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Volumn 125, Issue 30, 2003, Pages 9035-9037

Secondary structural preferences of 2,2-disubstituted pyrrolidine-4-carboxylic acid oligomers: β-peptide foldamers that cannot form internal hydrogen bonds

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CARBOXYLIC ACID DERIVATIVE; OLIGOMER; PEPTIDE; PYRROLIDINE 4 CARBOXYLIC ACID; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0041866613     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034561c     Document Type: Article
Times cited : (65)

References (34)
  • 18
    • 0033518059 scopus 로고    scopus 로고
    • Huck, B. R.; Langenhan, J. M.; Gellman, S. H. Org. Lett. 1999, 1, 1717. Computational analysis of these systems: Chandrasekhar, J.; Saunders, M.; Jorgensen, W. L. J. Comput. Chem. 2001, 22, 1646.
    • (1999) Org. Lett. , vol.1 , pp. 1717
    • Huck, B.R.1    Langenhan, J.M.2    Gellman, S.H.3
  • 23
    • 0344765393 scopus 로고
    • Loffet, A., Ed.; Editions de l'Universite de Bruxelles: Brussels
    • (b) Rothe, M.; Rott, H.; Mazanek, J. Peptides; Loffet, A., Ed.; Editions de l'Universite de Bruxelles: Brussels, 1976; p 309.
    • (1976) Peptides , pp. 309
    • Rothe, M.1    Rott, H.2    Mazanek, J.3
  • 26
    • 0041371714 scopus 로고    scopus 로고
    • Ph.D. Thesis University of Wisconsin - Madison
    • Huck, B. R. Ph.D. Thesis, University of Wisconsin - Madison, 2002.
    • (2002)
    • Huck, B.R.1
  • 27
    • 0037139577 scopus 로고    scopus 로고
    • and references therein
    • For related efforts to bias rotamer preferences in Xaa-Pro linkages, see: Halab, L.; Lubell, W. D. J. Am. Chem. Soc. 2002, 124, 2474 and references therein.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 2474
    • Halab, L.1    Lubell, W.D.2
  • 33
    • 0041872461 scopus 로고    scopus 로고
    • note
    • Restrained simulated annealing was performed using the Merck molecular force field as implemented in Sybyl. Initial structures were taken from DYANA simulations. NOE derived restraints were included using a flat well potential (range constraints in Sybyl). Constraints of 0-3, 0-4, 0-5 Å plus corrections for pseudo atoms were employed for strong, medium, and weak NOEs, respectively. The molecules were equilibrated for 2 ps at 1000 K and cooled linearly to 200 K over 10 ps with 0.5 fs time steps. The resulting structure was used as the input for the following annealing cycle. Typically, 10-20 cycles were run. A constant dielectric of 9.0 was employed to simulate dichloromethane. Final structures were minimized without constraints and represented local minima.


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