Synthetic receptors based on peptidosulfonamide peptidomimetics

Tetrahedron Letters

Volumn 37, Issue 45, 1996, Pages 8253-8256

  Löwik, Dennis W P M ^a   Mulders, Suzanne J E ^a   Cheng, Yuan ^b   Shao, Yuefei ^b   Liskamp, Rob M J ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

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

Author keywords

[No Author keywords available]

Indexed keywords

DRUG RECEPTOR; SYNTHETIC PEPTIDE;

ARTICLE; DRUG SYNTHESIS;

EID: 0030569403     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01882-5     Document Type: Article

References (26)

1. 1. For recent reviews, see e.g. L.A. Thompson, J.A. Ellman, Chem. Rev. 1996, 96, 555; M.A. Gallop, R.W. Barrett, W.J. Dower, S.P.A. Fodor, E.M. Gordon, J. Med. Chem. 1994, 37, 1233; E.M. Gordon, R.W. Barrett, W.J. Dower, S.P.A. Fodor, M.A. Gallop, ibid. 1994, 37, 1385; N.K. Terrett, M. Gardner, D.W. Gordon, R.J. Kobylecki, J. Steele, Tetrahedron, 1995, 51, 8135.
2. 1. For recent reviews, see e.g. L.A. Thompson, J.A. Ellman, Chem. Rev. 1996, 96, 555; M.A. Gallop, R.W. Barrett, W.J. Dower, S.P.A. Fodor, E.M. Gordon, J. Med. Chem. 1994, 37, 1233; E.M. Gordon, R.W. Barrett, W.J. Dower, S.P.A. Fodor, M.A. Gallop, ibid. 1994, 37, 1385; N.K. Terrett, M. Gardner, D.W. Gordon, R.J. Kobylecki, J. Steele, Tetrahedron, 1995, 51, 8135.
3. 1. For recent reviews, see e.g. L.A. Thompson, J.A. Ellman, Chem. Rev. 1996, 96, 555; M.A. Gallop, R.W. Barrett, W.J. Dower, S.P.A. Fodor, E.M. Gordon, J. Med. Chem. 1994, 37, 1233; E.M. Gordon, R.W. Barrett, W.J. Dower, S.P.A. Fodor, M.A. Gallop, ibid. 1994, 37, 1385; N.K. Terrett, M. Gardner, D.W. Gordon, R.J. Kobylecki, J. Steele, Tetrahedron, 1995, 51, 8135.
4. 1. For recent reviews, see e.g. L.A. Thompson, J.A. Ellman, Chem. Rev. 1996, 96, 555; M.A. Gallop, R.W. Barrett, W.J. Dower, S.P.A. Fodor, E.M. Gordon, J. Med. Chem. 1994, 37, 1233; E.M. Gordon, R.W. Barrett, W.J. Dower, S.P.A. Fodor, M.A. Gallop, ibid. 1994, 37, 1385; N.K. Terrett, M. Gardner, D.W. Gordon, R.J. Kobylecki, J. Steele, Tetrahedron, 1995, 51, 8135.
5. 2. W.C. Still, Acc. Chem. Res. 1996, 29, 155.
6. 3. See e.g. K. Burgess, H-J. Lim, A.M. Porte, G.A. Sulikowski, Angew. Chem.Int. Ed. Engl. 1996, 35, 220.
7. 4. (a) W.J. Moree, G.A. van der Marel, R.M.J. Liskamp, Tetrahedron Lett. 1991, 32, 409.
8. (b) W.J. Moree, G.A. van der Marel, R.M.J. Liskamp, Tetrahedron Lett. 1992, 33, 6389.
9. (c) W.J. Moree; G.A. van der Marel; R.M.J. Liskamp, Tetrahedron 1993, 49, 1133.
10. (d) W.J. Moree, A. Schouten, J. Kroon, R.M.J. Liskamp, Int J. Pept. Prot. Res. 1995, 45, 501
11. (e) W.J. Moree, G.A. van der Marel, R.M.J. Liskamp, J. Org. Chem . 1995, 60, 5157;
12. (f) D.B.A. de Bont, W.J. Moree, R.M.J. Liskamp, Bioorganic and Med. Chem. 1996, 4, 667.
13. a-values of sulfonamides: B. Nyasse, L. Grehn, U. Ragnarsson, H.L.S. Maia, L.S. Monteiro, I. Leito, I. Koppel, J. Koppel, J. Chem. Soc. Perkin Trans. 1, 1995, 2025.
14. 6. S.C. Zimmerman, W. Wu, Z. Zeng, J. Am. Chem. Soc. 1991, 113, 196; R. Boyce, G. Li, H.P. Nestler, T. Suenaga, W.C. Still, ibid. 1994, 116, 7955; S.R. Labrenz, J.W. Kelly, ibid. , 1995, 117, 1655; Y. Cheng, T. Suenaga, W.C. Still, ibid. 1996, 118, 1813; H. Wennemers, S.S. Yoon, W.C. Still, J. Org. Chem. 1995, 60, 1108; Gennari, C.; Nestler, H.P.; Salom, B.; Still, W.C. ibid. 1995, 34, 1765.
15. 6. S.C. Zimmerman, W. Wu, Z. Zeng, J. Am. Chem. Soc. 1991, 113, 196; R. Boyce, G. Li, H.P. Nestler, T. Suenaga, W.C. Still, ibid. 1994, 116, 7955; S.R. Labrenz, J.W. Kelly, ibid. , 1995, 117, 1655; Y. Cheng, T. Suenaga, W.C. Still, ibid. 1996, 118, 1813; H. Wennemers, S.S. Yoon, W.C. Still, J. Org. Chem. 1995, 60, 1108; Gennari, C.; Nestler, H.P.; Salom, B.; Still, W.C. ibid. 1995, 34, 1765.
16. 6. S.C. Zimmerman, W. Wu, Z. Zeng, J. Am. Chem. Soc. 1991, 113, 196; R. Boyce, G. Li, H.P. Nestler, T. Suenaga, W.C. Still, ibid. 1994, 116, 7955; S.R. Labrenz, J.W. Kelly, ibid. , 1995, 117, 1655; Y. Cheng, T. Suenaga, W.C. Still, ibid. 1996, 118, 1813; H. Wennemers, S.S. Yoon, W.C. Still, J. Org. Chem. 1995, 60, 1108; Gennari, C.; Nestler, H.P.; Salom, B.; Still, W.C. ibid. 1995, 34, 1765.
17. 6. S.C. Zimmerman, W. Wu, Z. Zeng, J. Am. Chem. Soc. 1991, 113, 196; R. Boyce, G. Li, H.P. Nestler, T. Suenaga, W.C. Still, ibid. 1994, 116, 7955; S.R. Labrenz, J.W. Kelly, ibid. , 1995, 117, 1655; Y. Cheng, T. Suenaga, W.C. Still, ibid. 1996, 118, 1813; H. Wennemers, S.S. Yoon, W.C. Still, J. Org. Chem. 1995, 60, 1108; Gennari, C.; Nestler, H.P.; Salom, B.; Still, W.C. ibid. 1995, 34, 1765.
18. 6. S.C. Zimmerman, W. Wu, Z. Zeng, J. Am. Chem. Soc. 1991, 113, 196; R. Boyce, G. Li, H.P. Nestler, T. Suenaga, W.C. Still, ibid. 1994, 116, 7955; S.R. Labrenz, J.W. Kelly, ibid. , 1995, 117, 1655; Y. Cheng, T. Suenaga, W.C. Still, ibid. 1996, 118, 1813; H. Wennemers, S.S. Yoon, W.C. Still, J. Org. Chem. 1995, 60, 1108; Gennari, C.; Nestler, H.P.; Salom, B.; Still, W.C. ibid. 1995, 34, 1765.
19. 6. S.C. Zimmerman, W. Wu, Z. Zeng, J. Am. Chem. Soc. 1991, 113, 196; R. Boyce, G. Li, H.P. Nestler, T. Suenaga, W.C. Still, ibid. 1994, 116, 7955; S.R. Labrenz, J.W. Kelly, ibid. , 1995, 117, 1655; Y. Cheng, T. Suenaga, W.C. Still, ibid. 1996, 118, 1813; H. Wennemers, S.S. Yoon, W.C. Still, J. Org. Chem. 1995, 60, 1108; Gennari, C.; Nestler, H.P.; Salom, B.; Still, W.C. ibid. 1995, 34, 1765.
20. 7. S.J.E. Mulders, A.J. Brouwer, P. Van Den Meer, R.M.J. Liskamp, manuscript in preparation .
21. 8. Procedure: see reference 4c.
22. +: m/z 1345.3
23. 10. Oxidation of diazo compounds see e.g. : J. Muzart, Synthesis, 1995, 1325.
24. 11. 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.
25. 12. The sequences found by decoding the beads where: (D)Glu-(D)Phe-(D)Asn (1x); (D)Pro-(L)Asp-(L)His (3x); (D)Val-(D)Asp-(D)Asp(1x); (D)Val-(L)Asp-(L)Asp (1x); (D)Ala-(L)Asp-(D)Asn (4x); (D)Ala-(L)Asp-(D)His (2x); (D)Ala-(L)Asp-(D)Ser (4x); (D)Ala-(L)Asp-(D)Thr (1x); Gly-(D)His-(D)Asp (1x); Gly-(L)Asp-(L)Asp (1x); Gly-(L)Asn-(L)Asp (1x); (L)Glu-(D)Asn-(L)Val (2x); (L)Glu-(D)HiS-(D)Glu (1x); (L)Glu-(D)His-(L)Asn (1x); (L)Glu-(D)His-(L)Val (1x); (L)Glu-(L)Asn-(L)Asn (1x); (L)Glu-(L)Asn-(L)Leu (1x); L)Ala-(D)Asp-(L)Asn (2x); (L)Ala-(D)Asp-(L)Asp (2x); (L)Ala-(D)Asp-(L)Val (1x); (L)Ala-(D)Asp-(L)Ser (1x); (L)Pro-(L)Glu-(L)Pro (1x).
26. 13. For a recent example of hydrogen bonding between a sulfonamide and a carboxylic acid in the solid-state, see: M.R. Caira, L.R. Nassimbem, A.F. Wildervanck, J.Chem. Soc. Perkin Trans. 2 , 1995, 2213.