Generation of C-glycoside peptide ligands for cell surface carbohydrate receptors using a four-component condensation on solid support

Journal of Organic Chemistry

Volumn 61, Issue 23, 1996, Pages 8350-8354

  Sutherlin, Daniel P ^a   Stark, Todd M ^a   Hughes, Robert ^a   Armstrong, Robert W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE;

ARTICLE; DRUG SYNTHESIS;

EID: 0029801847     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960119j     Document Type: Article

References (49)

1. (a) Varki, A. Glycobiology 1993, 3, 97-130.
2. (b) Feizi, T. Curr. Opin. Struct. Bio. 1993, 3, 701.
3. (c) Varki, A. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 7390.
4. (a) Butcher, E. C. Am. J. Path. 1990, 1, 3-11.
5. (b) Walz, G.; Aruffo, A.; Kolanus, W.; Polley, M. J.; Phillips, M. L.; Wagner, E.; Nudelman, E.; Sinhal, A. K.; Hakomori, S.; Paulson, J. C. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 6224.
6. (a) Phillips, M. L.; Nudelman, E.; Gaeta, F. C. A.; Perez, M.; Sinhal, A. K.; Hakomori, S.; Paulson, J. C. Science 1990, 250, 1130.
7. (b) Higashi, H.; Hirabayashi, Y.; Fukui, Y.; Naiki, M.; Matsumoto, M.; Ueda, S.; Kato, S. Cancer Res. 1985, 45, 3796-3802.
8. (a) Paulson, J. C. The Receptors; Academic: New York, 1985; Vol. 2.
9. (b) Wharton, S. A.; Weis, W.; Skehel, J. J.; Wiley, D. C. The Influenza Virus; Plenum: New York, 1989.
10. (a) Gyler, M.; Rose, D.; Bundle, D. Science 1991, 253, 442.
11. (b) Boren, T.; Falk, P.; Roth, K. A.; Larson, G.; Normark, S. Science 1993, 262, 1892.
12. (a) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233-1251.
13. (b) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385-1401.
14. Ugi, I. Angew. Chem., Int. Ed. Engl. 1982, 21, 810-819.
15. (a) Ugi, I.; Dömling, A.; Hörl, W. Endeavour 1994, 18, 115-123.
16. (b) Wipf, P.; Cunningham, A. Tetrahedron Lett. 1995, 36, 7819-7822.
17. Each well contains two diastereomers.
18. (a) Kiessling, L. L.; Pohl, N. L. Chem. Biol. 1996, 3, 71.
19. (b) Nagy, J. O.; Wang, P.; Gilbert, J. H.; Schaefer, M. E.; Hill, T. G.; Callatrom, M. R.; Bednarski, M. D. J. Med. Chem. 1992, 35, 4501-4502.
20. (a) Armstrong, R. W.; Sutherlin, D. P.; Wolinski, L. Presented at the 31st Annual ACS Western Regional Meeting, San Diego, CA, October 18-21, 1995.
21. (b) Rao, N. N. Presented at the 31st Annual ACS Western Regional Meeting, San Diego, CA, October 18-21, 1995.
22. (c) Uchiyama, T.; Vassilev, V.; Kajimoto, T.; Wong, W.; Lin, C.-C.; Huang, H.; Wong, C.-H. J. Am. Chem. Soc. 1995, 117, 5396.
23. (d) Huryn, D. Presented at the 31st Annual ACS Western Regional Meeting, San Diego, CA, October 18-21, 1995.
24. (e) For a review see Bertozzi, C. R. Chem. Biol. 1995, 11, 703-708.
25. (f) Kogan, T. P.; Dupre, B.; Keller, K. M.; Scott, I. L.; Bui, H.;Market, R. V.; Beck, P. J.; Voytus, J. A.; Revelle, B. M.; Scott, D. J. Med. Chem. 1995, 38, 4976-4984.
26. (a) Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599.
27. (b) Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160.
28. Wei, A.; Boy, K. M.; Kishi, Y. J. Am. Chem. Soc. 1995, 117, 9432-9436.
29. Toone, E. J. Curr. Opin. Struct. Bio. 1994, 4, 719-728.
30. Rink, H. Tetrahedron Lett. 1987, 28, 3787.
31. (a) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123.
32. (b) Tempest, P. A.; Brown, S. D.; Armstrong, R. W. Angew. Chem., Int. Ed. Engl. 1996, 35, 640.
33. For other applications of the Ugi reaction in combinatorial chemistry developed in the Armstrong group, see: (c) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 117, 7842. (d) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 2574. (e) Strocker, A. M.; Keating, T. A.; Tempest, P. A.; Armstrong, R. W. Tetrahedron Lett. 1996, 37, 1149.
34. For other applications of the Ugi reaction in combinatorial chemistry developed in the Armstrong group, see: (c) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 117, 7842. (d) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 2574. (e) Strocker, A. M.; Keating, T. A.; Tempest, P. A.; Armstrong, R. W. Tetrahedron Lett. 1996, 37, 1149.
35. For other applications of the Ugi reaction in combinatorial chemistry developed in the Armstrong group, see: (c) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 117, 7842. (d) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 2574. (e) Strocker, A. M.; Keating, T. A.; Tempest, P. A.; Armstrong, R. W. Tetrahedron Lett. 1996, 37, 1149.
36. (a) Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383.
37. (b) Kraus, G. A.; Molina, M. T. J. Org. Chem. 1988, 53, 752.
38. (c) Lewis, M. D.; Cha, J. K.; Kishi, Y. K J. Am. Chem. Soc. 1982, 704, 4976.
39. (a) Walborski, H. M.; Gawronska, K.; Gawronski, J. K. J. Am. Chem. Soc. 1987, 109, 6719.
40. (b) Hillis, L. R.; Ronald, R. C. J. Org. Chem. 1985, 50, 470.
41. The synthesis of the glucose version of 3 is outlined in Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743.
42. Bertozzi, C. R.; Hoeprich, P. D. Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092.
43. Yields are as follows: entry 1, R = Bn, 56%; R = Ac, 77%; entry 2, 54%; entry 3, 33%; entry 4, 17%; entry 5, 71.5%; entry 6, 56%; entry 7, 65%; entry 8, 24%; entry 9, 53% yield.
44. In all cases the equivalency of the resisn bound amine was determined by the loading level indicated by the manufacturer in mmol/g.
45. The product from entry 3 was found be 85% pure with excess napthyl peaks in the NMR, most likely due to insufficient rinsing of the pollymer suport.
46. Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press: New York, Oxford, 1989.
47. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley-Interscience: New York, 1991.
48. This caused some methyl ester formation of the free acid from concentration of TFA and methanol. In subsequent experiments this methanol wash was deleted from the procedure.
49. 1H NMR and mass spectra) of compounds from eight larger scale reactions. (Bd6) 17.4 mg, 55.8% yield; (Bh4) 14.0 mg, 47.4% yield; (Bd4) 11.0 mg, 38.0% yield; (Bf6) 9.1 mg, 32.3% yield; (Bh1) 5.0 mg, 17.4% yield; (Bb1) 8.7 mg, 28.4% yield; (Bg5) 9.7 mg, 31.6% yield; (Bg4) 2.6 mg, 9.0% yield.