E. (1981) J. Am. Chem. Soc. 103, 3178-3185.
40. Spiess, J., Rivier, J., Rivier, C. & Vale, W. (1981) Proc. Natl. Acad. Sci. USA 78, 6517-6521.
41. Rivier, J., Spiess, J. & Vale, W. (1983) Proc. Natl Acad. Sci. USA 80, 4851-4855.
42. Shibahara, S., Morimoto, Y., Furutani, Y., Notake, M., Takahashi, H., Shimizu, S., Horikawa, S. & Numa, S. (1983) Embo. J. 2, 775-779.
43. Rivier, J., Spiess, J., Thorner, M. & Vale, W. (1982) Nature 300, 276-278.
44. Vale, W., Vaughan, J., Yamamoto, G., Spiess, J. & Rivier, J. (1983) Endocrinology 112, 1553-1555.
45. Vaughan, J., Donaldson, C., Bittencourt, J., Perrin, M. H., Lewis, K., Sutton, S., Chan, R., Turnbull, A., Lovejoy, D., Rivier, C., Rivier, J., Sawchenko, P. E. & Vale, W. (1995) Nature 378, 287-292.
46. Spiess, J., Rivier, J. & Vale, W. (1983) Nature 303, 532-535.
47. Rivier, J., McClintock, R., Eksteen, R. & Karger, B. L. (1982) in The 1982 FDA-USP Workshop on Drug and Reference Standards for Insulins, Somatropins and Thyroid-axis Drugs. The United States Pharmacopeial Convention, Inc., Ed., Hormone Drugs, Rockville, MD, pp. 554-564.
48. Rivier, J. & McClintock, R. (1989) in The Use of HPLC in Receptor Purification and Characterization, Kerlavage, A. R., Ed., John Wiley & Sons, New York, pp. 77-105.
49. Hancock, W. S., Bishop, C. A., Meyer, L. J., Harding, D. R. K. & Hearn, M. T. W. (1978) J. Chromatogr. 161, 291-302.
50. O'Hare, M. J. & Nice, E. C. (1979) J. Chromatogr. 171, 209-226.
51. Rivier, J. E., Desmond, J., Spiess, J., Perrin, M., Vale, W., Eksteen, R. & Karger, B. (1979) in Peptides: Structure A Biological Function, Sixth American Peptide Symposium. Gross, E. & Meienhofer, J., Eds., Georgetown University, Washington, DC, June 17-22, pp. 125-128.
52. Barany, G. & Merrifield, R. B. (1980) in The Peptides, Analysis, Synthesis, Biology, Gross, E. & Meienhofer, J., Eds., Academic Press, New York, pp. 1-284.
53. Lewis, R. V., Fallon, A., Stein, S., Gibson, K. D. & Undenfriend, S. (1980) Anal. Biochem. 104, 153-159.
54. Powell, J. F. F., Zohar, Y., Elizur, A., Park, C., Fischer, W. H., Craig, A. G., Rivier, J. E., Lovejoy, D. A. & Sherwood, N. M. (1994) Proc. Natl. Acad. Sci USA91, 12081-12085.
55. Habibi, H. R., Peter, R. E., Nahorniak, C. S., Milton, R. C. d. L. & Millar, R. P. (1992) Regul. Peptide 37, 271-284.
56. Schulz, R. W., Bosma, P. T., Zandbergen, M. A., vanDerSanden, M. C. A., VanDijk, W., Peute, J., Bogerd, J. & Goos, H. J. T. (1993) Endocrinology 133, 1569-1577.
57. Sherwood, N. M., Lovejoy, D. A. & Coe, I. R. (1993) Endocrinol. Rev. 14, 241-254.
58. Davis, M. R. & Fernald, R. D. (1990) J. Neurobiol. 21, 1180-1188.
59. Hoeger, C., Brown, M. & Rivier, J. (1990) in Peptides: Chemistry. Structure and Biology. Eleventh American Peplide Symposium, Rivier, J. & Marshall, G., Eds., La Jolla, California, July 9-14, pp. 267-268.
60. Hoeger, C., Galyean, R., Boublik, J., McClintock, R. & Rivier, J. (1987) Biochromatography 2, 134-142.
61. Rivier, J. & McClintock, R. (1983) J. Chromatogr. 268, 112-119.
62. Rivier, J., Spiess, J., Thorner, M. & Vale, W. (1983) Nature 300, 276.
63. Spiess, J., Rivier, J. & Vale, W. (1983) Nature 303, 532-535.
64. Sherwood, N., Eiden, L., Brownstem, M., Spiess, J., Rivier, J. & Vale, W. (1983) Proc. Natl. Acad. Sci. USA 80, 2794-2798.
65. Pearson, J. D. & Regnier, F. E. (1983) J. Liq. Chromatog. 6, 497.
66. Rivier, J. E. (1980) J. Chromalogr. 202, 221-222.
67. Bidlingmeyer, B. A., Deming, S. N., W. P., J. P., Sachok, B. & Petrusek, M. (1979) J. Chromatogr. 186, 419.
68. Rivier, J., Miller, C., Spicer, M., Andrews, J., Porter, J., Tuchscherer, G. & Mutter, M. (1990) in 1st International Symposium on Innovation and Perspectives in Solid Phase Synthesis, Epton, R., Ed. University of Oxford, UK, Aug. 29-Sept. 2, pp. 39-50.
69. Gray, W. R., Rivier, J. E., Galyean, R., Cruz, L. J. & Olivera, B. M. (1983) J. Biol. Chem. 258, 12247-12251.
70. Ramasharma, K., Sairam, M. R., Seidah, N. G., Chretien, M., Manjunath, P., Schiller, P. W., Yamashiro, D. & Li, C. H. (1984) Science 223, 1199-1202.
71. Mason, A. J., Hayflick, J. S., Ling, N., Esch, F., Ueno, N., Ying, S. Y., Guillemin, R., Niall, H. & Seeburg, P. H. (1985) Nature 318, 659-663.
72. Mayo, K. E., Cerelli, G. M., Spiess, J., Rivier, J., Rosenfeld, M. G., Evans, R. M. & Vale, W. (1986) Proc. Natl. Acad. Sci. USA 83, 5849-5853.
73. Gabriel, T. F., Jimenez, M. H., Felix, A. M., Michalewsky, J. & Meienhofer, J. (1977) Int. J. Peptide Protein Res. 9, 129-136.
74. Meyer, L. J., Harding, D. R. & Hancock, W. S. (1981) J. Liquid Chromatogr. 4, 80.
75. Sigler, G., Fuller, W. & Vavrek, R. (1977) in Peptides. Goodman, M. & Meienhofer, J., Eds., Wiley, New York, pp. 471-473.
76. Diaz, J., Guegan, R., Beaumont, M., Benoit, J., Clement, J., Fauchard, C., Galtier, D., Millan, J., Muneaux, C., Muneaux, Y., Vedel, M. & Schwyzcr, R. (1979) Org Chem. 8, 429.
77. Bishop, C., Meyer, L., Harding, D. & Hancock, W. (1981) J. Liq. Chromatog. 4, 661.
78. Rivier, J., Spiess, J., Perrin, M. & Vale, W. (1979) in Biological/Biomedical Application of Liquid Chromatography II, Hawk, G., Ed., Marcel Dekker, New York, pp. 223-241.
79. Rivier, J., Rivier, C., Spiess, J. & Vale, W. (1983) Analyt. Biochem. 127, 258-266.
80. Rivier, J., McClintock, R., Galyean, R. & Anderson, H. (1984) J. Chromatog 288, 303-328.
81. Rivier, J., Galyean, R., Gray, W. R., Azimi-Zonooz, A., McIntosh, J. M., Cruz, L. J. & Olivera, B. M. (1987) J. Biol Chem. 262, 1194-1198.
82. Rivier, J., Galyean, R., Simon, L., Cruz, L., J., Olivera, B. M. & Gray, W. R. (1987) Biochemistry 26, 8508-8512.
83. Hoeger, C. A., Galvean, R., McClintock, R. A. & Rivier, J. E. (1988) in HPLC of Peptides and Procteins: Separation, Analysis, and Conformation. Mant, C. T. & Hodges, R. S., Eds., CRC Press, Boca Raton, FL, pp. 753-764.
84. Hoeger, C., Porter, J., Boublik, J. & Rivier, J. (1989) J. Chromatogr. 404, 307-310.
85. Hoeger, C., Theobald, P., Porter, J., Miller, C., Kirby, D. & Rivier, J. (1991) in Methods in Neurosciences. Conn, P. M., Eds., Academic Press, Orlando, FL, pp. 3-27.
86. Guillemin, R., Brazeau, P., Bohlen, P., Esch, F., Ling, N. & Wehrenberg, W. B. (1982) Science 218, 585-587.
87. Olivera, B. M., Gray, W. R., Zeikus, R., McIntosh, J. M., Varga, J., Rivier, J., deSantos, V. & Cruz, L J. (1985) Science 230, 1338-1343.
88. Karten, M. J. & Rivier, J. E. (1986) Endocrine Rev. 7, 44-66.
89. Dutta, A. S. (1988) Drugs of the Future 13, 43-57.
90. Schmidt, F., Sundaram, K., Thau, R. B. & Bardin, C. W. (1984) Contraception 29, 283-289.
91. Hall, J. E., Brodie, T. D., Badger, T. M., Rivier, J., Vale, W., Conn, P. M. & Crowley, W. F., Jr. (1988) J. Clin. Endocrinol. Metab. 67, 524-531.
92. Rivier, J., Porter, J., Rivier, C. Perrin, M., Corrigan, A., Hook, W. A., Siraganian, R. P. & Vale, W. W. (1986) J. Med. Chem. 29, 1846-1851.
93. Urban, R. J., Pavlou, S. N., Rivier, J. E., Vale, W. W., Dufau, M. L. & Veldhuis, J. D. (1990), Am. J. Obstet. Gynecol. 162, 1255-1260.
94. Theobald, P., Porter, J., Rivier, C., Corrigan, A., Perrin, M., Vale, W. & Rivier, J. (1991) J. Med. Chem. 34, 2395-2402.
95. Rivier, J. E., Jiang, G., Porter, J., Hoeger, C., Craig, A. G., Corrigan, A., Vale, W. & Rivier, C. L. (1994) J. Med. Chem. 37, 1450-1459.
96. Kirkland, J. J., van Straten, M. A. & Claessens, H. A. (1995) J. Chramatog. 691, 3-19.
97. Miller, C., Hernandez, J.-F., Craig, A. G., Dykert, J. & Rivier, J. (1991) Anal. Chim. Acta 249, 215-225.
98. Ivy, A. C. & Oldberg, E. (1928) Am. J. Physiol. 86, 599-613.
99. Reeve, J. R., Jr., Eysselein, V., Walsh, J. H., Ben-Avram, C. M. & Shively, J. E. (1986) J. Biol. Chem. 261, 16392-16397.
100. Liddle, R. A., Goldfine, I., Rosen, M. S., Taplitz, R. A. & Williams, J. A. (1985) J. Clin. Invest. 75, 1144-1152.
101. Mutt, V. & Jorpes, J. E. (1971) Biochemistry 125, 57P-58P.
102. Eysselein, V. E., Reeve, J. R., Jr., Shively, J. E., Hawke, D. & Walsh, J. H. (1982) Peptides 3, 687-691.
103. Eysselein, V. E., Eberlein, G. A., Shaeffer, M., Grandt, D., Goebell, H., Niebel, W., Rosenquist, G. L., Meyer, H. E. & Reeve, J. R. (1990) Am. J. Physiol. G253-G260.
104. Miranda, M. T. M., Craig, A. G., Miller, C., Liddle, R. A. & Rivier, J. (1993) J. Protein Chem. 12, 533-544.
105. Mutter, M., Tuchscherer, G. G., Miller, C., Altmann, K.-H., Carey, R. I., Wyss, D. F., Labhardt, A. M. & Rivier, J. E. (1992) J. Am. Chem. Soc. 114, 1463-1470.
106. Yamashiro, D. (1964) Nature 201, 76-77.
107. Cooper, A. R. & Deveer, D. S. V. (1978) J. Liq. Chromatog. 1, 693.
108. Rivier, J., Desmond, J., Spiess, J., Perrin, M., Vale, W., Eksteen, R. & Karger, B. L. (1980) in Peptides: Structure and Biological Function, Gross, E. & Meienhofer, S., Eds., Pierce, Rockford, IL, pp. 125-128.
109. Miranda, M. T. M., Miller, C., Craig, A. G., Dykert, J., Liddle, R. A. & Rivier, J. E. (1993) in 13th American Pepiide Symposium, Edmonton, Alberta, Canada, June 20-25, pp. 2-24.
110. Simon, R. J., Kania, R. S., Zuckermann, R. N., Huebner, V. D., Jewll, D. A., Banville, S., Ng, S., Wang, L., Rosenberg, S., Marlowe, C. K., Spellmeyer, D. C., Tan, R., Frankel, A. D., Santi, D. V., Cohen, F. E. & Bartlett, P. A. (1992) Proc. Natl. Acad. Sci. USA 89, 9367-9371.
111. Simon, R. J., Martin, E. J., Miller, S. M., Zuckermann, R. N., Blaney, J. M. & Moos, W. H. (1994) in Techniques in Protein Chemistry V. Crabb, J. W., Ed., Academic Press, San Diego, CA, pp. 533-539.
112. Gordon, T. D., Singh, J., Hansen, P. E. & Morgan, B. A. (1993) Tetrahedr. Lett. 34, 1901-1904.
113. Kim, B. H., Chung, Y. J., Keum, G., Kim, J. & Kim, K. (1992) Tetrahedr. Lett. 33, 6811-6814.
114. Moran, E, J., Wilson, T. E., Cho, C. Y., Cherry, S. R. & Schultz, P. G. (1995) Biopolymers 37, 213-219.
115. Smith, A. B., III, Hirschmann, R., Pasternak, A., Akaishi, R., Guzman, M. C., Jones, D. R., Keenan, T. P., Sprengeler, P. A., Derke, P. L., Emini, E. A., Holloway, M. K. & Schleif, W. A. (1994) J. Med. Chem 37, 215-218.
116. Hagihara, M., Anthony, N. J., Stout, T. J., Clardy, J. & Schreiber, S. L. (1992) J. Am. Chem. Soc. 114, 6568-6870.
117. Spatola, A. F. (1983) in Chemistry and Biochemistry of Amino Acids, Peptides and Proteins. Weinstein, B., Ed., Marcel Dekker, New York, pp. 267-307.
118. Kazmierski, W. M., Urbanczyk-Lipkowska, Z. & Hruby, V. J. (1994) J. Org. Chem. 59, 1789-1795.
119. Rivier, J. E., Jiang, G.-C., Simon, L., Koerber, S. C., Porter, J., Craig, A. G. & Hoeger, C. A. (1996) in Peptides: Chemistry, Structure and Biology, The 14th American Peptide Symposium, Kaumaya, P. T. P., Hodges, R. S., Eds., Columbus, OH, June 18-23, 1995, pp. 275-277.
120. Rivier, J. E., Jiang, G.-C., Koerber, S. C., Porter, J., Craig, A. G. & Hoeger, C. (1996) Proc. Natl. Acad. Sci USA 93, 2031-2036.
121. Hoeger, C. A., Jiang, G.-C., Koerber, S. C., Reisine, T., Liapakis, G. & Rivier, J. E. (1996) in The 14th American Peptide Symposium. Kaumaya, P. T. P., Hodges, R. S., Eds., Columbus, OH, June 18-23, 1995.
122. Schmidt, A. B. & Fine, R. M. (1994) Mol. Sim. 13, 347-365.
123. Kirby, D. A., Boublik, J. H. & Rivier, J. E. (1993) J. Med. Chem. 36, 3802-3808.
124. Kirby, D. A., Miller, C. L. & Rivier, J. E. (1993) J. Chromatogr. 648, 257-265.