Simple Structural Requirements for Sequence-Selective Peptide Receptors? Tripeptide Binding by a Podand Ionophore

Journal of Organic Chemistry

Volumn 62, Issue 14, 1997, Pages 4785-4790

  Burger, Matthew T ^a   Still, W Clark ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001597672     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970256w     Document Type: Article

References (33)

1. Review: Still, W. C. Acc. Chem. Res. 1996, 29, 155 and references therein. See also: Albert, J. S.; Goodman, M. S.; Hamilton, A. D. J. Am. Chem. Soc. 1995, 117, 1143. Waymark, C. P.; Kilburn, J. D.; Gillies, I. Tetrahedron Lett. 1995, 17, 3051. Maletic, M.; Wennemers, H.; McDonald, D. Q.; Breslow, R.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1490. Cheng, Y.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1996, 118, 1813. Shao, Y.; Still, W. C. J. Org. Chem. 1996, 61, 6086.
2. Review: Still, W. C. Acc. Chem. Res. 1996, 29, 155 and references therein. See also: Albert, J. S.; Goodman, M. S.; Hamilton, A. D. J. Am. Chem. Soc. 1995, 117, 1143. Waymark, C. P.; Kilburn, J. D.; Gillies, I. Tetrahedron Lett. 1995, 17, 3051. Maletic, M.; Wennemers, H.; McDonald, D. Q.; Breslow, R.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1490. Cheng, Y.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1996, 118, 1813. Shao, Y.; Still, W. C. J. Org. Chem. 1996, 61, 6086.
3. Review: Still, W. C. Acc. Chem. Res. 1996, 29, 155 and references therein. See also: Albert, J. S.; Goodman, M. S.; Hamilton, A. D. J. Am. Chem. Soc. 1995, 117, 1143. Waymark, C. P.; Kilburn, J. D.; Gillies, I. Tetrahedron Lett. 1995, 17, 3051. Maletic, M.; Wennemers, H.; McDonald, D. Q.; Breslow, R.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1490. Cheng, Y.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1996, 118, 1813. Shao, Y.; Still, W. C. J. Org. Chem. 1996, 61, 6086.
4. Review: Still, W. C. Acc. Chem. Res. 1996, 29, 155 and references therein. See also: Albert, J. S.; Goodman, M. S.; Hamilton, A. D. J. Am. Chem. Soc. 1995, 117, 1143. Waymark, C. P.; Kilburn, J. D.; Gillies, I. Tetrahedron Lett. 1995, 17, 3051. Maletic, M.; Wennemers, H.; McDonald, D. Q.; Breslow, R.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1490. Cheng, Y.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1996, 118, 1813. Shao, Y.; Still, W. C. J. Org. Chem. 1996, 61, 6086.
5. Review: Still, W. C. Acc. Chem. Res. 1996, 29, 155 and references therein. See also: Albert, J. S.; Goodman, M. S.; Hamilton, A. D. J. Am. Chem. Soc. 1995, 117, 1143. Waymark, C. P.; Kilburn, J. D.; Gillies, I. Tetrahedron Lett. 1995, 17, 3051. Maletic, M.; Wennemers, H.; McDonald, D. Q.; Breslow, R.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1490. Cheng, Y.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1996, 118, 1813. Shao, Y.; Still, W. C. J. Org. Chem. 1996, 61, 6086.
6. Review: Still, W. C. Acc. Chem. Res. 1996, 29, 155 and references therein. See also: Albert, J. S.; Goodman, M. S.; Hamilton, A. D. J. Am. Chem. Soc. 1995, 117, 1143. Waymark, C. P.; Kilburn, J. D.; Gillies, I. Tetrahedron Lett. 1995, 17, 3051. Maletic, M.; Wennemers, H.; McDonald, D. Q.; Breslow, R.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1490. Cheng, Y.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1996, 118, 1813. Shao, Y.; Still, W. C. J. Org. Chem. 1996, 61, 6086.
7. LaBrenz, S. R.; Kelly, J. W. J. Am. Chem. Soc. 1995, 117, 3887. Gennari, C.; Nestler, H. P.; Salom, B.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1765. Lowik, D. W. P. M.; Mulders, S. J. E.; Cheng, Y.; Shao, Y.; Liskamp, R. M. J. Tetrahedron Lett. 1996, 34, 8253.
8. LaBrenz, S. R.; Kelly, J. W. J. Am. Chem. Soc. 1995, 117, 3887. Gennari, C.; Nestler, H. P.; Salom, B.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1765. Lowik, D. W. P. M.; Mulders, S. J. E.; Cheng, Y.; Shao, Y.; Liskamp, R. M. J. Tetrahedron Lett. 1996, 34, 8253.
9. LaBrenz, S. R.; Kelly, J. W. J. Am. Chem. Soc. 1995, 117, 3887. Gennari, C.; Nestler, H. P.; Salom, B.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1765. Lowik, D. W. P. M.; Mulders, S. J. E.; Cheng, Y.; Shao, Y.; Liskamp, R. M. J. Tetrahedron Lett. 1996, 34, 8253.
10. Yoon, S. S.; Still, W. C. Tetrahedron 1995, 57, 567.
11. (a) Wang, X.; Erickson, S. D.; Iimori, T.; Still, W. C. J. Am. Chem. Soc. 1992, 114, 4128.
12. (b) Armstrong, A.; Still, W. C. J. Org. Chem. 1992, 57, 4580.
13. (c) Burger, M. T.; Armstrong, A.; Guarnieri, F.; McDonald, D. Q.; Still, W. C. J. Am. Chem. Soc. 1994, 116, 3573.
14. (d) Li, G.; Still, W. C. J. Org. Chem. 1991, 56, 6964.
15. Jackson, D. Y. Synth. Commun. 1988, 18, 337.
16. Reetz, M. T.; Gansauer, A. Tetrahedron 1993, 49, 6025.
17. Burger, M. T.; Still, W. C. J. Org. Chem. 1996, 61, 775.
18. Danishefsky, S. J.; Pearson, W. H.; Harvey, D. F.; Maring, C. J.; Springer, J. P. J. Am. Chem. Soc. 1985, 107, 1256.
19. Danishefsky, S. J.; Kobayashi, S.; Kerwin, J. F. J. Org. Chem. 1982, 47, 1981.
20. Actually, 24 389 is the maximum possible number of tripeptides in our library. In fact, the actual number of peptides we make and screen may be less than this due to library defects and sampling statistics. Library Defects. While solid phase peptide synthesis chemistry is very good, it is not perfect and some sequences may be present in significantly lower yields than others or even absent. Sampling Statistics. In any finite, random sample of a library (e.g. those we screen), probability dictates that some sequences will be overrepresented and others will be underrepresented (and in the extreme may even be absent). Thus in the screening assays we use here, any presence of binding is a significant result but any particular absence of binding may not be. We minimize such problems by using multiple couplings to drive each peptide coupling step to completion (as indicated by a negative Kaiser test) and by screening samples of the library containing ≥3 times as many beads as sequences (3 times should include >95% of all sequences in the library according to Poisson statistics).
21. Ohlmeyer, M. J.; Swanson, R. J.; Dillard, L. W.; Reader, J. C.; Asouline, G.; Kobayahi, R.; Wigler, M.; Still, W. C. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 10922.
22. TentaGel S from Rapp Polymere. Bayer, E. Angew. Chem., Int. Ed. Engl. 1991, 30, 113.
23. AAn = Gly, n-Ala, L-Ala, D-Val, L-Val, n-Phe, L-Phe, n-Leu, L-Leu, D-Pro, L-Pro, D-Asp(O-tBu), L-Asp(O-tBu), D-Glu(O-tBu), L-Glu(O-tBu), D-Asn(N-Tr), L-Asn(N-Tr), D-Gln(N-Tr), L-Gln(N-Tr), D-His(N-Tr), L-His(N-Tr), D-Lys(N-Boc), L-Lys(N-Boc), D-Arg(N-Pmc), L-Arg(N-pmc), D-Ser(O-tBu), L-Ser(O-tBu), D-Thr(O-tBu), L-Thr(O-tBu).
24. It is possible that some of the acid-sensitive side chain-protecting groups were lost during the day-long assays in acidic (HOAc) chloroform. This may explain the minor selectivity trend for AA3 = Arg as it will be shown that the major selectivity with the deprotected library also involves AA3 = Arg. For Arg(N-Pmc) protection data, see: Ramage, R.; Green, J. Tetrahedron Lett. 1987, 28, 2287.
25. Chalmers, D. K.; Marshall, G. R. J. Am. Chem. Soc. 1995, 117, 5927 and references therein.
26. Wennemers, H.; Still, W. C. Tetrahedron Lett. 1994, 35, 6417.
27. For example: Liang, R.; Van, L.; Loebach, J.; Ge, M.; Uozumi, Y.; Sekanina, K.; Horan, N.; Gildersleeve, J.; Thompson, C.; Smith, A.; Biswas, K.; Still, W. C.; Kahne, D. Science 1996, 274, 1520.
28. In published work, solid phase peptide binding results with small molecule receptors were compared with binding experiments in free solution: Borchardt, A.; Still, W. C. J. Am. Chem. Soc. 1994, 116, 373. Borchardt, A.; Still, W. C. J. Am. Chem., Soc. 1994, 116, 7467. Carrasco, M. R.; Still, W. C. Chem. Biol. 1995, 2, 205. Maletic, M.; Wennemers, H.; McDonald, D. Q.; Breslow, R. C.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1490. In different systems, peptides on a solid phase binding to a small molecule receptor in solution were resynthesized and tested in solution for binding the receptor on a solid phase: Gasparrini, F.; Misiti, D.; Villani, C.; Borchardt, A.; Burger, M. T.; Still, W. C. J. Org. Chem. 1995, 60, 4314. Chen, C.-T.; Wagner, H.; Still, W. C. Science 1997, submitted.
29. In published work, solid phase peptide binding results with small molecule receptors were compared with binding experiments in free solution: Borchardt, A.; Still, W. C. J. Am. Chem. Soc. 1994, 116, 373. Borchardt, A.; Still, W. C. J. Am. Chem., Soc. 1994, 116, 7467. Carrasco, M. R.; Still, W. C. Chem. Biol. 1995, 2, 205. Maletic, M.; Wennemers, H.; McDonald, D. Q.; Breslow, R. C.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1490. In different systems, peptides on a solid phase binding to a small molecule receptor in solution were resynthesized and tested in solution for binding the receptor on a solid phase: Gasparrini, F.; Misiti, D.; Villani, C.; Borchardt, A.; Burger, M. T.; Still, W. C. J. Org. Chem. 1995, 60, 4314. Chen, C.-T.; Wagner, H.; Still, W. C. Science 1997, submitted.
30. In published work, solid phase peptide binding results with small molecule receptors were compared with binding experiments in free solution: Borchardt, A.; Still, W. C. J. Am. Chem. Soc. 1994, 116, 373. Borchardt, A.; Still, W. C. J. Am. Chem., Soc. 1994, 116, 7467. Carrasco, M. R.; Still, W. C. Chem. Biol. 1995, 2, 205. Maletic, M.; Wennemers, H.; McDonald, D. Q.; Breslow, R. C.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1490. In different systems, peptides on a solid phase binding to a small molecule receptor in solution were resynthesized and tested in solution for binding the receptor on a solid phase: Gasparrini, F.; Misiti, D.; Villani, C.; Borchardt, A.; Burger, M. T.; Still, W. C. J. Org. Chem. 1995, 60, 4314. Chen, C.-T.; Wagner, H.; Still, W. C. Science 1997, submitted.
31. In published work, solid phase peptide binding results with small molecule receptors were compared with binding experiments in free solution: Borchardt, A.; Still, W. C. J. Am. Chem. Soc. 1994, 116, 373. Borchardt, A.; Still, W. C. J. Am. Chem., Soc. 1994, 116, 7467. Carrasco, M. R.; Still, W. C. Chem. Biol. 1995, 2, 205. Maletic, M.; Wennemers, H.; McDonald, D. Q.; Breslow, R. C.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1490. In different systems, peptides on a solid phase binding to a small molecule receptor in solution were resynthesized and tested in solution for binding the receptor on a solid phase: Gasparrini, F.; Misiti, D.; Villani, C.; Borchardt, A.; Burger, M. T.; Still, W. C. J. Org. Chem. 1995, 60, 4314. Chen, C.-T.; Wagner, H.; Still, W. C. Science 1997, submitted.
32. In published work, solid phase peptide binding results with small molecule receptors were compared with binding experiments in free solution: Borchardt, A.; Still, W. C. J. Am. Chem. Soc. 1994, 116, 373. Borchardt, A.; Still, W. C. J. Am. Chem., Soc. 1994, 116, 7467. Carrasco, M. R.; Still, W. C. Chem. Biol. 1995, 2, 205. Maletic, M.; Wennemers, H.; McDonald, D. Q.; Breslow, R. C.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1490. In different systems, peptides on a solid phase binding to a small molecule receptor in solution were resynthesized and tested in solution for binding the receptor on a solid phase: Gasparrini, F.; Misiti, D.; Villani, C.; Borchardt, A.; Burger, M. T.; Still, W. C. J. Org. Chem. 1995, 60, 4314. Chen, C.-T.; Wagner, H.; Still, W. C. Science 1997, submitted.
33. In published work, solid phase peptide binding results with small molecule receptors were compared with binding experiments in free solution: Borchardt, A.; Still, W. C. J. Am. Chem. Soc. 1994, 116, 373. Borchardt, A.; Still, W. C. J. Am. Chem., Soc. 1994, 116, 7467. Carrasco, M. R.; Still, W. C. Chem. Biol. 1995, 2, 205. Maletic, M.; Wennemers, H.; McDonald, D. Q.; Breslow, R. C.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1490. In different systems, peptides on a solid phase binding to a small molecule receptor in solution were resynthesized and tested in solution for binding the receptor on a solid phase: Gasparrini, F.; Misiti, D.; Villani, C.; Borchardt, A.; Burger, M. T.; Still, W. C. J. Org. Chem. 1995, 60, 4314. Chen, C.-T.; Wagner, H.; Still, W. C. Science 1997, submitted.