Design and synthesis of novel nonpolar host peptides for the determination of the 310- and α-helix compatibilities of α-amino acid building blocks: An assessment of α,α-disubstituted glycines

Biopolymers - Nucleic Acid Sciences Section

Volumn 42, Issue 5, 1997, Pages 575-626

  Obrecht, Daniel ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CONFORMATIONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

CIRCULAR DICHROISM; PEPTIDES;

POLYPEPTIDES;

GLYCINE; PEPTIDE;

ARTICLE; CIRCULAR DICHROISM; CONFORMATIONAL TRANSITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDE SYNTHESIS; PROTEIN CONFORMATION; X RAY ANALYSIS;

EID: 0031259945     PISSN: 00063525     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1097-0282(19971015)42:5<575::aid-bip7>3.0.co;2-n     Document Type: Article

References (93)

1. Pauling, L., Corey, R. B. & Branson, H. R. (1951) Proc. Natl. Acad. Sci. USA 37, 205-211.
2. Toniolo, C. & Benedetti, E. (1991) Trends Biochem. Sci. 16, 350-353.
3. Barlow, D. J. & Thomton, J. M. (1988) J. Mol. Biol. 201, 601-619.
4. Rose, G. D., Gierasch, L. M. & Smith, J. A. (1985) Adv. Protein Cliem. 37, 1-109.
5. Ramachandran, G. N. & Sasisekharan, V. (1968) Adv. Protein Cliem. 23, 283-437.
6. Karle, I. L. & Balaram, P. (1990) Biochemistry 29, 6747-6761.
7. Zimm, B. H. & Bragg, W. K. (1959) J. Cliem. Phys. 31, 526-535.
8. Richardson, J. S. (1981) Adv. Protein Chem. 34, 167-339.
9. Dill, K. (1990) Biochemistry 29, 7133-7155.
10. Creighton, T. E. & Kim, P. S. (1991) Curr. Op. Str. Biol. 1, 3-4.
11. Jaenicke, R. (1991) Biochemistry 30, 3147-3161.
12. Schultz, G. E. & Schirmer, R. H. (1979) Principles of Protein Structure, New York, Springer-Verlag.
13. Chou, P. Y. & Fasman, G. D. (1974) Biochemistry 13, 211-222.
14. Greenfield, N. & Fasman, G. D. (1969) Biochemistry 8, 4108-4116.
15. Lesk, A. M. (1991) Nature 352, 379-380.
16. Padmanabhan, S., Marqusee, S., Ridgeway, T., Laue, T. M. & Baldwin, R. L. (1990) Nature 344, 268-270.
17. Merutka, G. & Stellwagen, E. (1990) Biochemistry 29, 894-898.
18. Lyu, P.C., Wang, P.C., Liff, M. I. & Kallenbach, N. R. (1991) J. Am. Cliem. Soc. 113, 3568-3572.
19. Mutter, M., Maser, F., Altmann, K.-H., Toniolo, C. & Bonora, G. M. (1985) Biopolymers 24, 1057-1074.
20. Bryson, J. W., Betz, S. F., Lu, H. S., Suich, D. J., Zhou, H. X., O'Neil, K. T. & DeGrado, W. F. (1995) Science 270, 935-941.
21. O'Neil, K. T. & DeGrado, W. F. (1990) Science 250, 646-651.
22. Serrano, L., Sancho, J., Hirschberg, M. & Fersht, A. R. (1992) J. Mol. Biol. 227, 544-560.
23. Karle, I. L., Flippen-Anderson, J. L., Gurunath, R. & Balaram, P. (1994) Protein Sci. 3, 1547-1555.
24. Pavone, V., Bencdetti, E., Di Blasio, B., Pedone, C., Santini, A., Bavoso, A., Toniolo, C., Crisma, M. & Sartore, L. (1990) J. Biomol. Struct. Dynam. 7, 1321-1331.
25. Bosch, R., Jung, G., Voges, K.-P. & Winter, W. (1984) Liebigs Ann. Chcm. 1117-1128.
26. Bosch, R., Jung, G., Schmitt, H., Sheldrick, G. M. & Winter, W. (1984) Angew. Chem. 96, 440-443.
27. Bosch, R., Voges, K.-P., Jung, G. & Winter, W. (1983) Acta Cryst. C39, 481-483.
28. Bosch, R., Jung, G. & Winter, W. (1983) Acta Cryst. C39, 776-778.
29. Bosch, R., Jung, G., Schmitt, H., Winter, W. & Voges, K.-P. (1985) Biopolymers 24, 961-978.
30. Bosch, R., Jung, G., Schmitt, H. & Winter, W. (1985) Biopolymers 24, 979-999.
31. Mayr, W., Oekonomopulos, R. & Jung, G. (1979) Biopolymers 18, 425-450.
32. Oekonomopulos, R. & Jung, G. (1980) Biopolymers 19, 203-214.
33. Jung, G., Bruckner, H., Bosch, R., Winter, W., Schaal, H. & Strähle, J. (1983) Liebigs Ann. Chem. 1096-1106.
34. Jung, G., Bosch, R., Katz, E., Schmitt, H. & Voges, K.-P. (1983) Biopolymers 22, 241-246.
35. Hummel, R.-P., Toniolo, C. & Jung, G. (1987) Angew. Chem. 99, 1180-1181.
36. Butters, T., Hütter, P., Jung, G., Pauls, N., Schmitt, H., Sheldrick, G. M. & Winter, W. (1981) Angew. Chem. 93, 904-905.
37. Toniolo, C. & Benedetti, E. (1991) Macromolecules 24, 4004-4009.
38. Spiegier, C.E. (1993) Ph.D. thesis, University of Zürich.
39. Obrecht, D., Spiegier, C., Schönholzer, P., Müller, K., Heimgartner, H. & Stierli, F. (1992) Helv. Chim. Acta 75, 1666-1696.
40. Hanson, P., Martinez, G., Millhauser, G., Formaggio, F., Crisma, M., Toniolo, C. & Vita, C. (1996) J. Am. Chem. Soc. 118, 271-272.
41. Bindra, V. A. & Kuki, A. (1994) Int. J. Peptide Protein Res. 44, 539-348.
42. Benedetti, E., Barone, V., Bavoso, A., Di Blasio, B., Lelj, F., Pavone, V., Pedone, C., Bonora, C. M., Toniolo, C., Leplawy, M. T., Kaczmarek, K. & Redlinski, A. (1988) Biopolymers 27, 357-371.
43. Benedetti, E., Toniolo, C., Hardy, P., Barone, V., Bavoso, B., Di Blasio, B., Grimaldi, P., Lelj, F., Pavone, V., Pedone, C., Bonora, G. M. & Lingham, I. (1984) J. Am. Chem. Soc. 106, 8146-8152.
44. Crisma, M., Valle, G., Toniolo, C., Prasad, S., Rao, R. B. & Balaram, P. (1995) Biopolymers 35, 1-9.
45. Di Blasio, B., Pavone, V., Pedone, C., Lombardi, A. & Benedetti, E. (1993) Biopolymers 33, 1037-1049.
46. Bosch, R., Bruckner, H., Jung, G. & Winter, W. (1982) Tetrahedron 38, 3579-3583.
47. Wipf, P., Kunz, R. W., Prcwo, R. & Heimgartner, H. (1988) Helv. Cliim. Acta 71, 268-273.
48. Toniolo, C., Crisma, M., Formaggio, F., Valle, G., Cavicchioni, G., Precigoux, G., Aubry, A. & Kamphuis, J. (1993) Biopolymers 33, 1061-1072.
49. Pavone, V., Di Blasio, B., Lombardi, A., Maglio, O., Isernia, C., Pedone, C., Benedetti, E., Altmann, E. & Mutter, M. (1993) Int. J. Peptide Protein Res. 41, 15-20.
50. Altmann, K.-H., Altmann, E. & Mutter, M. (1992) Helv. Chim. Acta 75, 1198-1210.
51. Obrecht, D., Bohdal, U., Daly, J., Lehmann, C., Schönholzer, P. & Müller, K. (1995) Tetrahedron 51, 10883-10900.
52. Bohdal, U.W. (1996) Ph.D. thesis, University of Zürich.
53. Obrecht, D., Lehmann, C., Ruffieux, R., Schönholzer, P. & Müller, K. (1995) Helv. Chim. Acta 78, 1567-1587.
54. Ruffieux, R. S. (1993) Ph.D. thesis, University of Zürich.
55. Polese, A., Formaggio, F., Crisma, M., Valle, G., Toniolo, C., Bonora, G. M., Broxterman, Q. B. & Kamphuis, J. (1996) Cliem. Eur. J. 2, 1104-1111.
56. Valle, G., Crisma, M., Bonora, G. M., Toniolo, C., Lelj, F., Barone, V., Fraternali, F., Hardy, P. M., Langran-Goldsmith, A. & Maia, H. L. S. (1990) J. Chem. Soc. Perkin Trans. 2, 1481-1487.
57. Obrecht, D., Bohdal, U., Broger, C., Bur, D., Lehmann, C., Ruffieux, R., Schönholzer, P., Spiegler, C. & Müller, K. (1995) Helv. Chim. Acta 78, 563-580.
58. Obrecht, D., Karajiannis, H., Lehmann, C., Schönholzer, P., Spiegler, C. & Müller, K. (1995) Helv. Chim. Acta 78, 703-714.
59. Karajiannis, H. (1994) Ph.D. thesis, University of Bern.
60. Smythe, M. L., Houston, S. E. & Marshall, G. R. (1995) J. Am. Chem. Soc. 117, 5445-5452.
61. Moretto, V., Crisma, M., Bonora, G. M., Toniolo, C., Balaram, H. & Balaram, P. (1989) Macromolecules 22, 2939-2944.
62. Narita, M., Doi, M., Sugasawa, H. & Ishikawa, K. (1985) Bull. Chem. Soc. Jpn. 58, 1473-1479.
63. Pavone, V., Di Blasio, B., Santini, A., Benedetti, E., Pedone, C., Toniolo, C. & Crisma, M. (1990) J. Mol. Biol. 214, 633-635.
64. Perczel, A., Hollösi, M., Tusnady, G. & Fasman, G. D. (1991) Protein Eng. 4, 669-679.
65. Perczel, A., Park, K. & Fasman, G. D. (1992) Proteins Struct. Fund. Genet. 13, 57-69.
66. Fasman, G. D. (1995) Biopolymers 37, 339-362.
67. Obrecht, D., Bohdal, U., Ruffieux, R. & Müller, K. (1994) Helv. Chim. Acta 77, 1423-1429.
68. Wipf, P. (1987) Ph.D. thesis, University of Zürich.
69. Boger, D. & Yohannes, D. (1990) J. Org. Chem. 55, 6000-6017.
70. Lloyd-Williams, P., Jou, G., Albericio, F. & Giralt, E. (1991) Tetrahed. Lett. 32, 4207-4210.
71. Hanessian, S. & Lavallee, P. (1975) Can. J. Chem. 53, 2975-2977.
72. Still, W. C., Kahn, M. & Mitra, A. (1978) J. Org. Chem. 43, 2923-2925.
73. Knorr, R., Trzeciak, A., Bannwarth, W. & Gillessen, D. (1989) Tetrahed. Lett. 30, 1927-1930.
74. Karle, I. L. (1989) Biopolymers 28, 1-14.
75. Toniolo, C. (1990) Int. J. Peptide Protein Res. 35, 287-300.
76. Brahms, S. & Brahms, J. (1980) J. Mol. Biol. 138, 149-178.
77. Johnson, W. C., Jr. (1988) Ann. Rev. Biophys. Biophys. Chem. 17, 145-166.
78. Yang, J. T., Wu, C. C. & Martinez, H. M. (1986) Methods Enzymol. 130, 208-269.
79. Chen, Y.-H., Yang, J. T. & Chan, K. H. (1974) Biochemistry 13, 3350-3359.
80. Toniolo, C., Bonora, G. M. & Salardi, S. (1981) Int. J. Biol. Macromol. 3, 377.
81. Woody, R. W. (1974) in Pep tides, Polypeptides and Proteins, Blout, E. R., Bovey, F. A., Goodman, M. & Lotan, N., Eds., Wiley, New York, pp. 338-350.
82. Perczel, A., Hollosi, M., Foxman, B. M. & Fasman, G. D. (1991) J. Am. Chem. Soc. 113, 9772-9784.
83. Toniolo, C., Polese, A., Formaggio, F., Crisma, M. & Kamphuis, J. (1996) J. Am. Chem. Sac. 118, 2744-2745.
84. Johnson, W. C., Jr. & Tinoco, I., Jr. (1972) J. Am. Chem. Soc. 94, 4389-4390.
85. Shoemaker, K. R., Fairman, R., Schultz, D. A., Robertson, A. D., York, E. J., Stewart, J. M. & Baldwin, R. L. (1990) Biopolymers 29, 1-11.
86. Pintar, A., Chollet, A., Bradshaw, C., Chaffotte, A., Cadieux, C., Rooman, M. J., Hallenga, K., Knowles, J., Goldberg, M. & Wodack, S. J. (1994) Biochemistry 33, 11158-11173.
87. Toniolo, C. (1985) in Chemistry and Biochemistry of Amino Acids, Barrett, G. C., Ed., Chapman and Hall, London, pp. 545-572.
88. Manning, M. C. & Woody, R. W. (1991) Biopolymers 31, 569-586.
89. Hanson, P., Millhauser, G., Formaggio, F., Crisma, M. & Toniolo, C. (1996) J. Am. Chem. Soc. 118, 7618-7625.
90. Augspurger, J. D., Bindra, V. A., Scheraga, H. A. & Kuki, A. (1995) Biochemistry 34, 2566-2576.
91. Basu, G. & Kuki, A. (1993) Biopolymers 33, 995-1000.
92. Wuthrich, K. (1986) NMR of Proteins and Nucleic Acids, New York, Wiley.
93. Gerber, P. R. & Müller, K. (1995) J. Comput.-Aid. Mol Design 9, 251-268.