Tweezers with different bite: Increasing the affinity of synthetic receptors by varying the hinge part

Angewandte Chemie - International Edition

Volumn 37, Issue 13-14, 1998, Pages 1846-1850

  Löwik, Dennis W P M ^a   Weingarten, W David ^b   Broekema, Matthias ^a   Brouwer, Arwin J ^a   Still, W Clark ^b   Liskamp, Rob M J ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

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

Author keywords

Combinatorial chemistry; Peptides; Peptidomimetics; Receptors; Sulfonamides

Indexed keywords

EID: 0039302822     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980803)37:13/14<1846::AID-ANIE1846>3.0.CO;2-E     Document Type: Article

References (24)

1. S. C. Zimmerman, W. Wu, Z. Zeng, J. Am. Chem. Soc. 1991, 113, 196-201; R. Boyce, G. Li, H. P. Nestler, T. Suenaga, W. C. Still, ibid. 1994, 116, 7955-7956; S. R. Labrenz, J. W. Kelly, ibid. 1995, 117, 1655-1656; Y. Cheng, T. Suenaga, W. C. Still, ibid. 1996, 118, 1813-1814; H. Wennemers, S. S. Yoon, W. C. Still, J. Org. Chem. 1995, 60, 1108-1109; C. Gennari, H. P. Nestler, B. Salom, W. C. Still, Angew. Chem. 1995, 107, 1894-1896; Angew. Chem. Int. Ed. Engl. 1995, 34, 1765-1768.
2. S. C. Zimmerman, W. Wu, Z. Zeng, J. Am. Chem. Soc. 1991, 113, 196-201; R. Boyce, G. Li, H. P. Nestler, T. Suenaga, W. C. Still, ibid. 1994, 116, 7955-7956; S. R. Labrenz, J. W. Kelly, ibid. 1995, 117, 1655-1656; Y. Cheng, T. Suenaga, W. C. Still, ibid. 1996, 118, 1813-1814; H. Wennemers, S. S. Yoon, W. C. Still, J. Org. Chem. 1995, 60, 1108-1109; C. Gennari, H. P. Nestler, B. Salom, W. C. Still, Angew. Chem. 1995, 107, 1894-1896; Angew. Chem. Int. Ed. Engl. 1995, 34, 1765-1768.
3. S. C. Zimmerman, W. Wu, Z. Zeng, J. Am. Chem. Soc. 1991, 113, 196-201; R. Boyce, G. Li, H. P. Nestler, T. Suenaga, W. C. Still, ibid. 1994, 116, 7955-7956; S. R. Labrenz, J. W. Kelly, ibid. 1995, 117, 1655-1656; Y. Cheng, T. Suenaga, W. C. Still, ibid. 1996, 118, 1813-1814; H. Wennemers, S. S. Yoon, W. C. Still, J. Org. Chem. 1995, 60, 1108-1109; C. Gennari, H. P. Nestler, B. Salom, W. C. Still, Angew. Chem. 1995, 107, 1894-1896; Angew. Chem. Int. Ed. Engl. 1995, 34, 1765-1768.
4. S. C. Zimmerman, W. Wu, Z. Zeng, J. Am. Chem. Soc. 1991, 113, 196-201; R. Boyce, G. Li, H. P. Nestler, T. Suenaga, W. C. Still, ibid. 1994, 116, 7955-7956; S. R. Labrenz, J. W. Kelly, ibid. 1995, 117, 1655-1656; Y. Cheng, T. Suenaga, W. C. Still, ibid. 1996, 118, 1813-1814; H. Wennemers, S. S. Yoon, W. C. Still, J. Org. Chem. 1995, 60, 1108-1109; C. Gennari, H. P. Nestler, B. Salom, W. C. Still, Angew. Chem. 1995, 107, 1894-1896; Angew. Chem. Int. Ed. Engl. 1995, 34, 1765-1768.
5. S. C. Zimmerman, W. Wu, Z. Zeng, J. Am. Chem. Soc. 1991, 113, 196-201; R. Boyce, G. Li, H. P. Nestler, T. Suenaga, W. C. Still, ibid. 1994, 116, 7955-7956; S. R. Labrenz, J. W. Kelly, ibid. 1995, 117, 1655-1656; Y. Cheng, T. Suenaga, W. C. Still, ibid. 1996, 118, 1813-1814; H. Wennemers, S. S. Yoon, W. C. Still, J. Org. Chem. 1995, 60, 1108-1109; C. Gennari, H. P. Nestler, B. Salom, W. C. Still, Angew. Chem. 1995, 107, 1894-1896; Angew. Chem. Int. Ed. Engl. 1995, 34, 1765-1768.
6. S. C. Zimmerman, W. Wu, Z. Zeng, J. Am. Chem. Soc. 1991, 113, 196-201; R. Boyce, G. Li, H. P. Nestler, T. Suenaga, W. C. Still, ibid. 1994, 116, 7955-7956; S. R. Labrenz, J. W. Kelly, ibid. 1995, 117, 1655-1656; Y. Cheng, T. Suenaga, W. C. Still, ibid. 1996, 118, 1813-1814; H. Wennemers, S. S. Yoon, W. C. Still, J. Org. Chem. 1995, 60, 1108-1109; C. Gennari, H. P. Nestler, B. Salom, W. C. Still, Angew. Chem. 1995, 107, 1894-1896; Angew. Chem. Int. Ed. Engl. 1995, 34, 1765-1768.
7. S. C. Zimmerman, W. Wu, Z. Zeng, J. Am. Chem. Soc. 1991, 113, 196-201; R. Boyce, G. Li, H. P. Nestler, T. Suenaga, W. C. Still, ibid. 1994, 116, 7955-7956; S. R. Labrenz, J. W. Kelly, ibid. 1995, 117, 1655-1656; Y. Cheng, T. Suenaga, W. C. Still, ibid. 1996, 118, 1813-1814; H. Wennemers, S. S. Yoon, W. C. Still, J. Org. Chem. 1995, 60, 1108-1109; C. Gennari, H. P. Nestler, B. Salom, W. C. Still, Angew. Chem. 1995, 107, 1894-1896; Angew. Chem. Int. Ed. Engl. 1995, 34, 1765-1768.
8. D. W. P. M. Löwik, S. J. E. Mulders, Y. Cheng, Y. Shao, R. M. J. Liskamp, Tetrahedron Lett. 1996, 37, 8253-8256.
9. K. Kurz, M. G. Göbel, Helv. Chim. Acta 1996, 79, 1967-1979.
10. D. B. A. de Bont, G. H. Dijkstra, J. A. J. den Hartog, R. M. J. Liskamp, Bioorg. Med. Chem. Lett. 1996, 6, 3035-3040.
11. This hinge was successfully applied in the synthetic receptors of Still et al. see for example a) S. S. Yoon, W. C. Still, Tetrahedron 1995, 51, 567-578; b) Y. Shao, W. C. Still, J. Org. Chem. 1996, 62, 6086-6087; c) Z. Pan, W. C Still, Tetrahedron Lett. 1996, 37, 8699-8702; d) M. Torneiro, W. C. Still Tetrahedron 1997, 53, 8739-8750.
12. This hinge was successfully applied in the synthetic receptors of Still et al. see for example a) S. S. Yoon, W. C. Still, Tetrahedron 1995, 51, 567-578; b) Y. Shao, W. C. Still, J. Org. Chem. 1996, 62, 6086-6087; c) Z. Pan, W. C Still, Tetrahedron Lett. 1996, 37, 8699-8702; d) M. Torneiro, W. C. Still Tetrahedron 1997, 53, 8739-8750.
13. This hinge was successfully applied in the synthetic receptors of Still et al. see for example a) S. S. Yoon, W. C. Still, Tetrahedron 1995, 51, 567-578; b) Y. Shao, W. C. Still, J. Org. Chem. 1996, 62, 6086-6087; c) Z. Pan, W. C Still, Tetrahedron Lett. 1996, 37, 8699-8702; d) M. Torneiro, W. C. Still Tetrahedron 1997, 53, 8739-8750.
14. This hinge was successfully applied in the synthetic receptors of Still et al. see for example a) S. S. Yoon, W. C. Still, Tetrahedron 1995, 51, 567-578; b) Y. Shao, W. C. Still, J. Org. Chem. 1996, 62, 6086-6087; c) Z. Pan, W. C Still, Tetrahedron Lett. 1996, 37, 8699-8702; d) M. Torneiro, W. C. Still Tetrahedron 1997, 53, 8739-8750.
15. U. Nagel, E. Kinzel, J. Andrade, G. Prescher, Chem. Ber. 1986, 119, 3326-3343.
16. J. Skarzewski, A. Gupta, Tetrahedron Assym. 1997, 8, 1861-1867.
17. See reference [5a].
18. R. J. Pieters, I. Huc, J. Rebek, Jr., Chem. Eur. J. 1995, 1, 183-192.
19. F. Diederich, D. R. Carnanague, Helv. Chim. Acta 1994, 77, 800-818.
20. It was difficult to functionalize the hindered secondary hydroxy function in the diazabicyclononane part of the ligands with a suitable anchor molecule to which the dye had to be attached. Ultimately, the use of methyl p-bromomethylbenzoate in the presence of potassium hydride and 18-crown-6 furnished the hinge part of 6.
21. 1-3: Gly, D- and L-Ala, D- and L-Val, D- and L-Leu, D- and L-Phe, D- and L-Pro, D- and L-Ser, D- and L-Thr, D- and L-Asn, D- and L-Gln, D- and L-Asp, D- and L-Glu, D- and L-His, D- and L-Lys, D- and L-Arg.
22. We attempted to reach a concentration of the receptor slightly lower than that required for binding approximately 1% of the library beads. These concentrations are listed in Table 1.
23. A bissulfonamide derivative of the diazabicyclonane system gave rise to a chair-boat shape, whereas a bistrifluoroacetyl derivative gave rise to a chair-chair shape: P. H. McCabe, N. J. Milne, G. A. Sim, J. Chem. Soc. Chem. Commun. 1985, 625-626
24. M. H. J. Ohlmeyer, R. N. Swanson, L. W. Dillard, J. C. Reader, G. Asouline, R. Kobayashi, M. Wigler, W. C. Still, Proc. Natl. Acad. Sci. USA 1993, 90, 10922-10926.