Orthogonal ligation strategies for peptide and protein

Biopolymers - Peptide Science Section

Volumn 51, Issue 5, 1999, Pages 311-332

  Tam, James P ^a   Yu, Qitao ^a   Miao, Zhenwei ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SYNTHETIC PEPTIDE;

ARTICLE; CIS TRANS ISOMERISM; ENTROPY; MOLECULAR DYNAMICS; PEPTIDE SYNTHESIS; PROTEIN CONFORMATION; REACTION ANALYSIS; STEREOCHEMISTRY;

AMINO ACIDS; LIGANDS; PEPTIDE BIOSYNTHESIS; PEPTIDES; PROTEIN ENGINEERING; PROTEINS;

EID: 0033500546     PISSN: 00063525     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-0282(1999)51:5<311::AID-BIP2>3.0.CO;2-A     Document Type: Article

References (113)

1. Merrifield, R. B. J Am Chem Soc 1963, 85, 2149-2154.
2. Merrifield, R. B. In Peptides: Synthesis, Structures and Applications; Gutte, B., Ed.; Academic Press, San Diego, CA, 1995; pp 93-168.
3. Merrifield, R. B. Science 1986, 57, 1619-1625.
4. Hirschmann, R.; Mutt, R. F.; Veber, D. F; Vitali, R. A.; Varga, S. L.; Jacob, T. A.; Holly, F. W.; Denkewalter, R. C. J Am Chem Soc 1969, 91, 507-508.
5. Kiyama, S.; Fujii, N.; Yajima, H.; Moriga, M.; Takagi, A. Int J Pept Protein Res 1984, 23, 174-186.
6. Hofmann, R.; Smithers, M. J.; Finn, F. M. J Am Chem Soc 1966, 88, 4107.
7. Ramage, R.; Biggin, G. W.; Brown, A. R.; et al. In Innovation and Perspectives in Solid Phase Synthesis and Combinatorial Libraries, Proceedings of the 4th International Symposium on Solid Phase Synthesis and Combinatorial Chemical Libraries; Epton, R., Ed.; Mayflower Scientific Publishers: Kingswinford, UK, 1996; pp 1-10.
8. Quibell, M.; Packman, L. C.; Johnson, T. J Am Chem Soc 1995, 117, 11656-11668.
9. Blake, J.; Li, C. H. Proc Natl Acad Sci. USA 1981, 78, 4055-4058.
10. Blake, J. Int J Pept Protein Res 1986, 27, 191-200.
11. Yamashiro, D.; Li, C. H. Int J Pept Protein Res 1988, 31, 322-334.
12. Aimoto, S.; Mizoguchi, N.; Hojo, H.; Yoshimura, S. Bull Chem Soc Jpn 1989, 62, 524-531.
13. Blake, J. Int J Pept Protein Res 1981, 17, 273-274.
14. Blake, J. Int J Pept Protein Res 1986, 27, 191-200.
15. Ramshara, K.; Li, C. H. J. Int J Pept Protein Res 1986, 28, 468-476.
16. Fournier, A.; Danho, W.; Felix; A. M. J. Int J Pept Protein Res 1989, 33, 133-139.
17. Inui, T.; Bodi, J.; Kubo, S.; Nishio, H.; Kimura, T.; Kojima, S.; Maruta, H.; Muramatsu, T.; Sakakibara, S. J Pept Sci 1996, 2, 28,
18. Li, C. H.; Yamashiro, D. J Am Chem Soc. 1970, 93, 7608-7609.
19. Chao, H.-G.; Bernatowicz, M. S.; Matsueda, G. R. J Org Chem 1993, 58, 2640-2644.
20. Baranay, G.; Merrifield, R. B. J Am Chem Soc 1977, 99, 7363-7365.
21. Kanie, O.; Ito, Y.; Ogawa, T. J Am Chem Soc 1994, 116, 12073-12074.
22. Zeng, F.; Zimmerman, S. C. J Am Chem Soc 1996, 5326-5327.
23. Muir, T.; Dawson, P. E. Kent, S. B. H. Methods Enzymol 1997, 289, 266-298
24. Tam, J. P.; Liu, C-F.; Lu, Y.; Shao, J.; Zhang, L.; Rao, C.; Shin, Y. S. In Peptides: Chemistry, Structure and Biology - Proceedings of the 14th American Peptide Symposium; Kaumaya; P. T. P.; Hodges, R. S., Eds.; Mayflower Worldwide: Kingswinford, UK, 1996; pp 15-16.
25. Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266, 776-779.
26. Liu, C.-F.; Rao, C.; Tam, J. P. In Peptides: Chemistry, Structure and Biology - Proceedings of the 14th American Peptide Symposium; Kaumaya, P. T. P., Hodges, R. S., Eds.; Mayflower Worldwide: Kingswinford, UK, 1996; pp 835-836.
27. Tam, J. P.; Yu, Q. Biopolymer 1998, 46, 319-327.
28. Homandberg, G. A.; Mattis, J. A.; Laskowski, M., Jr. Biochemistry 1978, 17, 5220-5227.
29. Homandberg, G. A.; Laskowski, M., Jr. Biochemistry 1979, 18, 586-592.
30. Homandberg, G. A.; Chaiken, I. M. J Biol Chem 1980, 255, 4903-4909.
31. Dyckes, D. F.; Creighton, T.; Sheppard, R. C. Nature 1974, 247, 202-204.
32. Corradin, G.; Harbury, H. A. Biochem Biophys Res Commun 1974, 61 1400-1406.
33. Proudfoot, A. E. I.; Rose, K.; Wallace, C. J. A. J Biol Chem 1989, 264, 8764-8770.
34. Witte, K.; Sears, P.; Martin, R.; ; Wong C.-H. J Am Chem Soc 1997, 119, 2114-2118.
35. Zhong, Z.; Liu, J. L.-C.; Dinterman, L. M.; Finkelman, M. A. J.; Mueller, W. T.; Rollence, M. L.; Whitlow, M. and Wong, C.-H. J Am Chem Soc 1991, 113, 683-684
36. Sears, P.; Schuster, M.; Wang, P.; Witte, K.; Wong C.-H. J Am Chem Soc 1994, 116, 6521-6530.
37. Shao, J.; Tam, J. P. J Am Chem Soc 1995, 117, 3894-3899.
38. King, T. P.; Zhao, S. W.; Lam, T. Biochemistry 1986, 25, 5774-5779.
39. Geoghegan, K. F.; Stroh, H. G. Bioconjugate Chem 1992, 3, 138-146.
40. Fisch, I.; Künzi, G.; Rose, K.; Offord, R. Bioconjugate Chem 1992, 3, 147-153.
41. Rose, K. J Am Chem Soc 1994, 116, 30-33.
42. Lu, Y.-A.; Clavijo, P.; Galatino, M.; Shen, Z.-Y.; Liu, W.; Tam, J. P. Mol Immunol 1991, 6, 623-630.
43. Robey, F. A.; Fields, R. L. Anal Biochem 1989, 177, 373-377.
44. Gaertner, H. F.; Rose, K.; Cotton, R.; Timms, D.; Camble, R.; Offord, R. E. Bioconjugate Chem 1992, 3, 262-268.
45. Dawson, P. E.; Kent, S. B. H. J Am Chem Soc 1993, 115, 7263-7266.
46. Schnolzer, M.; Kent, S. B. H. Science 1992, 256, 221-225.
47. Brenner, M.; Zimmerman, J. P.; Wehrmüller, J.; Quitt, P.; Photaki, I. Experientia 1955, 11, 397.
48. Wallace, C. J. A. FASEB J 1993, 7, 505-515.
49. Brenner, M.; Zimmermann, J. P.; Wehrmüller, J.; Quitt, P.; Hartmann, A.; Schneider, W.; Beglinger, U. Helv Chem Acta 1957, 40, 1497-1517.
50. Kemp, D. S. Biopolymers 1981, 20, 1793-1804.
51. Fotouhi, N.; Galakatos, N. G.; Kemp, D. S. J Org Chem 1989, 54, 2803-2817.
52. Kemp, D. S.; Carey, R. I. J Org Chem 1993, 58, 2216-2222.
53. Canne, L. E.; Bark, S. J.; Kent, S. B. H. J Am Chem Soc 1996, 118, 5891-5896
54. Tam, J. P.; Lu, Y.-A.; Liu, C. F.; Shao, J. J. Proc Natl Acad Sci. USA 1995, 92, 12485-12489.
55. Jackson, D. Y.; Burnier, J.; Quan, C.; Stanley, M.; Tom, J. Wells, J. A. Science 1994, 266, 243-247.
56. Xu, M.-Q.; Southworth, M. W.; Mersha, F. B.; Hornstra, L. J.; Perler, F. B. Cell 1993, 75, 1371-1377.
57. Xu, M.-Q.; Comb, D. G.; Paulus, H.; Noren, C. J.; Shao, Y.; Perler, F. B. EMBO J; 1994, 13, 5517-5522.
58. Shao, Y.; Paulus, H. J. Peptide Res 1997, 50, 193-198.
59. Chong, S.; Mersha, F. B.; Comb, D. G.; Scott, M. E.; Landry, D.; Vence, L. M.; Perler, F. B.; Benner, J.; Kucera, R. B.; Hirvenen, C. A.; et al. Gene 1997, 271-281.
60. Hanessian, S.; McNaughton, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854.
61. Ratner, S.; Clarke, H. T. J Am Chem Soc 1937, 59, 200-206.
62. Tome, D.; Nauler, N. Int J Pept Protein Res 1981, 17, 501-507.
63. Liu, C. F.; Tam, J. P. J Am Chem Soc 1994, 116, 4149-4153.
64. Liu, C. F.; Tam, J. P. Proc Natl Acad Sci USA 1994, 91, 6584-6588.
65. Liu, C. F.; Rao, C.; Tam, J. P. J Am Chem Soc 1996, 118, 307-312.
66. Liu, C. F.; Rao, C.; Tam, J. P. In Peptides: Chemistry, Structure and Biology. Proceedings of the 13th American Peptide Symposium; Hodges, R. S., J. A. Smith, Eds.; ESCOM: Leiden, 1994; pp 1075-1077.
67. Tam, J. P.; Rao, C.; Shao, J.; Liu, C. F. Int J Pept Protein Res 1994, 45, 209-216.
68. Shao, J.; Tam, J. P. J Am Chem Soc 1995, 117, 3894-3899.
69. Tam, J. P.; Miao, Z. J Am Chem Soc 1999, 121, 9013-9022.
70. Fulop, F.; Marttinen, J.; Pihlaja, K. Tetrahedron 1990, 46, 6545-6552.
71. Baldwin, J. E. Tetrahedron 1982, 38, 2939-2947.
72. Barbas, C. F., III; Matos, J. R.; West, J. B.; Wong, C. H. J Am Chem Soc 1988, 110, 5162.
73. Morihara, K.; Oka, T.; Tsuzuki, H. Nature (London) 1979, 280, 412-413.
74. Hojo, H.; Aimoto, S. Bull Chem Soc Jpn 1991, 64, 111-117.
75. Botti, P.; Pallin, T. D.; Tam, J. P. J Am Chem Soc 1996, 118, 10018-10024.
76. Frechet, M. J.; Schuerch, C. J Am Chem Soc 1971, 93, 492.
77. Geoghegan, K. F.; Stroh, J. G. Bioconjugate Chem 1992, 3, 138-146
78. Kern, D.; Schutkowski, M.; Drakenberg, T. J Am Chem Soc 1997, 119, 8403-8408.
79. Dumy, P.; Keller, M.; Ryan, D. E.; Rohwedder, B.; Wohr, T.; Mutter, M. J Am Chem Soc 1997, 119, 918-925.
80. Seebach, D.; Latmatsch, B.; Amstutz, R.; Beck, A. K.; Dobloer, M.; Egli, M.; Fitzi, R.; Gautschi, M.; Herradon, B.; Hidber, P.; Irwin, J. J.; Locher, R.; Maestro, M.; Maetzke, T.; Mourino, A.; Pfammatter, E.; Plattner, D. A.; Schickli, C.; Schweizer, W. B.; Seiler, P.; Stucky, G. Helv Chim Acta 1992, 75, 913-934.
81. Szilagyi, L.; Gyorgydeak, Z. J Am Chem Soc 1979, 101, 427-432.
82. Parthasarathy, R.; Korrytnyk, W. J Am Chem Soc 1976, 98, 6634-6643.
83. Wurthrich, K. In NMR of Proteins and Nucleic Acids; John Wiley & Sons: New York, 1986; pp 117-125.
84. Bhaskar, B.; DeMoll, E.; Grahame, D. A. Biochemistry 1998, 37, 14491-14499.
85. Jakubowski, H. Biochemistry 1998, 37, 5147-5153.
86. Shiau, C. Y.; Byford, M. F.; Aplin, R. T.; Baldwin, J. E.; Schofield, C. J. Biochemistry 1997, 36, 8798-8806.
87. Wieland, T.; Bokelmann, E.; Bauer, L.; Lang, H. U.; Lau, H. Liebigs Ann Chem 1953, 583, 129-149.
88. Schwyzer, R.; Hurlimann, C. Helv Chim Acta 1954, 37, 155-166.
89. Yamashiro, D.; Blake, J. Int J Peptide Protein Res 1981, 18, 383-392.
90. Wieland, T.; Schneider, G. Liebigs Ann Chem 1953, 583, 159.
91. Muir, T. W.; Sondhi, D.; Cole, P. A. Proc Natl Acad Sci USA 1998, 95, 6705-6710.
92. Severinov, K.; Muir, T. W. J Biol Chem 1998, 273, 16205-16209.
93. Evans, T. C.; Benner, J., Jr.; Xu, M.-Q. J Biol Chem 1999, 274, 3923-3926.
94. Dawson, P. E.; Churchill, M. J.; Ghadiri, M. R.; Kent, S. B. H. J Am Chem Soc 1997, 119, 4325-4329.
95. Burns, J. A.; Butler, J. C.; Moran, J.; Whitesides, G. M. J Org Chem 1991, 56, 2648-2650.
96. Tam, J. P.; Wu, C.-R.; Liu, W.; Zhang, J.-W. J Am Chem Soc 1991, 113, 6657-6662.
97. Tam, J. P.; Lu, Y.-A.; Yu, Q. J Am Chem Soc 1999, 121, 4361-4324.
98. Canne, L. E.; Walker, S. M.; Kent, S. B. H. Tetrahedron Lett 1995, 36, 1217-1220.
99. Zhang, L.; Tam, J. P. J Am Chem Soc 1999, 121, 3311-3320.
100. Li, X.; Kawakami, T.; Aimoto, S. Tetrahedron Lett 1998, 39, 8669-8672.
101. Carey, R. I.; Bordas, L. W.; Slaughter, R. A.; Meadows B. C.; Wadsworth, J. L.; Huang, H.; Smith, J. J.; Furusjo, E. J Peptide Res 1997, 49, 570-581.
102. Liu, C. F.; Rao, C.; Tam, J. P. Tetrahedron Lett 1996, 37, 933-936.
103. Heinrikson, R.L. J Biol Chem 1971, 246, 4090-4096.
104. Naider, F. R.; Becker, J. M. Biopolymers 1997, 43, 3-14.
105. Zhang, L.; Tam, J. P. Tetrahedron Lett 1997, 38, 3-6.
106. Ellman, G. L. Arch Biochem Biophys 1959, 82, 70-77.
107. Hennard, C.; Tam, J. P. In Peptides: Chemistry, Structure and Biology - Proceedings of the 15th American Peptide Symposium; Tam, J. P., Kaumaya, P. T. P., Eds.; Kluwer Academic Press: 1997; pp 247-248.
108. Zhang, L.; Tam, J. P. J Am Chem Soc 1997, 119, 2363-2370.
109. Botti, P.; Pallin, T. D.; Tam, J. P. J Am Chem Soc 1996, 118, 10018-10024.
110. Tam, J. P.; Lu, Y. A. Tetrahedron Lett 1997, 38, 5599-5602.
111. Camarero, J. A.; Muir, T. W. Chem Commun 1997, 1369-1370.
112. Camarero, J. A. Pavel, J.; Muir, T. W. Angew Chem Int Ed 1998, 37, 347-349.
113. Shao, Y.; Lu, W.; Kent, S. B. H. Tetrahedron Lett 1998, 39, 3911-3914.