Comparisons of the conformational biases imposed by trans-2,3-methanomethionine and α-methylmethionine

Biopolymers - Nucleic Acid Sciences Section

Volumn 42, Issue 4, 1997, Pages 439-453

  Burgess, Kevin ^a   Li, Wen ^a   Lim, Dongyeol ^a   Moye Sherman, Destardi ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

A methylmethionine; Cyclopropyl amino acids; Lrans 2,3 inethanomethionine; Peptidomimetics; Stereoisomers

Indexed keywords

AMINO ACIDS; COMPUTER SIMULATION; CONFORMATIONS; MOLECULAR STRUCTURE; MOLECULES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTONS;

CYCLOPROPYL AMINO ACIDS; METHANOMETHIONINE; METHYLMETHIONINE; OVERHAUSER EFFECT; PEPTIDOMIMETICS; STEREOISOMERS;

POLYPEPTIDES;

METHIONINE DERIVATIVE; PHENYLALANYLMETHIONYLARGINYLPHENYLALANINAMIDE;

ARTICLE; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; PROTEIN CONFORMATION; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ANALYSIS;

FMRFAMIDE; METHIONINE; NEUROPEPTIDES; OLIGOPEPTIDES; PROTEIN CONFORMATION;

EID: 0031555017     PISSN: 00063525     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-0282(19971005)42:4<439::AID-BIP7<3.0.CO;2-R     Document Type: Article

References (50)

1. Burgess, K. & Ho, K.-K. (1992) J. Org. Cliem. 57, 5931.
2. Burgess, K. & Ho, K.-K. (1992) Tetrahed. Lett. 33, 5677.
3. Burgess, K., Ho, K.-K. & Ke, C.-Y. (1993) J. Org. Chem. 58, 3767.
4. Burgess, K., Lim, D., Ho, K.-K. & Ke, C.-Y. ( 1994) J. Org. Chem. 59, 2179.
5. Burgess, K., Ho, K.-K. & Moye-Sherman, D. (1994) SYNLETT 8, 575.
6. Burgess, K., Ho, K.-K. & Pettitt, B. M. (1995) J. Am. Chem. Soc. 117, 54.
7. Burgess, K., Ho, K.-K. & Pal, B. (1995) J. Am. Chem. Soc. 117, 3808.
8. Burgess, K., Ho, K.-K. & Pettitt, B. M. (1994) J. Am. Chem. Soc. 116, 799.
9. Burgess, K. & Li, W. (1995) Tetrahed. Lett. 36, 2725.
10. Burgess, K. & Lim, D. Y. (1995) Tetrahed. Lett. 36, 7815.
11. Malin, D. H., Payza, K., Lake, J. R., Corriere, L. S., Benson, T. M., Smith, D. A., Baugher, R. K., Ho, K.-K. & Burgess, K. (1993) Peptides 14, 47.
12. Malin, D. H., Lake, J. R., Ho, K.-K., Corriere, L. S., Garber, T. M., Waller, M., Benson, T., Smith, D. A., Luu, T.-A. & Burgess, K. (1993) Peptides 14, 731.
13. Malin, D.H., Lake, J. R., Jones, J. A., McDermitt, L. S., Smith, D. A., Witherspoon, W. E., Schumann, M. D., Payza, K., Ho, K.-K. & Burgess, K. (1996) Peptides 17, 83.
14. Beck, A. K. & Seebach, D. (1988) Chimia 42, 142.
15. Marshall, G. R. ( 1971 ) Intra-Sci. Chem. Rep. 5,305.
16. Marshall, G. R. & Bosshard, H.E. (1972) Circul. Res., Siippl. II30, 143.
17. Turk, J., Panse, G. T. & Marshall, G. R. (1975) J. Org. Chem. 40, 953.
18. Burgess, A.W. & Leach, S. J. (1973) Biopolymers 12, 2599.
19. Toniolo, C., Bonora, G. M., Bavoso, A., Benedetti, E., Blasio, B. D., Pavone, V. & Pedone, C. (1983) Biopolymers 22, 205.
20. Prasac, B. V. V. & Balaram, P. (1984) CRC 16,307.
21. Toniolo, C. & Benedetti, E. (1991) Macromolecules 24, 4004.
22. Augspurger, J. D., Bindra, V. A., Scheraga, H. A. & Kuki, A. (1995) Biochemistry 34, 2566.
23. Zhang, L. & Hermans, J. (1994) J. Am. Chem. Soc. 116, 11915.
24. Roey, P. V., Smith, G. D., Balasubramanian, T. M. & Marshall, G. R. (1981) Acta Cryst. B37, 1785.
25. Marshall, G. R-, Clark, J. D., James B. Dunbar, J., Smith, G. D., Zabrocki, J., Redlinski, A. S. & Leplavvy, M. T. (1988) Int. J. Peptide Protein Res. 32, 544.
26. Altmann, E., Altmann, K.-H., Nebel, K. & Mutter, M. (1988) Int. J. Peptide Protein Res. 32, 344.
27. Toniolo, C., Crisma, M., Formaggio, F., Valle, G., Cavicchioni, G., Precigoux, G., Aubry, A. & Kamphuis, J. (1993) Biopolymers 33, 1061.
28. Aubry, A., Bayeul, D., Precigoux, G., Pantano, M., Formaggio, F., Crisma, M., Toniolo, C., Boesten, W. H. J. & Schoemaker, H. E. (1994) J. Chem. Soc. Perkin Trans. 2 525.
29. Formaggio, F., Crisma, M., Toniolo, C., Benedetti, E., Blasio, B. D., Saviano, M., Galdiero, S., Kamphuis, J. & Santini, A. (1995) J. Peptide Sci. l, 396.
30. Toniolo, C., Crisma, M., Bonora, G. M., Klajc, B., Lelj, F., Grimaldi, P., Rosa, A., Polinelli, S., Boesten, W. H. J., Meijer, E. M., Schoemaker, H. E. & Kamphuis, J. ( 1991 ) Int. J. Peptide Protein Res. 38, 242.
31. Valle, G., Crisma, M., Toniolo, C., Polinelli, S., Boesten, W. H. J., Schoemaker, H. E., Meijer, E. M. & Kamphuis, J. ( 1991 ) Int. J. Peptide Protein Res. 37, 521.
32. Formaggio, F., Pantano, M., Valle, G., Crisma, M., Bonora, G. M., Mammi, S., Peggion, E., Toniolo, C., Boesten, W. H. J., Schoemaker, H. E. & Kamphuis, J. (1993) Macromolecules 26, 1848.
33. Toniolo, C., Pantano, M., Formaggio, F., Crisma, M., Bonora, M., Aubry, A., Bayeul, D., Dautant, A., Boesten, W. H. J., Schoemaker, H. E. & Kamphuis, J. (1994) Int. J. Biol. Macromol. 16, 7.
34. Bisang, C., Weber, C., Inglis, J., Schiffer, C. A., Gunsteren, W. F. v., Jelesarov, L, Bosshard, H. R. & Robinson, J. A. ( 1995) J. Am. Chem. Soc. 117,7904.
35. Valle, G., Crisma, M., Toniolo, C., Beisswenger, R., Rieker, A. & Jung, G. (1989) J. Am. Chem. Soc. Ill, 6828.
36. Stewart, J. M. & Young, J. D. ( 1984) in Solid Phase Peptide Synthesis, Pierce Chemical Company, Rockford, IL.
37. Rink, H. (1987) Tetrahed. Lett. 28, 3787.
38. Pettitt, B. M., Matsunaga, T., Al-Obeidi, F., Gehrig, C., Hruby, V.J. & Karplus, M. (1991) J. Biophys. Soc. 60, 1540.
39. O'Connor, S. D., Smith, P. E., Al-Obeidi, F. & Pettitt, B. M. (1992) J. Med. Chem. 35, 2870.
40. Bax, A. & Davis, D. G. (1985) J. Mag. Reson. 63, 207.
41. Wuthrich, K. (1986) in NMR of Proteins and Nucleic Acids, Wiley, New York.
42. Ohnishi, M. & Urry, D.W. (1969) Biochem. Biophys. Res. Commun. 36, 194.
43. Kopple, K. D., Ohnishi, M. & Go, A. (1969) J. Am. Chem. Soc. 91, 4264.
44. Felix, A. M., Wang, C.-T., Heimer, E. P. & Foumier, A. (1988) Int. J. Peptide Protein Res. 31, 231.
45. Brooks, B., Bruccoleri, R., Olafson, H., States, D., Swaminathan, S. & Karplus, M. (1983) J. Compiit. Chem. 4, 187.
46. Varughese, K. L, Srinivasan, A. R. & Stammer, C. H. (1985) Int. J. Peptide Protein Res. 26, 242.
47. Baldwin, J. E., Adlington, R. M., Rawlings, B. J. & Jones, R. H. ( 1985) Tetrahed. Lett. 26, 485.
48. Piantini, U., Sorensen, O. W. & Ernst, R. R. (1982) J. Am. Chem. Soc. 104, 6800.
49. Bothner-By, A. A., Stephen, R. L., Lee, J., Warren, C. D. & Jeanloz, R. W. (1984) J. Am. Chem. Soc. 106,811.
50. Neuhaus, D. (1986) J. Mag. Reson. 68, 568.1.