Simple synthetic receptors that bind peptides in water

Tetrahedron

Volumn 53, Issue 26, 1997, Pages 8739-8750

  Torneiro, Mercedes ^a   Still, W Clark ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SYNTHETIC PEPTIDE;

ARTICLE; BINDING AFFINITY; HYDROPHILICITY; MOLECULAR DYNAMICS; PARTICLE SIZE; PEPTIDE ANALYSIS; PRIORITY JOURNAL; PROTEIN SYNTHESIS; RECEPTOR BINDING;

EID: 0030854052     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)90388-4     Document Type: Article

References (26)

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2. Review: Still, W.C. Accnts. Chem. Res. 1996, 29, 155. See also: Maletic, M.; Wennemers, H.; McDonald, D.Q.; Breslow, R.; Still, W.C. Angew. Chem. Intl. Ed. Engl. 1996, 35, 1490.
3. a) Wennemers, H.; Yoon, S.S.; Still, W.C. J. Org. Chem. 1995, 60, 1108;
4. b) Shao, Y.; Still, W.C. J. Org. Chem. 1996, 61, 6086;
5. c) Iorio, E.J.; Still, W.C. Bioorg. Med. Chem. Lett. 1996, 6, 2673;
6. d) Pan, Z.; Still, W.C. Tetrahedron Lett. 1996, 37, 8699.
7. a) Boyce, R.; Li, G.; Nestler, H.P.; Suenega, T.; Still, W.C. J. Am. Chem. Soc. 1994, 116, 7955;
8. b) LaBrenz, S.R.; Kelly, J.W. J. Am. Chem. Soc. 1995, 117, 1655;
9. c) Gennari, C.; Nestler, H.P.; Salom, B.; Still, W.C. Angew. Chem. Intl. Ed. Engl. 1995, 34, 1765;
10. d) Burger, M.T.; Still, W.C. J. Org. Chem. 1995, 60, 7382;
11. e) Goodman, M.S.; Jubian, V.; Linton, B.; Hamilton, A.D. J. Am. Chem. Soc. 1995, 117, 1160;
12. f) Cheng, Y.; Suenaga, T.; Still, W.C. J. Am. Chem. Soc. 1996, 118, 1813;
13. g) Bonnat, M.; Bradley, M.; Kilburn, J.D. Tetrahedron Lett. 1996, 37, 5409.
14. E.g. Zimmerman, S.C. Top. Curr. Chem. 1993, 165, 71; Jeong, K.-S.; Muehldorf, A.V.; Rebek, J. J. Am. Chem. Soc. 1990, 112, 6144; Jacobsen, E.N.; Zhang, W.; Muci, A.R.; Ecker, J.R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063; ref 6.
15. E.g. Zimmerman, S.C. Top. Curr. Chem. 1993, 165, 71; Jeong, K.-S.; Muehldorf, A.V.; Rebek, J. J. Am. Chem. Soc. 1990, 112, 6144; Jacobsen, E.N.; Zhang, W.; Muci, A.R.; Ecker, J.R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063; ref 6.
16. E.g. Zimmerman, S.C. Top. Curr. Chem. 1993, 165, 71; Jeong, K.-S.; Muehldorf, A.V.; Rebek, J. J. Am. Chem. Soc. 1990, 112, 6144; Jacobsen, E.N.; Zhang, W.; Muci, A.R.; Ecker, J.R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063; ref 6.
17. Torneiro, M.; Still, W.C. J. Am. Chem. Soc. 1995, 117, 5887.
18. Sharpless, K.B.; Amberg, W.; Bennani, Y.L.; Crispino, G.A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Murikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.L. J. Org. Chem. 1992, 57, 2768.
19. Yoon, S.S.; Still, W.C. Tetrahedron 1995, 51, 567.
20. Wennemers, H.; Still, W.C. Tetrahedron Lett. 1994, 35, 6413.
21. TentaGel S from Rapp Polymere. Bayer, E. Angew. Chem. Intl. Ed. Engl. 1991, 30, 113.
22. Ohlmeyer, M.H.J.; Swanson, R.N.; Dillard, L.W.; Reader, J.C.; Asouline, G.; Kobayashi, R.; Wigler, M.; Still, W.C. Proc. Natl. Acad. Sci. USA 1993, 90, 10922.
23. The polystyrene-bound tripeptide library used to screen 1 in chloroform did not contain Leu but did contain the related hydrophobic amino acid Val.
24. For the other example, see references 5 and 7.
25. Gassman, P.G.; Bonser, S.M.; Mlinaric-Majerski, K. J. Am. Chem. Soc. 1989, 11, 2652.
26. Yoon, S.S.; Still, W.C. J. Am. Chem. Soc. 1993, 115, 823.