Synthesis of a C-glycoside analogue of β-D-galactosyl hydroxynorvaline and its use in immunological studies

Angewandte Chemie (International Edition in English)

Volumn 39, Issue 22 SUPPL., 2000, Pages 272-280

  Wellner, Eric ^a   Gustafsson, Tomas ^a   Bäcklund, Johan ^b   Holmdahl, Rikard ^b   Kihlberg, Jan ^a  

^a UMEÅ UNIVERSITY   (Sweden)

^b LUND UNIVERSITY   (Sweden)

Author keywords

Glycopetides; Glycosides; Immunochemistry; molecular recognition; Rheumatoid Arthritis

Indexed keywords

COLLAGEN TYPE 2; DRUG DERIVATIVE; EPITOPE; GALACTOSE; GLYCOPEPTIDE; HLA ANTIGEN; INTERLEUKIN 2; LIGAND; VALINE;

ANIMAL; ARTHRITIS; ARTICLE; C3H MOUSE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DBA MOUSE; GLYCOSYLATION; HYBRIDOMA; IMMUNOLOGY; METABOLISM; MOUSE; RAT; RHEUMATOID ARTHRITIS; SYNTHESIS; T LYMPHOCYTE;

ANIMALS; ARTHRITIS, EXPERIMENTAL; ARTHRITIS, RHEUMATOID; CARBOHYDRATE CONFORMATION; COLLAGEN TYPE II; GALACTOSE; GLYCOPEPTIDES; GLYCOSYLATION; HLA ANTIGENS; HYBRIDOMAS; IMMUNODOMINANT EPITOPES; INTERLEUKIN-2; LIGANDS; MICE; MICE, INBRED C3H; MICE, INBRED DBA; MOLECULAR STRUCTURE; RATS; T-LYMPHOCYTES; VALINE;

EID: 0039174266     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (67)

1. K. I. Kivirikko, R. Myllylä in Post-translationalmodifications (Eds.: J. B. Weiss, M. I. V. Jayson), Churchill Livingstone, Edinburgh, 1982, pp. 101-120.
2. R. G. Spiro, J. Biol. Chem. 1967, 242, 4813-4823.
3. a) M. A. Cremer, E. F. Rosloniec, A. H. Kang, J. Mol. Med 1998, 76, 275-288;
4. b) R. Holmdahl, E. C. Andersson, C. B. Anderssen, A. Svejgaard, L. Fugger, lmmunol. Rev. 1999, 169, 161-173.
5. a) E. Michaëlsson, M. Andersson, Å. Engström, R. Holmdahl, Eur. J. Immunol. 1992, 22, 1819-1825;
6. b) E. Michaëlsson, V. Malmström, S. Reis, Å. Engström, H. Burkhardt, R. Holmdahl, J. Exp. Med. 1994, 180, 745-749.
7. a) J. Broddefalk, J. Bäcklund, F. Almqvist, M. Johansson, R. Holmdahl, J. Kihlberg, J. Am. Chem. Soc. 1998, 120, 7676-7683;
8. b) A. Corthay, J. Bäcklund, J. Broddefalk, E. Michaëlsson, T. J. Goldschmidt, J. Kihlberg, R. Holmdahl, Eur. J. lmmunol. 1998, 28, 2580-2590;
9. c) P. Kjellén, U. Brunsberg, J. Broddefalk, B. Hansen, M. Vestberg, I. Ivarsson, Å. Engström, A. Svejgaard, J. Kihlberg, L. Fugger, R. Holmdahl, Eur. J. Immunol. 1998, 28, 755-767.
10. P. Kjellén, U. Brunsberg, J. Broddefalk, B. Hansen, M. Vestberg, I. Ivarsson, Å. Engström, A. Svejgaard, J. Kihlberg, L. Fugger, R. Holmdahl, Eur. J. Immunol. 1998, 28, 755-767.
11. L. J. Stern, J. H. Brown, T. S. Jardetzky, J. C. Gorga, R. G. Urban, J. L. Strominger, D. C. Wiley, Nature 1994, 368, 215-221.
12. E. L. Reinherz, K. Tan, L. Tang, P. Kern, J.-h. Liu, Y. Xiong, R. E. Hussey, A. Smolyar, B. Hare, R. Zhang, A. Joachimiak, H.-C. Chang, G. Wagner, J.-h. Wang, Science 1999, 286, 1913-1921.
13. a) L. B. Nicholson, J. M. Greer, R. A. Sobel, M. B. Lees, V. K. Kuchroo, Immunity 1995, 3, 397-405;
14. b) S. Brocke, K. Gijbels, M. Allegretta, I. Ferber, C. Piercy, T. Blankenstein, R. Martin, U. Utz, N. Karin, D. Mitchell, T. Veromaa, A. Waisman, A. Gaur, P. Conion, N. Ling, P. J. Fairchild, D. C. Wraith, A. O'Garra, C. G. Fathman, L. Steinman, Nature 1996, 379, 343-346.
15. a) J. Sloan-Lancaster, P. M. Allen, Annu. Rev. Immunol. 1996, 14, 1-27;
16. b) G. J. Kersh, E. N. Kersh, D. H. Fremont, P. M. Allen, Immunity 1998, 9, 817-826.
17. Selected references: a) C. R. Bertozzi, P. D. Hoeprich, Jr., M. D. Bednarski, J. Org. Chem. 1992, 57, 6092-6094;
18. b) S. D. Debenham, J. S. Debenham, M. J. Burk, E. J. Toone, J. Am. Chem. Soc. 1997, 119, 9897-9898;
19. c) L. Lay, M. Meldal, F. Nicotra, L. Panza, G. Russo, Chem. Commun. 1997, 1469-1470;
20. d) F. Burkhart, M. Hoffmann, H. Kessler, Angew. Chem. 1997, 109, 1240-1241; Angew. Chem. Int. Ed. Engl. 1997, 36, 1191-1192;
21. d) F. Burkhart, M. Hoffmann, H. Kessler, Angew. Chem. 1997, 109, 1240-1241; Angew. Chem. Int. Ed. Engl. 1997, 36, 1191-1192;
22. e) T. Fuchs, R. R. Schmidt, Synthesis 1998, 753-758;
23. f) R. N. Ben, A. Orellana, P. Arya, J. Org. Chem. 1998, 63, 4817-4820;
24. g) D. Urban, T. Skrydstrup, J.-M. Beau, Chem. Commun. 1998, 955-956;
25. h) A. Dondoni, D. Perrone, E. Turturici, J. Org. Chem. 1999, 64, 5557-5564;
26. A. Dondoni, A. Marra, A. Massi, J. Org. Chem. 1999, 64, 933-944;
27. j) A. J. Pearce, S. Ramaya, S. N. Thorn, G. B. Bloomberg, D. S. Walter, T. Gallagher, J. Org. Chem. 1999, 64, 5453-5462;
28. k) A. D. Campbell, D. E. Paterson, T. M. Raynham, R. J. K. Taylor, Chem. Commun. 1999, 1599-1600.
29. a) C. R. Bertozzi, D. G. Cook, W. R. Kobertz, F. Gonzalez-Scarano, M. D. Bednarski, J. Am. Chem. Soc 1992, 114, 10 639-10 641;
30. b) L.-X. Wang, M. Tang, T. Suzuki, K. Kitajima, Y. Inoue, S. Inoue, J.-Q. Fan, Y. C. Lee, J. Am. Chem. Soc. 1997, 119, 11 137-11 146.
31. a) P. G. Goekjian, T.-C. Wu, Y. Kishi, J. Org. Chem. 1991, 56, 6412-6422;
32. b) P. G. Goekjian, T.-C. Wu, H.-Y. Kang, Y. Kishi, J. Org. Chem. 1991, 56, 6422-6434;
33. c) Y. Wang, P. G. Goekjian, D. M. Ryckman, W. H. Miller, S. A. Babirad, Y. Kishi, J. Org. Chem. 1992, 57, 482-489;
34. d)T. Haneda, P. G. Goekjian, S. H. Kim, Y. Kishi, J. Org. Chem. 1992, 57, 490-498.
35. E. Michaëlsson, J. Broddefalk, Å. Engström, J. Kihlberg, R. Holmdahl, Eur. J. Immunol. 1996, 26, 1906-1910.
36. P. Garner, J. M. Park, J. Org. Chem. 1987, 52, 2361-2364.
37. a) A. McKillop, R. J. K. Taylor, R. J. Watson, N. Lewis, Synthesis 1994, 31-33;
38. b) A. Dondoni, D. Perrone, Synthesis 1997, 527-529.
39. a) W. M. Best, V. Ferro, J. Harle, R. V. Stick, D. M. G. Tilbrook, Aust. J. Chem. 1997, 50, 463-472;
40. b) M. D. Lewis, J. K. Cha, Y. Kishi, J. Am. Chem. Soc. 1982, 104, 4976-4978.
41. A. Dondoni, M.-C. Scherrmann, J. Org. Chem. 1994, 59, 6404-6412.
42. The conformation of lactone 7 was determined by using semi-empirical PM3 calculations. Atoms O-1, C-1, C-2, C-3, C-5, and O-5 are embedded in a plane with an average deviation of 0.022 Å. Atom O-2 points below this plane.
43. M. P. Doyle, D. J. DeBruyn, D. A. Kooistra, J. Am. Chem. Soc. 1972, 94, 3659-3661.
44. L. A. Flippin, D. W. Gallagher, K. Jalali-Araghi, J. Org. Chem. 1989, 54, 1430-1432.
45. P. J. Garegg, B. Samuelsson, J. Chem. Soc. Perkin Trans. 1 1980, 2866-2869.
46. 13C NMR spectroscopy. On conversion of 12 into 5, the C-1 signal shifts from δ=7.3 in iodide 12 to δ=22.7 in phosphonium salt 5.
47. a) R. S. Dewey, E. E. van Tamelen, J. Am. Chem. Soc. 1961, 83, 3729;
48. b) D. J. Hart, W.-P. Hong, L-Y. Hsu, J. Org. Chem. 1987, 52, 4665-4673.
49. R. C. Bernotas, R. V. Cube, Synth. Commun. 1990, 20, 1209-1212.
50. Reviewed in: a) M. Meldal in Glycopeptide synthesis (Eds.: Y. C. Lee, R. T. Lee), Academic Press, San Diego, 1994, pp. 145-198;
51. b) G. Arsequell, G. Valencia, Tetrahedron: Asymmetry 1997, 8, 2839-2876;
52. c) J. Kihlberg, M. Elofsson, Curr. Med. Chem. 1997, 4, 79-110.
53. a) N. Fujii, A. Otaka, O. Ikemura, K. Akaji, S. Funakoshi, Y. Hayashi, Y. Kuroda, H. Yajima, J. Chem. Soc. Chem. Commun. 1987, 274-275;
54. b) Y. Nakahara, Y. Nakahara, Y. Ito, T. Ogawa, Carbohydr. Res. 1998, 309, 287-296.
55. The remaining nine hybridomas either recognized peptide Cll(256-270) or modifications which had Hyl or α-D-Glc-(1 →2)-β-D-Gal-Hyl at position 264.
56. J. Broddefalk, K.-E. Bergquist, J. Kihlberg, Tetrahedron 1998, 54, 12 047-12 070.
57. S. Gillis, K. A. Smith, Nature 1977, 268, 154-156.
58. q than 1 and 3.
59. D. S. Lyons, S. A. Lieberman, J. Hampl J. J. Boniface, Y.-h. Chien, L. J. Berg, M. M. Davis, Immunity 1996, 5, 53-61.
60. a) M. D. Deck, P. Sjölin, E. R. Unanue, J. Kihlberg, J. Immunol. 1999, 162, 4740-4744;
61. b) T. Jensen, P. Hansen, L. Galli-Stampino, S. Mouritsen, K. Frische, E. Meinjohanns, M. Meldal, O. Werdelin, J. Immunol. 1997, 158, 3769-3778.
62. a) A. E. Derome, M. P. Williamson, J. Magn. Reson. 1990, 88, 177-185;
63. b) A. Bax, D. G. Davis, J. Magn. Reson. 1985, 65, 355-360;
64. c) A. Kumar, R. R.Ernst, K. Wüthrich, Biochem. Biophys. Res. Commun. 1980, 95, 1-6.
65. 20% Pd on carbon (dry basis); Degussa type E 101 NE/W.
66. 3 (1 g) to aqueous sulfuric acid (4.4M, 10 mL).
67. W. König, R. Geiger Chem. Ber. 1970, 103, 788-798.