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Volumn 47, Issue 32, 2006, Pages 5801-5805

Synthesis and evaluation of α-helix mimetics based on a trans-fused polycyclic ether: sequence-selective binding to aspartate pairs in α-helical peptides

Author keywords

Helix mimetic; Molecular recognition; Polycyclic ether; Scaffold

Indexed keywords

ASPARTIC ACID; ETHER DERIVATIVE; GUANIDINE; HYDROXYL GROUP; PEPTIDE; POLYCYCLIC ETHER; RECEPTOR; UNCLASSIFIED DRUG;

EID: 33745737798     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.05.170     Document Type: Article
Times cited : (28)

References (46)
  • 9
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    • Selected examples for nonpeptide based α-helix mimetics, see:
    • Selected examples for nonpeptide based α-helix mimetics, see:. Albert J.S., Peczuh M.W., and Hamilton A.D. Bioorg. Med. Chem. 5 (1997) 1455
    • (1997) Bioorg. Med. Chem. , vol.5 , pp. 1455
    • Albert, J.S.1    Peczuh, M.W.2    Hamilton, A.D.3
  • 15
    • 22844434675 scopus 로고    scopus 로고
    • Murata et al. recently reported the interaction of the ladder-shaped polycyclic ether with the α-helix that induces dissociation of glycopholin oligomers, see:
    • Murata et al. recently reported the interaction of the ladder-shaped polycyclic ether with the α-helix that induces dissociation of glycopholin oligomers, see:. Mori M., Oishi T., Matsuoka S., Ujihara S., Matsumori N., Murata M., Satake M., Oshima Y., Matsusita N., Aimoto S. Bioorg. Med. Chem. 13 (2005) 5099
    • (2005) Bioorg. Med. Chem. , vol.13 , pp. 5099
    • Mori, M.1    Oishi, T.2    Matsuoka, S.3    Ujihara, S.4    Matsumori, N.5    Murata, M.6    Satake, M.7    Oshima, Y.8    Matsusita, N.9    Aimoto, S.10
  • 16
    • 11144320327 scopus 로고    scopus 로고
    • For recent reviews and accounts, see:
    • For recent reviews and accounts, see:. Fujiwara K., and Murai A. Bull. Chem. Soc. Jpn. 77 (2004) 2129
    • (2004) Bull. Chem. Soc. Jpn. , vol.77 , pp. 2129
    • Fujiwara, K.1    Murai, A.2
  • 25
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    • and references cited therein
    • Schug K.A., and Lindner W. Chem. Rev. 105 (2005) 67 and references cited therein
    • (2005) Chem. Rev. , vol.105 , pp. 67
    • Schug, K.A.1    Lindner, W.2
  • 35
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    • note
    • 2 were unsuccessful.
  • 36
    • 33745762897 scopus 로고    scopus 로고
    • note
    • The stereochemistries of 19 and 20 were unambiguously determined by NMR analysis after acetylation. The coupling constants between H9 and H10 for the triacetate of 19 and the diacetate of 20 were J = 6.0 and 9.0 Hz, respectively. A plausible explanation for the stereochemical outcome at C9 is as follows.{A figure is presented}
  • 37
    • 33745747657 scopus 로고    scopus 로고
    • note
    • The stereochemistry of 18 was unambiguously determined by NOE experiments.{A figure is presented}
  • 38
    • 33745760687 scopus 로고    scopus 로고
    • note
    • 13a.
  • 39
    • 33745742988 scopus 로고    scopus 로고
    • note
    • Reduction of the corresponding acetate in place of benzoate 15 resulted in the formation of the desired tetracyclic ether in a lower yield (36%). This suggests that the electron-withdrawing nature of the benzoate group plays an important role in this conversion.
  • 41
    • 33745742390 scopus 로고    scopus 로고
    • note
    • The peptide concentration was determined by the BCA (bicinchoninic acid) protein assay (Pierce) using BSA (bovine serum albumin) as a standard.
  • 42
    • 33745744918 scopus 로고    scopus 로고
    • note
    • 24 The percentages of helicity of the peptides were determined as i + 3 (63%), i + 4 (56%), i + 5 (71%), and i + 11 (64%) by monitoring the ellipticity at 222 nm using the average of 120 points collected over 60 s.
  • 44
    • 33745746158 scopus 로고    scopus 로고
    • note
    • To ensure that the mode of binding was 1:1, a Job CD titration was conducted with peptide i + 4 and receptor 2 in 10% water/methanol at 25 °C. Maximum signal change was observed when the molar composition of i + 4 and 2 were equivalent, indicative of the 1:1 complex formation.{A figure is presented}


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.