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Volumn 129, Issue 17, 2007, Pages 5558-5569

Macrocyclic β-sheet peptides that mimic protein quaternary structure through intermolecular β-sheet interactions

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIC PEPTIDES; HEPTAPEPTIDE SEQUENCES; QUATERNARY STRUCTURE;

EID: 34247884335     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja068511u     Document Type: Article
Times cited : (72)

References (108)
  • 20
    • 0027471542 scopus 로고    scopus 로고
    • For examples of large peptides that fold into larger β-sheet structures, see: (a) Pessi, A, Bianchi, E, Crameri, A, Venturini, S, Tramontano, A, Sollazzo, M. Nature 1993, 362, 367-369
    • For examples of large peptides that fold into larger β-sheet structures, see: (a) Pessi, A.; Bianchi, E.; Crameri, A.; Venturini, S.; Tramontano, A.; Sollazzo, M. Nature 1993, 362, 367-369.
  • 35
  • 56
    • 34247899591 scopus 로고    scopus 로고
    • (b) http://www.igb.uci.edu/servers/icbs/.
  • 59
    • 0342716088 scopus 로고    scopus 로고
    • For other examples of designed cyclic peptides that fold into β-sheet structures, see: a
    • For other examples of designed cyclic peptides that fold into β-sheet structures, see: (a) Spath, J.; Stuart, F.; Jiang, L.; Robinson, J. A. Helv. Chim. Acta 1998, 81, 1726-1738.
    • (1998) Helv. Chim. Acta , vol.81 , pp. 1726-1738
    • Spath, J.1    Stuart, F.2    Jiang, L.3    Robinson, J.A.4
  • 62
    • 0027447199 scopus 로고    scopus 로고
    • Other cyclic peptides containing 54-membered rings (cyclo- octadecapeptides, including naturally occurring θ-defensin, have been previously synthesized and studied. For examples, see ref 19c and (a) Ando, S, Nishikawa, H, Takiguchi, H, Lee, S, Sugihara, G. Biochim. Biophys. Acta. Biomembranes 1993, 1147, 42-49
    • Other cyclic peptides containing 54-membered rings (cyclo- octadecapeptides), including naturally occurring θ-defensin, have been previously synthesized and studied. For examples, see ref 19c and (a) Ando, S.; Nishikawa, H.; Takiguchi, H.; Lee, S.; Sugihara, G. Biochim. Biophys. Acta. Biomembranes 1993, 1147, 42-49.
  • 67
    • 34247880886 scopus 로고    scopus 로고
    • PS-PEG-trityl chloride resin was prepared from PS-PEG-trityl alcohol resin (Novabiochem NovaSyn TGT alcohol resin) by treatment with acetyl chloride, as described in the Novabiochem catalog
    • PS-PEG-trityl chloride resin was prepared from PS-PEG-trityl alcohol resin (Novabiochem NovaSyn TGT alcohol resin) by treatment with acetyl chloride, as described in the Novabiochem catalog.
  • 68
    • 34247864352 scopus 로고    scopus 로고
    • 2O solution.
    • 2O solution.
  • 70
    • 34247878254 scopus 로고    scopus 로고
    • α values (average of 0.05 ppm) than those of peptide 6 (Figure 3). This slight downfield shifting of the peptide 3a monomer suggests a somewhat greater population of β-strand conformer.
    • α values (average of 0.05 ppm) than those of peptide 6 (Figure 3). This slight downfield shifting of the peptide 3a monomer suggests a somewhat greater population of β-strand conformer.
  • 71
    • 34247845026 scopus 로고    scopus 로고
    • NOEs among side chains that might arise from further self-association of the dimers cannot be distinguished from those resulting from folding and dimerization
    • NOEs among side chains that might arise from further self-association of the dimers cannot be distinguished from those resulting from folding and dimerization.
  • 72
    • 0031498272 scopus 로고    scopus 로고
    • For an introduction to PFG NMR, see: a
    • For an introduction to PFG NMR, see: (a) Price, W. S. Concepts Magn. Reson. 1997, 9, 299-336.
    • (1997) Concepts Magn. Reson , vol.9 , pp. 299-336
    • Price, W.S.1
  • 78
    • 34247875169 scopus 로고    scopus 로고
    • Exchange between the monomer and the oligomer occurs relatively slowly, on the time scale of the PFG NMR experiment, and has little effect on the diffusion coefficients observed for either species
    • Exchange between the monomer and the oligomer occurs relatively slowly, on the time scale of the PFG NMR experiment, and has little effect on the diffusion coefficients observed for either species.
  • 87
    • 34247899590 scopus 로고    scopus 로고
    • 2O solution without NaCl. This result indicates that the oligomerization states do not change upon adding NaCl.
    • 2O solution without NaCl. This result indicates that the oligomerization states do not change upon adding NaCl.
  • 90
    • 34247892864 scopus 로고    scopus 로고
    • 3/g according to ref 36b.
    • 3/g according to ref 36b.
  • 91
    • 33744816438 scopus 로고    scopus 로고
    • Scott, D. J, Harding, S. E, Rowe, A. J, Eds, Royal Society of Chemistry: U.K
    • (a) Demeler, B. In Modern Analytical Ultracentrifugation: Techniques and Methods; Scott, D. J., Harding, S. E., Rowe, A. J., Eds.; Royal Society of Chemistry: U.K., 2005; pp 210-229.
    • (2005) Modern Analytical Ultracentrifugation: Techniques and Methods , pp. 210-229
    • Demeler, B.1
  • 92
    • 34247846781 scopus 로고    scopus 로고
    • (b) http://www.ultrascan.uthscsa.edu.
  • 94
    • 24144485161 scopus 로고    scopus 로고
    • Finite element analysis of the data from the 39 μM experiment suggests that this peak corresponds to the monomer. For a description of finite element analysis, see: (a) Cao, W.; Demeler, B. Biophys. J. 2005, 89, 1589-1602.
    • Finite element analysis of the data from the 39 μM experiment suggests that this peak corresponds to the monomer. For a description of finite element analysis, see: (a) Cao, W.; Demeler, B. Biophys. J. 2005, 89, 1589-1602.
  • 97
    • 34247871912 scopus 로고    scopus 로고
    • The UV-absorbance data from the 15 μM samples (g and h) are scaled to fringes and appear relatively shallow because they are plotted on the same scale as the data from the 1.5 and 9 mM experiments.
    • The UV-absorbance data from the 15 μM samples (g and h) are scaled to fringes and appear relatively shallow because they are plotted on the same scale as the data from the 1.5 and 9 mM experiments.
  • 100
    • 34247866991 scopus 로고    scopus 로고
    • The ionization state of the GIu residue in peptides 3b and 3h is not certain, because the studies were done without buffer. Attempts to control the pH with phosphate buffer resulted in precipitation of these peptides.
    • The ionization state of the GIu residue in peptides 3b and 3h is not certain, because the studies were done without buffer. Attempts to control the pH with phosphate buffer resulted in precipitation of these peptides.
  • 101
    • 34247886499 scopus 로고    scopus 로고
    • 2/s, respectively, which are about the same as those values for the monomer and tetramer of peptide 3a. The ratio of these values (0.57) is consistent with tetramer formation.
    • 2/s, respectively, which are about the same as those values for the monomer and tetramer of peptide 3a. The ratio of these values (0.57) is consistent with tetramer formation.
  • 102
    • 34247890609 scopus 로고    scopus 로고
    • 2/s, which is about the same as that of the tetramer of peptide 3a at the same temperature.
    • 2/s, which is about the same as that of the tetramer of peptide 3a at the same temperature.
  • 103
    • 34247862788 scopus 로고    scopus 로고
    • The diffusion coefficients of the oligomers of peptides 3j and 3k are about 0.80-0.85 times that of the tetramer of peptide 3a. The smaller diffusion coefficients of these peptides suggest that peptides 3j and 3k form higher oligomers, such as hexamers or octamers, rather than tetramers. ROESY experiments show that the oligomers of these peptides comprise edge-to-edge dimers. The higher oligomers may be thought of as small micelles in which the hydrophobic faces of the β-sheet dimers form a hydrophobic core.
    • The diffusion coefficients of the oligomers of peptides 3j and 3k are about 0.80-0.85 times that of the tetramer of peptide 3a. The smaller diffusion coefficients of these peptides suggest that peptides 3j and 3k form higher oligomers, such as hexamers or octamers, rather than tetramers. ROESY experiments show that the oligomers of these peptides comprise edge-to-edge dimers. The higher oligomers may be thought of as small micelles in which the hydrophobic faces of the β-sheet dimers form a hydrophobic core.
  • 104
    • 34247878253 scopus 로고    scopus 로고
    • We have observed similar improvements in the folding of the 42-membered-ring macrocyclic peptides 2 upon placing Phe across from the aromatic ring of Hao. For details, see ref 18
    • We have observed similar improvements in the folding of the 42-membered-ring macrocyclic peptides 2 upon placing Phe across from the aromatic ring of Hao. For details, see ref 18.
  • 106
    • 34247873548 scopus 로고    scopus 로고
    • 2O solution of peptide 3m from 1.0 mM to 16.0 mM results in similar downfield shifting.
    • 2O solution of peptide 3m from 1.0 mM to 16.0 mM results in similar downfield shifting.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.