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Volumn 4, Issue 11, 2003, Pages 1232-1238

Peptide Binding by One-Armed Receptors in Water: Screening of a Combinatorial Library for the Binding of Val-Val-lle-Ala

Author keywords

Combinatorial chemistry; Guanidinium cations; Molecular recognition; Peptides; Receptors

Indexed keywords

PEPTIDE DERIVATIVE; PEPTIDE LIBRARY; RECOMBINANT RECEPTOR; UNCLASSIFIED DRUG; VALYLVALYLISOLEUCYLALANINE;

EID: 0344012530     PISSN: 14394227     EISSN: None     Source Type: Journal    
DOI: 10.1002/cbic.200300613     Document Type: Article
Times cited : (51)

References (51)
  • 1
    • 0034228707 scopus 로고    scopus 로고
    • For review articles on artificial peptide receptors see: a) M. W. Peczuh, A. D. Hamilton, Chem. Rev. 2000, 100, 2479-2494;
    • (2000) Chem. Rev. , vol.100 , pp. 2479-2494
    • Peczuh, M.W.1    Hamilton, A.D.2
  • 3
    • 0011920689 scopus 로고
    • c) H. J. Schneider, Angew. Chem. 1993, 105, 890-892; Angew. Chem. Int. Ed. Engl. 1993, 32, 848-850;
    • (1993) Angew. Chem. , vol.105 , pp. 890-892
    • Schneider, H.J.1
  • 4
    • 33748812439 scopus 로고
    • c) H. J. Schneider, Angew. Chem. 1993, 105, 890-892; Angew. Chem. Int. Ed. Engl. 1993, 32, 848-850;
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 848-850
  • 16
    • 0032978519 scopus 로고    scopus 로고
    • The importance of the interplay between hydrophobic interactions and H-bonds ("hydrophobic cluster formation") has been demonstrated, for example, by Kelly in his work on β-sheet nucleators: a) P. Chitnumsub, W. R. Fiori, H. A. Lashuel, H. Diaz, J. W. Kelly, Bioorg. Med. Chem. 1999, 7, 39-59;
    • (1999) Bioorg. Med. Chem. , vol.7 , pp. 39-59
    • Chitnumsub, P.1    Fiori, W.R.2    Lashuel, H.A.3    Diaz, H.4    Kelly, J.W.5
  • 22
    • 0029896354 scopus 로고    scopus 로고
    • d) B. A. Yankner, Neuron 1996, 16, 921-932.
    • (1996) Neuron , vol.16 , pp. 921-932
    • Yankner, B.A.1
  • 24
    • 0000485604 scopus 로고    scopus 로고
    • a) J. J. Lavigne, E. V. Anslyn, Angew. Chem. 2001, 113, 3212-3225; Angew. Chem. Int. Ed. 2001, 40, 3118-3130;
    • (2001) Angew. Chem. , vol.113 , pp. 3212-3225
    • Lavigne, J.J.1    Anslyn, E.V.2
  • 25
    • 0035801512 scopus 로고    scopus 로고
    • a) J. J. Lavigne, E. V. Anslyn, Angew. Chem. 2001, 113, 3212-3225; Angew. Chem. Int. Ed. 2001, 40, 3118-3130;
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 3118-3130
  • 34
    • 0001770672 scopus 로고    scopus 로고
    • Artificial Anion Hosts: Concepts for Structure and Guest Binding
    • F. P. Schmidtchen, (Eds.: A. Bianchi, K. Bowman-James, E. García-España), Wiley-VCH, Weinheim
    • c) "Artificial Anion Hosts: Concepts for Structure and Guest Binding" F. P. Schmidtchen in Supramolecular Chemistry of Anions (Eds.: A. Bianchi, K. Bowman-James, E. García-España), Wiley-VCH, Weinheim, 1997, pp. 79-146;
    • (1997) Supramolecular Chemistry of Anions , pp. 79-146
  • 35
    • 0000571928 scopus 로고    scopus 로고
    • Structural and Topological Aspects of Anion Coordination
    • J. L. Atwood, J. W. Steed, (Eds.: A. Bianchi, K. Bowman-James, E. García-España), Wiley-VCH: New York
    • d) "Structural and Topological Aspects of Anion Coordination" J. L. Atwood, J. W. Steed in Supramolecular Chemistry of Anions (Eds.: A. Bianchi, K. Bowman-James, E. García-España), Wiley-VCH: New York, 1997, pp. 147-216.
    • (1997) Supramolecular Chemistry of Anions , pp. 147-216
  • 36
    • 0042508739 scopus 로고    scopus 로고
    • We were recently able to show that one-armed cationic receptors of this general type attached to a solid support are capable of binding an anionic tetrapeptide, at least in organic solvents (DMSO, methanol): C. Schmuck, M. Heil, Org. Biomol. Chem. 2003, 1, 633-636.
    • (2003) Org. Biomol. Chem. , vol.1 , pp. 633-636
    • Schmuck, C.1    Heil, M.2
  • 39
    • 85007630016 scopus 로고    scopus 로고
    • note
    • The successful synthesis of the receptors on the solid support was monitored for selected examples by solid-state MAS-NMR and ESI-MS experiments and their respective cleavage from the solid support and subsequent isolation; see also Experimental Section.
  • 44
    • 85007650545 scopus 로고    scopus 로고
    • note
    • ass for each receptor was calculated.
  • 47
    • 85007639431 scopus 로고    scopus 로고
    • note
    • For a typical UV titration, aliquots of the substrate 10 (0.58 mM) were added to a solution of the receptor (0.0546 mM) in bis-tris buffer (0.78 mM, pH 6.1). The UV spectra were recorded after each addition. Analysis of the data was performed with the Specfit/32 software program from Spectrum Software Associates.
  • 48
    • 85007639296 scopus 로고    scopus 로고
    • note
    • -1), did not give any reasonable data. The binding constant was too low to be measured accurately in free solution by UV titration, which is again in good agreement with the rather poor binding affinity of this specific receptor observed in the on-bead assay.
  • 51
    • 85007654065 scopus 로고    scopus 로고
    • note
    • Because of the limited solubilities both of the free peptide and of the receptors at concentrations > 10mM in aqueous solvents, the NMR studies had to be performed in DMSO. Although the relative importance of H-bonds/ ion-pairing versus hydrophobic interactions should be shifted towards the hydrophobic interactions in water, the observation of the H-bonded pattern required for a β sheet in DMSO is also a necessary prerequisite for its occurrence in water.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.