A novel peptide fold: A repeating βII' turn secondary structure [4]

Journal of the American Chemical Society

Volumn 122, Issue 20, 2000, Pages 4986-4987

  Madalengoitia, Jose S ^a  

^a UNIVERSITY OF VERMONT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CADMIUM; PEPTIDE;

HYDROGEN BOND; LETTER; NUCLEAR OVERHAUSER EFFECT; PROTEIN CONFORMATION; PROTEIN FOLDING; PROTEIN SECONDARY STRUCTURE;

EID: 0034709436     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993909u     Document Type: Letter

References (20)

1. For examples of secondary structure studies, see: (a) Tsang, K. Y.; Diaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. (b) Diaz, H.; Espina, J. R.; Kelly, J. W. J. Am. Chem. Soc. 1992, 114, 8316. (c) Seebach, D.; Overhand, M.; Kuhnle, F. N. M.; Martinoni; B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913. (d) Seebach, D.; Ciceri, P. E.; Overhand, M.; Jaun, B.; Rigo, D.; Obere, L.; Hommel, U.; Amstutz, R.; Widmer, H. Helv. Chim. Acta 1996 79, 2043. (e) Appella, D. H.; Christianson, L. A.; Klein, D.; Powell, D. R.; Huang, X.; Barchi, J. J.; Gellman, S. H. Nature 1997, 387, 381. (f) Gung, B. W.; Zou, D.; Stalcup, A. M.; Cottrell, C. E. J. Org. Chem. 1999, 64, 2176. (g) Hanessian, S.; Luo, X.; Schaum, R.; Michnick, S. J. Am. Chem. Soc. 1998, 120, 8569. (h) Nowick, J. S.; Pairish, M.; Lee, I. Q.; Holmes, D. L.; Ziller, J. W. J. Am. Chem. Soc. 1997, 119, 5413. (i) Austin, R. E.; Maplestone, R. A.; Sefler, A. M.; Liu, K.; Hruzewicz, W. N.; Liu, C. W.; Cho, H. S.; Wemmer, D. E.; Bartlett, P. A. J. Am. Chem. Soc. 1997, 119, 6461.
2. For examples of secondary structure studies, see: (a) Tsang, K. Y.; Diaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. (b) Diaz, H.; Espina, J. R.; Kelly, J. W. J. Am. Chem. Soc. 1992, 114, 8316. (c) Seebach, D.; Overhand, M.; Kuhnle, F. N. M.; Martinoni; B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913. (d) Seebach, D.; Ciceri, P. E.; Overhand, M.; Jaun, B.; Rigo, D.; Obere, L.; Hommel, U.; Amstutz, R.; Widmer, H. Helv. Chim. Acta 1996 79, 2043. (e) Appella, D. H.; Christianson, L. A.; Klein, D.; Powell, D. R.; Huang, X.; Barchi, J. J.; Gellman, S. H. Nature 1997, 387, 381. (f) Gung, B. W.; Zou, D.; Stalcup, A. M.; Cottrell, C. E. J. Org. Chem. 1999, 64, 2176. (g) Hanessian, S.; Luo, X.; Schaum, R.; Michnick, S. J. Am. Chem. Soc. 1998, 120, 8569. (h) Nowick, J. S.; Pairish, M.; Lee, I. Q.; Holmes, D. L.; Ziller, J. W. J. Am. Chem. Soc. 1997, 119, 5413. (i) Austin, R. E.; Maplestone, R. A.; Sefler, A. M.; Liu, K.; Hruzewicz, W. N.; Liu, C. W.; Cho, H. S.; Wemmer, D. E.; Bartlett, P. A. J. Am. Chem. Soc. 1997, 119, 6461.
3. For examples of secondary structure studies, see: (a) Tsang, K. Y.; Diaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. (b) Diaz, H.; Espina, J. R.; Kelly, J. W. J. Am. Chem. Soc. 1992, 114, 8316. (c) Seebach, D.; Overhand, M.; Kuhnle, F. N. M.; Martinoni; B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913. (d) Seebach, D.; Ciceri, P. E.; Overhand, M.; Jaun, B.; Rigo, D.; Obere, L.; Hommel, U.; Amstutz, R.; Widmer, H. Helv. Chim. Acta 1996 79, 2043. (e) Appella, D. H.; Christianson, L. A.; Klein, D.; Powell, D. R.; Huang, X.; Barchi, J. J.; Gellman, S. H. Nature 1997, 387, 381. (f) Gung, B. W.; Zou, D.; Stalcup, A. M.; Cottrell, C. E. J. Org. Chem. 1999, 64, 2176. (g) Hanessian, S.; Luo, X.; Schaum, R.; Michnick, S. J. Am. Chem. Soc. 1998, 120, 8569. (h) Nowick, J. S.; Pairish, M.; Lee, I. Q.; Holmes, D. L.; Ziller, J. W. J. Am. Chem. Soc. 1997, 119, 5413. (i) Austin, R. E.; Maplestone, R. A.; Sefler, A. M.; Liu, K.; Hruzewicz, W. N.; Liu, C. W.; Cho, H. S.; Wemmer, D. E.; Bartlett, P. A. J. Am. Chem. Soc. 1997, 119, 6461.
4. For examples of secondary structure studies, see: (a) Tsang, K. Y.; Diaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. (b) Diaz, H.; Espina, J. R.; Kelly, J. W. J. Am. Chem. Soc. 1992, 114, 8316. (c) Seebach, D.; Overhand, M.; Kuhnle, F. N. M.; Martinoni; B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913. (d) Seebach, D.; Ciceri, P. E.; Overhand, M.; Jaun, B.; Rigo, D.; Obere, L.; Hommel, U.; Amstutz, R.; Widmer, H. Helv. Chim. Acta 1996 79, 2043. (e) Appella, D. H.; Christianson, L. A.; Klein, D.; Powell, D. R.; Huang, X.; Barchi, J. J.; Gellman, S. H. Nature 1997, 387, 381. (f) Gung, B. W.; Zou, D.; Stalcup, A. M.; Cottrell, C. E. J. Org. Chem. 1999, 64, 2176. (g) Hanessian, S.; Luo, X.; Schaum, R.; Michnick, S. J. Am. Chem. Soc. 1998, 120, 8569. (h) Nowick, J. S.; Pairish, M.; Lee, I. Q.; Holmes, D. L.; Ziller, J. W. J. Am. Chem. Soc. 1997, 119, 5413. (i) Austin, R. E.; Maplestone, R. A.; Sefler, A. M.; Liu, K.; Hruzewicz, W. N.; Liu, C. W.; Cho, H. S.; Wemmer, D. E.; Bartlett, P. A. J. Am. Chem. Soc. 1997, 119, 6461.
5. For examples of secondary structure studies, see: (a) Tsang, K. Y.; Diaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. (b) Diaz, H.; Espina, J. R.; Kelly, J. W. J. Am. Chem. Soc. 1992, 114, 8316. (c) Seebach, D.; Overhand, M.; Kuhnle, F. N. M.; Martinoni; B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913. (d) Seebach, D.; Ciceri, P. E.; Overhand, M.; Jaun, B.; Rigo, D.; Obere, L.; Hommel, U.; Amstutz, R.; Widmer, H. Helv. Chim. Acta 1996 79, 2043. (e) Appella, D. H.; Christianson, L. A.; Klein, D.; Powell, D. R.; Huang, X.; Barchi, J. J.; Gellman, S. H. Nature 1997, 387, 381. (f) Gung, B. W.; Zou, D.; Stalcup, A. M.; Cottrell, C. E. J. Org. Chem. 1999, 64, 2176. (g) Hanessian, S.; Luo, X.; Schaum, R.; Michnick, S. J. Am. Chem. Soc. 1998, 120, 8569. (h) Nowick, J. S.; Pairish, M.; Lee, I. Q.; Holmes, D. L.; Ziller, J. W. J. Am. Chem. Soc. 1997, 119, 5413. (i) Austin, R. E.; Maplestone, R. A.; Sefler, A. M.; Liu, K.; Hruzewicz, W. N.; Liu, C. W.; Cho, H. S.; Wemmer, D. E.; Bartlett, P. A. J. Am. Chem. Soc. 1997, 119, 6461.
6. For examples of secondary structure studies, see: (a) Tsang, K. Y.; Diaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. (b) Diaz, H.; Espina, J. R.; Kelly, J. W. J. Am. Chem. Soc. 1992, 114, 8316. (c) Seebach, D.; Overhand, M.; Kuhnle, F. N. M.; Martinoni; B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913. (d) Seebach, D.; Ciceri, P. E.; Overhand, M.; Jaun, B.; Rigo, D.; Obere, L.; Hommel, U.; Amstutz, R.; Widmer, H. Helv. Chim. Acta 1996 79, 2043. (e) Appella, D. H.; Christianson, L. A.; Klein, D.; Powell, D. R.; Huang, X.; Barchi, J. J.; Gellman, S. H. Nature 1997, 387, 381. (f) Gung, B. W.; Zou, D.; Stalcup, A. M.; Cottrell, C. E. J. Org. Chem. 1999, 64, 2176. (g) Hanessian, S.; Luo, X.; Schaum, R.; Michnick, S. J. Am. Chem. Soc. 1998, 120, 8569. (h) Nowick, J. S.; Pairish, M.; Lee, I. Q.; Holmes, D. L.; Ziller, J. W. J. Am. Chem. Soc. 1997, 119, 5413. (i) Austin, R. E.; Maplestone, R. A.; Sefler, A. M.; Liu, K.; Hruzewicz, W. N.; Liu, C. W.; Cho, H. S.; Wemmer, D. E.; Bartlett, P. A. J. Am. Chem. Soc. 1997, 119, 6461.
7. For examples of secondary structure studies, see: (a) Tsang, K. Y.; Diaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. (b) Diaz, H.; Espina, J. R.; Kelly, J. W. J. Am. Chem. Soc. 1992, 114, 8316. (c) Seebach, D.; Overhand, M.; Kuhnle, F. N. M.; Martinoni; B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913. (d) Seebach, D.; Ciceri, P. E.; Overhand, M.; Jaun, B.; Rigo, D.; Obere, L.; Hommel, U.; Amstutz, R.; Widmer, H. Helv. Chim. Acta 1996 79, 2043. (e) Appella, D. H.; Christianson, L. A.; Klein, D.; Powell, D. R.; Huang, X.; Barchi, J. J.; Gellman, S. H. Nature 1997, 387, 381. (f) Gung, B. W.; Zou, D.; Stalcup, A. M.; Cottrell, C. E. J. Org. Chem. 1999, 64, 2176. (g) Hanessian, S.; Luo, X.; Schaum, R.; Michnick, S. J. Am. Chem. Soc. 1998, 120, 8569. (h) Nowick, J. S.; Pairish, M.; Lee, I. Q.; Holmes, D. L.; Ziller, J. W. J. Am. Chem. Soc. 1997, 119, 5413. (i) Austin, R. E.; Maplestone, R. A.; Sefler, A. M.; Liu, K.; Hruzewicz, W. N.; Liu, C. W.; Cho, H. S.; Wemmer, D. E.; Bartlett, P. A. J. Am. Chem. Soc. 1997, 119, 6461.
8. For examples of secondary structure studies, see: (a) Tsang, K. Y.; Diaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. (b) Diaz, H.; Espina, J. R.; Kelly, J. W. J. Am. Chem. Soc. 1992, 114, 8316. (c) Seebach, D.; Overhand, M.; Kuhnle, F. N. M.; Martinoni; B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913. (d) Seebach, D.; Ciceri, P. E.; Overhand, M.; Jaun, B.; Rigo, D.; Obere, L.; Hommel, U.; Amstutz, R.; Widmer, H. Helv. Chim. Acta 1996 79, 2043. (e) Appella, D. H.; Christianson, L. A.; Klein, D.; Powell, D. R.; Huang, X.; Barchi, J. J.; Gellman, S. H. Nature 1997, 387, 381. (f) Gung, B. W.; Zou, D.; Stalcup, A. M.; Cottrell, C. E. J. Org. Chem. 1999, 64, 2176. (g) Hanessian, S.; Luo, X.; Schaum, R.; Michnick, S. J. Am. Chem. Soc. 1998, 120, 8569. (h) Nowick, J. S.; Pairish, M.; Lee, I. Q.; Holmes, D. L.; Ziller, J. W. J. Am. Chem. Soc. 1997, 119, 5413. (i) Austin, R. E.; Maplestone, R. A.; Sefler, A. M.; Liu, K.; Hruzewicz, W. N.; Liu, C. W.; Cho, H. S.; Wemmer, D. E.; Bartlett, P. A. J. Am. Chem. Soc. 1997, 119, 6461.
9. For examples of secondary structure studies, see: (a) Tsang, K. Y.; Diaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988. (b) Diaz, H.; Espina, J. R.; Kelly, J. W. J. Am. Chem. Soc. 1992, 114, 8316. (c) Seebach, D.; Overhand, M.; Kuhnle, F. N. M.; Martinoni; B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913. (d) Seebach, D.; Ciceri, P. E.; Overhand, M.; Jaun, B.; Rigo, D.; Obere, L.; Hommel, U.; Amstutz, R.; Widmer, H. Helv. Chim. Acta 1996 79, 2043. (e) Appella, D. H.; Christianson, L. A.; Klein, D.; Powell, D. R.; Huang, X.; Barchi, J. J.; Gellman, S. H. Nature 1997, 387, 381. (f) Gung, B. W.; Zou, D.; Stalcup, A. M.; Cottrell, C. E. J. Org. Chem. 1999, 64, 2176. (g) Hanessian, S.; Luo, X.; Schaum, R.; Michnick, S. J. Am. Chem. Soc. 1998, 120, 8569. (h) Nowick, J. S.; Pairish, M.; Lee, I. Q.; Holmes, D. L.; Ziller, J. W. J. Am. Chem. Soc. 1997, 119, 5413. (i) Austin, R. E.; Maplestone, R. A.; Sefler, A. M.; Liu, K.; Hruzewicz, W. N.; Liu, C. W.; Cho, H. S.; Wemmer, D. E.; Bartlett, P. A. J. Am. Chem. Soc. 1997, 119, 6461.
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14. For examples of the use of pseudo A(1,3)-strain in the design of conformationally constrained peptides see: (a) Zhang, R.; Brownewell, F.; Madalengoitia, J. S. J. Am. Chem. Soc. 1998, 120, 3894. (b) Zhang, R.; Madalengoitia, J. S. J. Org. Chem. 1999, 64, 330.
15. For examples of the use of pseudo A(1,3)-strain in the design of conformationally constrained peptides see: (a) Zhang, R.; Brownewell, F.; Madalengoitia, J. S. J. Am. Chem. Soc. 1998, 120, 3894. (b) Zhang, R.; Madalengoitia, J. S. J. Org. Chem. 1999, 64, 330.
16. As a compromise between spin diffusion, zero quantum coherence, and signal-to-noise ratio a 400 ms mixing time was utilized in all NOESY experiments. More details are included in the Supporting Information.
17. δ2(Pro2) distances are 2.53 and 3.23 Å respectively (ref 2d). In as much as minimal spin diffusion is assumed in the present study, the analogous calculated distances for peptides in this study consistently ranged 2.8-3.2 Å.
18. Liang, G.-B.; Rito, C. J.; Gellman, S. H. Biopolymers 1992, 32, 293.
19. α(Pro) NOE exhibited by 7 is also exhibited in every potential turn unit in the multiple turn peptides.
20. The reviewers have pointed out that this statement is puzzling considering that cooperatively should stabilize the longer structure. The author agrees that this is a curious statement: however, it is not clear at this juncture whether this fold is cooperative. Evidence for cooperativity comes from the increased resistance to solvent perturbation some NH resonances exhibit as the number of turns increases. In addition, cisltrans amide bond isomerism which is quite evident in the one turn unit 3 (∼10% cis) is less evident in the multiple turn peptides also suggesting cooperativity. However, some arguments could also be made that H-bond cooperativity may not necessarily play a dominant role. For example, Seebach has proposed that H-bonding in β-peptide helices is noncooperative and that ethane staggering (e.g., minimization of steric interactions) is the predominant stabilizing force. Considering minimization of pseudo A(1,3)-strain (a steric interaction) contributes significantly to the stability of a βII′ turn and considering that the formation of a hydrogen bond in one turn unit does not aid in bringing into closer proximity the groups which hydrogen bond in the adjacent turn unit, it may be that H-bond cooperativety is not a major stabilizing force. Gademann, K.; Jaun, B.; Seebach, D.; Perozzo, R.; Scapozza, L.; Folkers, G. Helv. Chim. Acta 1999, 82, 1.