Synthesis and biological activity of ester and ether analogues of α-galactosylceramide (KRN7000)

Carbohydrate Research

Volumn 345, Issue 12, 2010, Pages 1663-1684

  Shiozaki, Masao ^a   Tashiro, Takuya ^a   Koshino, Hiroyuki ^a   Nakagawa, Ryusuke ^b   Inoue, Sayo ^b   Shigeura, Tomokuni ^b   Watarai, Hiroshi ^b   Taniguchi, Masaru ^b   Mori, Kenji ^a  

^a RIKEN   (Japan)

^b Institute of Physical and Chemical Research   (Japan)

Author keywords

Ester analogues of galactosylceramide; Glycolipid; Glycosylation; iNKT cells; KRN7000

Indexed keywords

AMIDE GROUPS; BIOLOGICAL ACTIVITIES; ETHER GROUP; GLYCO LIPIDS; INKT CELLS; KRN7000; METHOXY;

AMIDES; ESTERS; ETHERS; GLYCOSYLATION;

ESTERIFICATION;

1 (TERT BUTYLDIMETHYLSILYLOXY) 2 (4 METHOXYBENZYLOXY) 11 OCTADECYN 3,4 DIOL; 1 (TERT BUTYLDIMETHYLSILYLOXY) 3,4 O ISOPROPYLIDENE 11 OCTADECYN 2 OL; 1 (TERT BUTYLDIMETHYLSILYLOXY) 3,4 O ISOPROPYLIDENE 2 (4 METHOXYBENZYLOXY) 11 OCTADECYNE; 1 (TETRAHYDRO 2'H PYRAN 2' YLOXY) 6 TRIDECYNE; 1 O (ALPHA GALACTOPYRANOSYL) 2 HEXACOSANOYLAMINO 1,3,4 OCTADECANETRIOL; 1,2 DI TERT BUTYLDIMETHYLSILYLOXY 3,4 O ISOPROPYLIDENEDECAN 10 OL; 1,3 O [BENZYLIDENE] 2 (4 METHOXYBENZYLOXY) 11 OCTADECYN 4 OL; 10 BENZYLOXY 1 TERT BUTYLDIMETHYLSILYLOXY 3,4 O ISOPROPYLIDENE 5 DECENE 2 OL; 10 BENZYLOXY 1,2 DI TERT BUTYLDIMETHYLSILYLOXY 3,4 O ISOPROPYLIDENEDECENE; 10 BROMO 1,2 DI TERT BUTYLDIMETHYLSILYLOXY 3,4 O ISOPROPYLIDENEDECANE; 2 (4 METHOXYBENZYLOXY) 11 OCTADECYN 1,3,4 TRIOL; 2 BENZOYLOXY 1 (TERT BUTYLDIMETHYLSILYLOXY) 3,4 O ISOPROPYLIDENE 11 OCTADECYNE; 2 HEXACOSANOYLOXY 3 HYDROXY 4 METHOXYOCTADECYL ALPHA DEXTRO GALACTOPYRANOSIDE; 2 HEXACOSANOYLOXY 3,4 DIHYDROXY 11 OCTADECYNYL ALPHA DEXTRO GALACTOPYRANOSIDE; 2 HEXACOSANOYLOXY 3,4 DIHYDROXYOCTADECYL ALPHA DEXTRO GALACTOPYRANOSIDE; 2 HEXACOSANOYLOXY 3,4 O ISOPROPYLIDENE 11 OCTADECYNYL 4,6 O BENZYLIDENE 2,3 DI O (4 METHOXYBENZYL)ALPHA DEXTRO GALACTOPYRANOSIDE; 2 HEXACOSANOYLOXY 3,4 O ISOPROPYLIDENE 11 OCTADECYNYL 4,6 O BENZYLIDENE ALPHA DEXTRO GALACTOPYRANOSIDE; 2 HEXACOSYLOXY 3,4 O ISOPROPYLIDENE 11 OCTADECYNYL 4,6 O BENZYLIDENE 2,3 DI O (4 METHOXYBENZYL)ALPHA DEXTRO GALACTOPYRANOSIDE; 2 HYDROXY 3,4 O ISOPROPYLIDENE 11 OCTADECYNYL 4,6 O BENZYLIDENE 2,3 DI O (4 METHOXYBENZYL)ALPHA DEXTRO GALACTOPYRANOSIDE; 2 HYDROXY 3,4 O ISOPROPYLIDENE 11 OCTADECYNYL 4,6 O BENZYLIDENE 2,3 DI O (4 METHOXYBENZYL)BETA DEXTRO GALACTOPYRANOSIDE; 3,4 DIHYDROXY 2 HEXACOSANOYLOXYOCTADECYL 6 OMETHYL ALPHA DEXTRO GALACTOPYRANOSIDE; 3,4 DIHYDROXY 2 HEXACOSYLOXY 1 OCTADECYL ALPHA DEXTRO GALACTOPYRANOSIDE; 3,4 DIHYDROXY 2 HEXACOSYLOXY 11 OCTADECYNYL ALPHA DEXTRO GALACTOPYRANOSIDE; 3,4 O ISOPROPYLIDENE 11 OCTADECYN 1,2 DIOL; 4 HEXACOSANOYLOXY 2,3 DIHYDROXY 11 OCTADECYNYL ALPHA DEXTRO GALACTOPYRANOSIDE; 4 METHYLPHENYL 4,6 O BENZYLIDENE 2,3 DI O (4 METHOXYBENZYL) 1 THIO BETA DEXTRO GALACTOPYRANOSIDE; 4,5 ANHYDRO 1,3 O BENZYLIDENE 2 O (4 METHOXYBENZYL)DEXTRO ARABINITOL; 4,6O BENZYLIDENE 2,3 DI O (4 METHOXYBENZYL)ALPHA,BETA DEXTRO GALACTOPYRANOSE; TRICHLOROACETIMIDOYL 4,6 O BENZYLIDENE 2,3 DI O (4 METHOXYBENZYL) ALPHA DEXTRO GALACTOPYRANOSIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL CELL; ARTICLE; CELL ACTIVATION; DRUG ACTIVITY; DRUG SYNTHESIS; MOUSE; NATURAL KILLER T CELL; NONHUMAN; PRIORITY JOURNAL; PROTEIN SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANIMALS; ESTERS; ETHERS; GALACTOSYLCERAMIDES; INTERFERON-GAMMA; INTERLEUKIN-4; MICE; MOLECULAR CONFORMATION; NATURAL KILLER T-CELLS; STEREOISOMERISM;

EID: 77955653859     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2010.05.003     Document Type: Article

References (34)

1. T. Natori, Y. Koezuka, and T. Higa Tetrahedron Lett. 34 1993 5591 5592
2. K. Akimoto, T. Natori, and M. Morita Tetrahedron Lett. 35 1994 5593 5596
3. T. Natori, M. Morita, K. Akimoto, and Y. Koezuka Tetrahedron 50 1994 2771 2784
4. M. Morita, K. Motoki, K. Akimoto, T. Natori, T. Sakai, E. Sawa, K. Yamaji, Y. Koezuka, E. Kobayashi, and H. Fukushima J. Med. Chem. 38 1995 2176 2187
5. T. Kawano, J. Cui, Y. Koezuka, I. Toura, Y. Kaneko, K. Motoki, H. Ueno, R. Nakagawa, H. Sato, E. Kaneko, H. Koseki, and M. Taniguchi Science 278 1997 1626 1629
6. Z. Zeng, A.R. Castano, B.W. Segelke, E.A. Stura, P.A. Peterson, and I.A. Wilson Science 277 1997 339 345
7. D.M. Zajonc, C. Cantu III, J. Mattner, D. Zhou, P.B. Savage, A. Bendelac, I.A. Wilson, and L. Tayton Nat. Immunol. 6 2005 810 818
8. M. Koch, V.S. Stronge, D. Shepherd, S.D. Gadola, B. Mathew, G. Ritter, A.R. Fersht, G.S. Besra, R.R. Schmidt, E.Y. Jones, and V. Cerundolo Nat. Immunol. 6 2005 819 826
9. N.A. Borg, K.S. Wun, L. Kjer-Nielsen, M.C.J. Wilce, D.G. Pellicci, R. Koh, G.S. Besra, M. Bharadwaj, D.I. Godfrey, J. McCluskey, and J. Rossjohn Nature 448 2007 44 49
10. G. Yang, J. Schmieg, M. Tsuji, and R.W. Franck Angew. Chem., Int. Ed. 43 2004 3818 3822
11. G. Chen, J. Schmieg, M. Tsuji, and R.W. Franck Org. Lett. 6 2004 4077 4080
12. R.W. Franck, and M. Tsuji Acc. Chem. Res. 39 2006 692 701
13. P. Wipf, and J.G. Pierce Org. Lett. 8 2006 3375 3378
14. T. Tashiro, R. Nakagawa, T. Hirokawa, S. Inoue, H. Watarai, M. Taniguchi, and K. Mori Tetrahedron Lett. 48 2007 3343 3347
15. T. Tashiro, R. Nakagawa, S. Inoue, M. Shiozaki, H. Watarai, M. Taniguchi, and K. Mori Tetrahedron Lett. 49 2008 6827 6830
16. M. Trappeniers, K. Van Beneden, T. Decruy, U. Hillaert, B. Linclau, D. Elewaut, and S. Van Calenbergh J. Am. Chem. Soc. 130 2008 16468 16469
17. M. Shiozaki, H. Doi, D. Tanaka, T. Shimozato, and S. Kurakata Bioorg. Med. Chem. 14 2006 3011 3016
18. Christ, W. J.; Rossignol, D. P.; Kobayashi, S.; Kawata, T. U.S. Patent 5,935,938, 1999.
19. O. Plettenburg, V. Bodmer-Narkevitch, and C.-H. Wong J. Org. Chem. 67 2002 4559 4564
20. K. Murata, T. Toba, K. Nakanishi, B. Takahashi, T. Yamamura, S. Miyake, and H. Annoura J. Org. Chem. 70 2005 2398 2401
21. J. Müller, M. Brunnbauer, M. Schmidt, A. Zimmermann, and A. Terfort Synthesis 2005 998 1004
22. H.R. Moon, W.J. Choi, H.O. Kim, and L.S. Jeong Tetrahedron: Asymmetry 13 2002 1189 1193
23. Y.V. Mahidhar, M. Rajesh, and A. Chaudhuri J. Med. Chem. 47 2004 3938 3948
24. H. Fujishima, H. Takeshita, S. Suzuki, M. Toyota, and M. Ihara J. Chem. Soc., Perkin Trans. 1 1999 2609 2616
25. Review: A. Imamura, H. Ando, H. Ishida, and M. Kiso Heterocycles 76 2008 883 908
26. Existence of this type of silanols has already been reported: J. Van der Eycken, and M. Vandewalle Tetrahedron 42 1986 4297 4308
27. M. Yu, and B.L. Pagenkopf J. Org. Chem. 67 2002 4553 4558
28. N. Matsumori, D. Kaneno, M. Murata, H. Nakamura, and H. Tachibana J. Org. Chem. 64 1999 866 876
29. S. Buchini, and C.J. Leumann Eur. J. Org. Chem. 2006 3152 3168
30. G. Parmentier, G. Schmitt, F. Dolle, and B. Luu Tetrahedron 50 1994 5361 5368
31. R.M. Ndonye, D.P. Izmirian, M.F. Dunn, K.O.A. Yu, S.A. Porcelli, A. Khurana, M. Kronenberg, S.K. Richardson, and A.R. Howell J. Org. Chem. 70 2005 10260 10270
32. T.W. Ku, M.E. McCarthy, B.M. Weichman, and J.G. Gleeson J. Med. Chem. 28 1985 1847 1853
33. W. Hakamata, T. Nishio, R. Sato, T. Mochizuki, K. Tsuchiya, M. Yasuda, and T. Oku J. Carbohydr. Chem. 19 2000 359 377
34. E. Morgan, R. Varro, H. Sepulveda, J.A. Ember, J. Apgar, J. Wilson, L. Lowe, R. Chen, L. Shivraj, A. Agadir, R. Campos, D. Ernst, and A. Gaur Clin. Immunol. 110 2004 252 266