Chemical Evolution: A Model System That Selects and Amplifies a Receptor for the Tripeptide (D)Pro(L)Val(D)Val

Journal of Organic Chemistry

Volumn 63, Issue 4, 1998, Pages 904-905

  Hioki, Hideaki ^a   Clark Still, W ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542548456     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971782q     Document Type: Article

References (22)

1. Review: Szostak, J. W. Acc. Chem. Res. 1996, 29, 103.
2. For progress in molecular amplification by replication, see: Orgel, L. E. Acc. Chem. Res. 1995, 28, 109. Wintner, E. A.; Conn, M. M.; Rebek, J. Acc. Chem. Res. 1994, 27, 198.
3. For progress in molecular amplification by replication, see: Orgel, L. E. Acc. Chem. Res. 1995, 28, 109. Wintner, E. A.; Conn, M. M.; Rebek, J. Acc. Chem. Res. 1994, 27, 198.
4. The approach has precedents in classical synthetic organic chemistry. For example, in his total synthesis of steroids, Woodward was able to set up an equilibrium between the cis and trans Diels-Alder adducts of 1,3-butadiene and 2-methoxy-5-methyl-p-quinone and drive that equilibrium to the less stable trans adduct in 90% yield by crystallization. Woodward, R. B.; Sondheimer, F.; Taub, D.; Heusler, K.; McLamore, W. M. J. Am. Chem. Soc. 1952, 74, 4223.
5. (a) Still, W. C., Hauck, P.; Kempf, D. Tetrahedron Lett. 1987, 28, 2817.
6. (b) Goodwin, J. T.; Lynn, D. G. J. Am. Chem. Soc. 1992, 114, 9197.
7. Kramer, R.; Lehn, J.-M.; Marquis-Rigault, A. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 5394.
8. Eliseev, A. V.; Nelen, M. I. J. Am. Chem. Soc. 1997, 119, 1147.
9. (e) Huc, I.; Lehn, J.-M. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 2106.
10. (f) Swann, P. G.; Casanova, R. A.; Desai, A.; Frauenhoff, M. M.; Urbancic, M.; Slomczynska, U.; Hopfinger, A. J.; Le Breton, G. C.; Venton, D. L. Biopolym. 1996, 40, 617.
11. Review of sequence-selective peptide-binding host molecules: Still, W. C. Acc. Chem. Res. 1996, 29, 155.
12. (a) Wennemers, H.; Yoon, S. S.; Still, W. C. J. Org. Chem. 1995, 60, 1108.
13. (b) Shao, Y.; Still, W. C. J. Org. Chem. 1996, 61, 6086.
14. Pan, Z.; Still, W. C. Tetrahedron Lett. 1996, 37, 8699.
15. Iorio, E. J.; Still, W. C. Bioorg. Med. Chem. Lett. 1996, 2673.
16. (e) Torniero, M.; Still, W. C. Tetrahedron 1997, 53, 8739.
17. 3) members having the structure Ac-AA1-AA2-AA3-polystyrene where AAn = Gly, (D and L) Ala, Ser, Val, Pro, Asn, Gln, Lys. See ref 5 for details.
18. Similar equilibrium constants were obtained with control equilibrations in the presence of acetylated aminomethylpolystyrene (same quantity of resin used in the equilibrations in the presence of Ac(D)Pro(L)Val(D)ValPS).
19. 3, though we can detect weak binding at 10-fold higher concentrations.
20. Konishi, H.; Nakamura, T.; Ohata, K.; Kobayashi, K.; Morikawa, O. Tetrahedron Lett. 1996, 37, 7383; Rowan, S. J.; Hamilton, D. G.; Brady, P. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1997, 119, 2578. Rowan, S. J.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1997, 1407.
21. Konishi, H.; Nakamura, T.; Ohata, K.; Kobayashi, K.; Morikawa, O. Tetrahedron Lett. 1996, 37, 7383; Rowan, S. J.; Hamilton, D. G.; Brady, P. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1997, 119, 2578. Rowan, S. J.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1997, 1407.
22. Konishi, H.; Nakamura, T.; Ohata, K.; Kobayashi, K.; Morikawa, O. Tetrahedron Lett. 1996, 37, 7383; Rowan, S. J.; Hamilton, D. G.; Brady, P. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1997, 119, 2578. Rowan, S. J.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1997, 1407.