Prediction of Difficult Sequences in Solid-Phase Peptide Synthesis

Journal of the American Chemical Society

Volumn 112, Issue 16, 1990, Pages 6039-6046

  Milton, R C D E L ^a   Milton, Saskia C F ^a   Adams, Paul A ^a  

^a UNIVERSITY OF CAPE TOWN   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; NONHUMAN; PEPTIDE SYNTHESIS; THEORETICAL STUDY;

EID: 0025042614     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00172a020     Document Type: Article

References (76)

1. Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149-54.
2. Merrifield, R. B. Science 1986, 232, 341-7.
3. Gutte, B.; Merrifield, R. B. J. Biol. Chem. 1971, 246, 1922-41.
4. Clark-Lewis, L.; Aebersold, R.; Zittener, H.; Schrader, J. W.; Hood, L. E.; Kent, S. B. H. Science 1986, 231, 134-9.
5. Kent, S. B. H. Annu. Rev. Biochem. 1988, 57, 959-89.
6. Barany, G.; Kneib-Cordonier, N.; Mullen, D. G. Int. J. Pept. Protein Res. 1987, 30, 705-39.
7. Kent, S. B. H.; Clark-Lewis, I. In Synthetic Peptides in Biology and Medicine; Alitalo, K., Partanen, P., Vaheri, A., Eds.; Elsevier Science Publishers B.V.: Amsterdam, 1985; pp 29-57.
8. Kent, S. B. H. In Peptides: Structure and Function. Proceedings of the 9th American Peptide Symposium; Deber, C. M., Hruby, V. J., Kopple, K. D., Eds.; Pierce Chemical Co.: Rockford, IL, 1985; pp 407-14.
9. Hancock, W. S.; Prescott, D. J.; Vageios, P. R.; Marshall, R. J. Org. Chem. 1973, 38, 774-81.
10. Atherton, E.; Woolley, V.; Sheppard, R. C. J. Chem. Soc., Chem. Commun. 1980, 970-1.
11. Atherton, E.; Sheppard, R. C. In Peptides: Structure and Function. Proceedings of the 9th American Peptide Symposium; Deber, C. M., Hruby, V. J., Kopple, K. D., Eds.; Pierce Chemical Co.: Rockford, IL, 1985; pp 415-8.
12. Cameron, L. R.; Holder, J. L.; Meldal, M.; Sheppard, R. C. J. Chem. Soc., Perkin Trans. 1 1988, 2895-901.
13. Hudson, D. J. Org. Chem. 1988, 53, 617-24.
14. Kent, S. B. H.; Hood, L. E.; Beilan, H.; Meister, S.; Geiser, T. Peptides 1984. Proceedings of the 18th European Peptide Symposium; Ragnarsson, U., Ed.; Almqvist and Wiksell: Stockholm, 1984; pp 185-8.
15. Meister, S. M.; Kent, S. B. H. In Peptides: Structure and Function. Proceedings of the 8th American Peptide Symposium; Hruby, V. J., Rich, D. H., Eds.; Pierce Chemical Co.: Rockford, IL, 1984; pp 103-6.
16. Stewart, J. M.; Young, J. D. Solid Phase Peptide Synthesis, 2nd ed.; Pierce Chemical Co.: Rockford, IL, 1984; p 46.
17. Live, D.; Kent, S. B. H. In Elastomers and Rubber Elasticity; Mark, J. E., Lai, J., Eds.; ACS Symposium Series 193; American Chemical Society: Washington, DC, 1982; pp 501-15.
18. Flory, P. J. Principles of Polymer Chemistry; Cornell University Press: Ithaca, NY, 1953.
19. Sarin, V. K.; Kent, S. B. H.; Merrifield, R. B. J. Am. Chem. Soc. 1980, 102, 5463-70.
20. Live, D. H.; Kent, S. B. H. In Peptides; Structure and Function. Proceedings of the 8th American Peptide Symposium; Hruby, V. J., Rich, D. H., Eds.; Pierce Chemical Co.: Rockford, IL, 1984; pp 65-8.
21. Deber, C. M.; Lutek, M. K.; Heimer, E. P.; Felix, A. M. Pept. Res. 1989, 2, 184-8.
22. Milton, R. C. de L.; Wormald, P. J.; Brandt, W.; Millar, R. P. J. Biol. Chem. 1986, 261, 16990-7.
23. Ford, W. T.; Balakrishnan, T. Macromolecules 1981, 14, 284-92.
24. Narita, M.; Doi, M.; Sugasawa, H.; Ishikawa, K. Bull. Chem. Soc. Jpn. 1985, 58, 1473-9.
25. Narita, M.; Ogura, T.; Sato, K.; Honda, S. Bull. Chem. Soc. Jpn. 1986, 59, 2433-8.
26. Miyazawa, T.; Blout, E. J. J. Am. Chem. Soc. 1961, 83, 712-9.
27. Narita, M.; Fukunaga, T.; Wakabayashi, A.; Ishikawa, K.; Nakano, H. Int. J. Pept. Protein Res. 1984, 23, 306-14.
28. Bodansky, M. Principles of Peptide Synthesis; Springer-Verlag: Berlin, 1984; p 209.
29. Narita, M.; Ishikawa, K.; Chen, J.-Y.; Kim, Y. Int. J. Pept. Protein Res. 1984, 24, 580-7.
30. Narita, M.; Ohkawa, N.; Nagasawa, S.; Isokawa, S. Int. J. Pept. Protein Res. 1984, 24, 129-34.
31. Narita, M.; Honda, S.; Umeyama, H.; Obana, S. Bull. Chem. Soc. Jpn. 1988, 61, 281-4.
32. Mutter, M.; Hagenmeier, H.; Bayer, E. Angew. Chem., Int. Ed. Engl. 1971, 10, 811-2.
33. Bayer, E.; Mutter, M. Nature 1972, 237, 512-3.
34. Pillai, V. N. R.; Mutter, M. Acc. Chem. Res. 1981, 14, 122-30.
35. Chou, P. Y.; Fasman, G. D. In Advances in Enzymology; Meister, A., Ed.; John Wiley and Sons: New York, 1978; Vol. 47, pp 45-148.
36. Tanaka, S.; Scheraga, H. A. Macromolecules 1976, 9, 142-59.
37. Taylor, R.; Kennard, O.; Versichel, W. J. Am. Chem. Soc. 1983, 105, 5761-6.
38. Baker, E. N.; Hubbard, R. E. Prog. Biophys. Mol. Biol. 1984, 44, 97-179.
39. Schultz, G. E. Annu. Rev. Biophys. Chem. 1988, 17, 1-21.
40. ltoh, K.; Katabuchi, H. Biopolymers 1973, 12, 921-9.
41. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Anal. Biochem. 1970, 34, 595-8.
42. Kaiser, E.; Bossinger, C. D.; Colescott, R. L.; Olsen, D. B. Anal. Chim. Acta 1980, 118, 149-51.
43. Sarin, V. K.; Kent, S. B. H.; Tam, J. P.; Merrifield, R. B. Anal. Biochem. 1981, 117, 147-57.
44. Castro, B.; Dormoy, J. R.; Evin, G.; Solve, C. Tetrahedron Lett. 1975, 1219-22.
45. Morrell, J. L.; Brown, J. H. Int. J. Pept. Protein Res. 1985, 26, 49-54.
46. Erickson, B. W.; Merrifield, R. B. In The Proteins, 3rd ed.; Neurath, H., Hill, R. L., Boeder, C. L., Eds.; Academic Press: New York, 1976; pp 255-590.
47. Barany, G.; Merrifield, R. B. In The Peptides; Gross, E., Meienhofer, J., Eds.; Academic Press: New York, 1980; Vol. 2, pp 1-284.
48. Stewart, J. M.; Young, J. D. Solid Phase Peptide Synthesis, 1st ed.; W. H. Freeman and Co.: San Francisco, CA, 1969.
49. Wilkes, B. C.; Hruby, V. J.; Sherbrooke, W. C.; Castrucci, A. M. de L.; Hadley, M. E. Biochem. Biophys. Res. Commun. 1984, 122, 613-9.
50. Atherton, E.; Clive, D. I. J.; Sheppard, R. C. J. Am. Chem. Soc. 1975, 97, 6584-5.
51. Eberle, A. N.; Atherton, E.; Dryland, A.; Sheppard, R. C. J. Chem. Soc., Perkin Trans. 1 1986, 361-7.
52. Cameron, L.; Meldal, M.; Sheppard, R. C. J. Chem. Soc., Chem. Commun. 1987, 270-2.
53. Atherton, E.; Holder, J. L.; Meldal, M.; Sheppard, R. C.; Valerio, R. M. J. Chem. Soc., Perkin Trans. 1 1988, 2887-94.
54. Kent, S. B. H.; Merrifield, R. B. Peptides 1980. Proceedings of the 16th European Peptide Symposium; Brunfeldt, K., Ed.; Scriptor: Copenhagen, 1981; pp 328-33.
55. Milton, S. C. F.; Milton, R. C. de L. Int. J. Pept. Protein Res. In press.
56. Stewart, J. M.; Klis, W. A. In Innovation and Perspectives in Solid Phase Synthesis; Epton, R., Ed.; Wolverhampton Polytechnic: Wolverhampton, UK. In press.
57. Narita, M.; Ishikawa, K.; Nakano, H.; Isokawa, S. Int. J. Pept. Protein Res. 1984, 24, 14-24.
58. Weygand, F.; Steglich, W.; Bjarnason, J.; Akhtar, R.; Khan, N. M. Tetrahedron Lett. 1966, 3483-7.
59. Weygand, F.; Steglich, W.; Bjarnason, J.; Akhtar, R.; Chytil, N. Chem. Ber. 1968, 101, 3623-41.
60. Weygand, F.; Steglich, W.; Bjarnason, J. Chem. Ber. 1968, 101, 3642-8.
61. Pietta, P. G.; Biondi, P. A.; Brenna, O. J. Org. Chem. 1976, 41, 703-4.
62. Olsen, R. K. J. Org. Chem. 1970, 35, 1912-5.
63. Horiki, K.; Igano, K.; Inouye, K. Chem. Lett. 1978, 165-8.
64. Mitchell, A. R.; Kent, S. B. H.; Engelhard, M.; Merrifield, R. B. J. Org. Chem. 1978, 43, 2845-52.
65. Tam, J. P.; Kent, S. B. H.; Wong, T. W.; Merrifield, R. B. Synthesis 1979, 12, 955-7.
66. Gisin, B. F. Helv. Chim. Acta 1973, 56, 142-3.
67. Milton, R. C. de L.; Mayer, E.; Walsh, J. H.; Rivier, J. E.; Dykert, J.; Lee, T. D.; Shively, J. E.; Reeve, J. R. Int. J. Pept. Protein Res. 1988, 32, 141-52.
68. Rivier, J.; Kaiser, R.; Galyean, R. Biopolymers 1978, 17, 1927-38.
69. Stewart, J. M.; Young, J. D. Solid Phase Peptide Synthesis, 2nd ed.; Pierce Chemical Co.: Rockford, IL, 1984; p 80.
70. Stewart, J. M.; Young, J. D. Solid Phase Peptide Synthesis, 2nd ed.; Pierce Chemical Co.: Rockford, IL, 1984; p 82.
71. Yamashiro, D.; Blake, J.; Li, C. H. Tetrahedron Lett. 1976, 1469-72.
72. Tam, J. P.; Heath, W. F.; Merrifield, R. B. J. Am. Chem. Soc. 1983, 105, 6442-55.
73. Rivier, J.; McClintock, R.; Galyean, R.; Anderson, H. J. Chromatogr. 1984, 288, 303-28.
74. Bidlingmeyer, B. A.; Cohen, S. A.; Tarvin, T. L. J. Chromatogr, 1984, 336, 93-104.
75. Brandt, W. F.; Aik, H.; Chauhan, M.; von Holt, C. FEBS Leu. 1984, 174, 228-32.
76. Seki, S.; Kambara, H.; Naoki, H. Org. Mass Spectrom. 1985, 20, 18-24.