Effects of alternative side chain pairings and reverse turn sequences on antiparallel sheet structure in β-peptide hairpins

Organic Letters

Volumn 6, Issue 6, 2004, Pages 937-940

  Langenhan, Joseph M ^a   Gellman, Samuel H ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

METHANOL; PEPTIDE DERIVATIVE; WATER;

ARTICLE; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE; PROTEIN FOLDING;

MAGNETIC RESONANCE SPECTROSCOPY; METHANOL; PROTEIN FOLDING; PROTEIN STRUCTURE, SECONDARY; PROTEINS; WATER;

EID: 1642569138     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0364430     Document Type: Article

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16. Systems containing strand mimics: (a) Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5081. (b) Nowick, J. S. Acc. Chem. Res. 1999, 32, 287. (c) Nowick, J. S.; Lam, K. S.; Khasanova, T. V.; Kemnitzer, W. E.; Maitra, S.; Mee, H. T.; Lui, R. J. Am. Chem. Soc. 2002, 124, 4972 and references therein. (d) Langenhan, J. M.; Fisk, J. D.; Gellman, S. H. Org. Lett. 2001, 3, 2559. (e) Karle, I. L.; Gopi, H. N.; Balaram, P. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5160 and references therein. (f) Yang, X.; Merinovic, S.; Smith, R. D.; Gong, B. J. Am. Chem. Soc. 2003, 125, 9932. (g) Zeng, H.; Yang, X.; Flowers, R. A., II.; Gong, B. J. Am. Chem. Soc. 2002, 124, 2903.
17. Systems containing strand mimics: (a) Kemp, D. S.; Bowen, B. R. Tetrahedron Lett. 1988, 29, 5081. (b) Nowick, J. S. Acc. Chem. Res. 1999, 32, 287. (c) Nowick, J. S.; Lam, K. S.; Khasanova, T. V.; Kemnitzer, W. E.; Maitra, S.; Mee, H. T.; Lui, R. J. Am. Chem. Soc. 2002, 124, 4972 and references therein. (d) Langenhan, J. M.; Fisk, J. D.; Gellman, S. H. Org. Lett. 2001, 3, 2559. (e) Karle, I. L.; Gopi, H. N.; Balaram, P. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5160 and references therein. (f) Yang, X.; Merinovic, S.; Smith, R. D.; Gong, B. J. Am. Chem. Soc. 2003, 125, 9932. (g) Zeng, H.; Yang, X.; Flowers, R. A., II.; Gong, B. J. Am. Chem. Soc. 2002, 124, 2903.
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29. Espinosa, J. F.; Gellman, S. H. Angew. Chem., Int. Ed. 2000, 39, 2330. Stanger, H. E.; Syud, F. A.; Espinosa, J. F.; Giriat, I.; Muir, T.; Gellman, S. H. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 12015. One computational study suggests that parallel β-peptide sheet formation is not cooperative along the strand direction. However, this study was performed in the gas phase, and it is not clear whether antiparallel β-peptide sheets behave similarly to parallel β-peptide sheets. See: Lin, J. Q.; Luo, S.-W.; Wu, Y.-D. J. Comput. Chem. 2002, 23, 1551.
30. Espinosa, J. F.; Gellman, S. H. Angew. Chem., Int. Ed. 2000, 39, 2330. Stanger, H. E.; Syud, F. A.; Espinosa, J. F.; Giriat, I.; Muir, T.; Gellman, S. H. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 12015. One computational study suggests that parallel β-peptide sheet formation is not cooperative along the strand direction. However, this study was performed in the gas phase, and it is not clear whether antiparallel β-peptide sheets behave similarly to parallel β-peptide sheets. See: Lin, J. Q.; Luo, S.-W.; Wu, Y.-D. J. Comput. Chem. 2002, 23, 1551.
31. Langenhan, J. M. Ph.D. Thesis, University of Wisconsin-Madison, 2003.