An artificial β-sheet comprising a molecular scaffold, a β-strand mimic, and a peptide strand

Journal of the American Chemical Society

Volumn 118, Issue 11, 1996, Pages 2764-2765

  Nowick, James S ^a   Holmes, Darren L ^a   Mackin, Gilbert ^a   Noronha, Glenn ^a   Shaka, A J ^a   Smith, Eric M ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; MODEL; NUCLEAR MAGNETIC RESONANCE; PROTEIN STRUCTURE;

EID: 0029670181     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953334a     Document Type: Article

References (20)

1. (a) Mutter, M.; Altmann, E.; Altmann, K.-H.; Hersperger, R.; Koziej, P.; Nebel, K.; Tuchscherer, G.; Vuilleumier, S.; Gremlich, H.-U.; Müller, K. Helv. Chim. Acta 1988, 71, 835.
2. (b) Kemp, D. S.; Bowen, B. R.; Muendel, C. C. J. Org. Chem. 1990, 55, 4650 and references contained therein.
3. (c) Wagner, G ; Feigel M. Tetrahedron 1993, 49, 10831 and references contained therein.
4. (d) Brandmeier, V.; Sauer, W. H. B.; Feigel, M. Helv. Chim. Acta 1994, 77, 70 and references contained therein.
5. (e) Tsang, K. Y ; Diaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988 and references contained therein.
6. (f) Smith, A B., III; Guzman, M. C.; Sprengeler, P. A.; Keenan, T. P.; Holcomb, R C.; Wood, J. L ; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1994, 116, 9947 and references contained therein.
7. (g) Winningham, M J.; Sogah, D. Y. J. Am. Chem. Soc 1994, 116, 11173
8. (h) LaBrenz, S. R.; Kelly, J W. J. Am Chem. Soc. 1995, 117, 1655.
9. (i) Schneider, J. P.; Kelly, J. W. J Am. Chem. Soc. 1995, 117, 2533.
10. (j) Gardner, R. R ; Liang, G.-B.; Gellman, S. H. J. Am. Chem. Soc. 1995, 117, 3280.
11. (k) Kemp, D. S.; Li, Z. Q. Tetrahedron Lett. 1995, 36, 4175.
12. Kemp, D. S ; Li, Z. Q. Tetrahedron Lett. 1995, 36, 4179.
13. (a) Nowick, J S.; Powell, N. A , Martinez, E J.; Smith, E. M.; Noronha, G. J. Org. Chem. 1992, 57, 3763.
14. (b) Nowick, J. S , Abdi, M.; Bellamo, K. A., Love, J. A., Martinez, E. J.; Noronha, G ; Smith, E M.; Ziller, J. W J. Am. Chem. Soc 1995, 117, 89.
15. (c) Nowick, J S ; Smith, E. M., Noronha, G. J. Org. Chem. 1995, 60, 7386.
16. (d) Nowick, J. S.; Mahrus, S., Smith, E. M.; Ziller, J. W J. Am Chem Soc. 1996, 118, 1066
17. AX = 6.1 Hz, 1 H, 10), 3.48 (dt. J = 14.1, 6.3 Hz, 1 H, 11), 3.56 (dt, J = 14.0, 6.2 Hz, 1 H, 12), 3.62 (appar ddd, J = 14 6, 9.2, 4.3 Hz, 1 H, 13), 3.71 (appar ddd, J = 15.2, 9.8, 5.3 Hz, 1 H, 14), 3.76 (appar ddd, J = 15.1, 10.0, 5.1 Hz, 1 H, 15), 3.86 (appar ddd, J = 13.6, 9.5, 4.9 Hz, 1 H, 16), 3 95 (s, 3 H, 17), 4.38 (ddd, J = 11.8, 8.9. 3.4 Hz, 1 H, 18), 4.94 (td, J = 9.2, 6.2 Hz, 1 H, 19), 5.00 (d, J = 8.6 Hz, 1 H, 20), 5.51 (appar q, J = 4.3 Hz, 1 H, 21), 6.92 (d, J = 9.1 Hz, 1 H, 22), 7.14 (d, J = 7.7 Hz, 2 H, 23), 7.27-7.31 (m, 5 H, 24), 7.38 (t. J = 7.4 Hz, 1 H, 25), 7.45 (t. J = 7.6 Hz, 2 H, 26), 8.07 (appar q. J = 4.6 Hz, 1 H, 27), 8.13 (d, J = 8.9 Hz, 1 H, 28), 8.36 (dd. J = 8.9, 2.8 Hz, 1 H, 29), 8.51 (d, J = 3 0 Hz, 1 H, 30), 9.94 (s, 1 H, 31).
18. Other smaller chemical shift differences are also observed. Compound 4: leucine methylamide NH (21). 5.45 ppm: phenylalanine NH (20), 5 02 ppm: "upper" methylamide NH (27), 8.11 ppm. Compound 5: methylamide NH, 7.92 ppm. Compound 6: phenylalanine NH, 4.44 ppm; leucine methylamide NH, 6 73 ppm. We attribute the difference in chemical shifts of the leucine methylamide groups to anisotropic effects of the aromatic rings of 4 and to the propensity of 6 to adopt a hydrogen-bonded β-turn conformation, in which the methylamide NH is hydrogen bonded to the urea carbonyl group.
19. Stott, K.; Stonehouse, J.; Keeler, J.; Hwang, T.-L.; Shaka, A. J. J. Am Chem. Soc. 1995, 117, 4199.
20. DPFGSE NOE experiments were performed using 0.5 s mixing times. NOEs are reported in parentheses as percentage enhancement relative to area of the irradiated peak in the DPFSGE NOE spectrum and are normalized for the number of protons involved. (These values are not steady-state NOEs and only indicate the relative enhancements of resonances within a given experiment.) NOEs of 0.2% or greater are reported. Percentage enhancements of resonances 4 and 5 are approximate because these resonances overlap. Percentage enhancements of resonances 8 and 10 are approximate because these resonances overlap. Irradiation of methyl group 1 enhances resonances 2 (1.1), 3 (2.5), 4 (2.7), 5 (4.4), 13 (0.2), 18 (0.4), 29 (0.2), 30 (0.4), and 31 (0.3). Irradiation of methyl group 2 enhances resonances 1 (1.2), 4 (2.5), 5 (4.5), 13 (0.2), 18 (5.0), and 23 (0.3). Irradiation of proton 3 enhances resonances 1 (0.8), 4 (6.2), 5 (18 1), 18 (0.9), 21 (0.3), 27 (0.3), 28 (2.4), and 30 (0.5). Irradiation of methyl group 6 enhances resonances 9 (0.3), 18 (0 2), 21 (4.7), and 24 (0.4) Irradiation of proton 18 enhances resonances 2 (1.1), 3 (0.5), 4 (0.9), 5 (2.5), 21 (0.9), and 28 (1.3), Irradiation of proton 21 enhances resonances 3 (0.2), 6 (1 7), 9 (0.3), 18 (1.3), 24 (0.3), 28 (3.1), and 30 (0.2). Irradiation of protons 23 enhances resonances 13 (0 4), 14 (0 5), 15 (0.8), 16 (0.7), 19 (0.6), 20 (1 5), 25 (0.5), and 26 (3.2). Irradiation of protons 24 enhances resonances 6 (0.3), 8 (1.7), 10 (2 7), 19 (1 8), 20 (1.0), 21 (0.7), 28 (0.3), and 30 (0.2). Irradiation of proton 30 enhances resonances 3 (0.3), 4 (0.9), 5 (0.3), 19 (1 6), 20 (0.2), 28 (1 9), and 31 (5.2). Irradiation of proton 31 enhances resonances 3 (0.2), 4 (0.7), 13 (5.5), 14 (5.0), 15 (3.7), 16 (3.1), 19 (0.3), 29 (0 8), and 30 (9.9).