Synthesis of calix[4]arene library substituted with peptides at the upper rim

Tetrahedron Letters

Volumn 45, Issue 3, 2004, Pages 561-564

  Hioki, Hideaki ^a   Ohnishi, Yumiko ^a   Kubo, Miwa ^a   Nashimoto, Emi ^a   Kinoshita, Yukinori ^a   Samejima, Miho ^a   Kodama, Mitsuaki ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

Binding assay; Calixarenes; Chemosensors; Combinatorial library

Indexed keywords

CALIXARENE; FLUORESCENT DYE; OLIGOPEPTIDE; PENTAPEPTIDE; PEPTIDE LIBRARY; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

AMINO TERMINAL SEQUENCE; ARTICLE; BINDING ASSAY; BINDING SITE; CHEMOSENSITIVITY; PROTEIN BINDING; PROTEIN CONFORMATION; PROTEIN TARGETING; PROTON NUCLEAR MAGNETIC RESONANCE; SCREENING; SYNTHESIS;

ARENE;

EID: 0346993610     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.215     Document Type: Article

References (19)

1. For selected books on calixarene chemistry, see: Gutsche C.D. Calixarenes Revisited. Stoddart F.J. Monographs in Supramolecular Chemistry. Vol. 6:1998;The Royal Society of Chemistry, Cambridge, Mandolini L., Ungaro R. Calixarenes in Action. 2000;Imperial College Press, London.
2. For selected books on calixarene chemistry, see: Gutsche C.D. Calixarenes Revisited. Stoddart F.J. Monographs in Supramolecular Chemistry. Vol. 6:1998;The Royal Society of Chemistry, Cambridge, Mandolini L., Ungaro R. Calixarenes in Action. 2000;Imperial College Press, London.
3. Hioki H., Kubo M., Yoshida H., Bando M., Ohnishi Y., Kodama M. Tetrahedron Lett. 43:2002;7949-7952.
4. For recent review for receptor libraries, see: Peczuh M.W., Hamilton A.D. Chem. Rev. 100:2000;2479-2494 Lavigne J.J., Anslyn E.V. Angew. Chem., Int. Ed. 40:2001;3118-3130.
5. For recent review for receptor libraries, see: Peczuh M.W., Hamilton A.D. Chem. Rev. 100:2000;2479-2494 Lavigne J.J., Anslyn E.V. Angew. Chem., Int. Ed. 40:2001;3118-3130.
6. For a recent review on calixarene-based chemosensors, see: Diamond D., Nolan K. Anal. Chem. 73:2001;22A-29A.
7. Hioki H., Yamada T., Fujioka C., Kodama M. Tetrahedron Lett. 40:1999;6821-6825.
8. A solid supported calix[4]arene substituted by trialanine on the upper rim was reported, see: Shuker S.B., Esterbrook J., Gonzalez J. Synlett. 23:2001;210-213.
9. As protein receptors, calix[4]arenes modified at the upper rim by cyclic peptide were reported, see: Blaskovich M.A., Lin Q., Delarue F.L., Sun J., Park H.S., Coppola D., Hamilton A.D., Sebti S.M. Nature Biotechnol. 18:2000;1065-1070. and references cited therein.
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11. Gutsche C.D., Stoddart F.J. Calixarenes, Monographs in Supramolecular Chemistry. Vol. 1:1989;The Royal Society of Chemistry, Cambridge.
12. Hioki H., Nakaoka R., Maruyama A., Kodama M. J. Chem. Soc., Perkin. Trans. 1. 2001;3265-3268.
13. 2 (v/v) at room temperature for 1 h.
14. 2 (v/v) in the presence of PhSH (30 equiv) at room temperature for 1 h.
15. Analyte 7b possesses a palmitoyl group at the N-terminal (R) instead of the dye moiety in 7a . The N-terminal was changed from the dye to the palmitoyl group because the fluorescence emission of 8 overlapped with the absorption of 7a.
16. -3. The result indicates that the emission at 470 nm was assigned to an intramolecular excimer.
17. 17.
18. Jin T., Ichikawa K., Koyama T. J. Chem. Soc., Chem. Commun. 1992;499-501.
19. Connors K.A. Binding Constants. 1987;Wiley-Interscience. p 141.