Synthesis of GLA-60 positional isomer as an LPS-agonist and its activity

Chemistry Letters

Volumn , Issue 9, 1996, Pages 735-736

  Shiozaki, Masao ^a   Arai, Masami ^a   Macindoe, Wallace M ^a   Mochizuki, Takashi ^a   Kurakata, Shin Ichi ^a   Maeda, Hiroaki ^a   Nishijima, Masahiro ^b  

^a DAIICHI SANKYO CO   (Japan)

^b NATIONAL INSTITUTE OF INFECTIOUS DISEASES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030371209     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.735     Document Type: Article

References (17)

1. O. Westphal and O. Luderitz, Angew. Chem., 66, 407 (1954).
2. M. Imoto, H. Yoshimura, N. Sakaguchi, S. Kusumoto, and T. Shiba, Tetrahedron Lett., 26, 1545 (1985).
3. S. Takahashi, S. Nakamoto, K. Ikeda, and K. Achiw, Tetrahedron Lett., 27, 1819 (1986).
4. a) H. Paulsen and C. Krogmann, Carbohydr. Res., 205, 31, (1990);
5. b) H. Paulsen and E. C. Hoffgen, Tetrahedron Lett., 32, 2747 (1991);
6. c) H. Paulsen and M. Brenken, Liebigs Ann. Chem., 1991, 1113;
7. d) E. Katzenellenbogen, A. Gamian, E. Romanowska, U. Dabrowski, and J. Dabrowski, Eur. J. Biochem., 196, 197 (1991);
8. e) M. B. Perry and M. M. MacLeen, Carbohydr. Res., 232, 143 (1992).
9. a) M. Matsuura, Y. Kojima, J. Y. Homma, Y. Kubota, A. Yamamoto, M. Kiso, and A. Hasegawa, FEBS Lett., 167, 226 (1984);
10. b) M. Kiso, H. Ishida, and A. Hasegawa, Agric. Biol. Chem., 48, 251 (1984);
11. c) M. Kiso, S. Tanaka, M. Fujita, Y. Fujishima, Y. Ogawa, H. Ishida, and A. Hasegawa, Carbohydr. Res., 162, 127 (1987);
12. d) M. Kiso, Y. Ogawa, S. Tanaka, Y. Fujishima, M. Fujita, and A. Hasegawa, J. Carbohydr. Chem., 6, 625 (1987).
13. W. J. Christ, O. Asano, A. L. C. Robidoux, M. Perez, Y. Wang, G. R. Dubuc, W. E. Gavin, L. D. Hawkins, P. D. McGuinness, M. A. Mullarkey, D. Lewis, Y. Kishi, T. Kawata, J. R. Bristol, J. R. Rose, D. P. Rossignol, S. Kobayashi, I. Hishinuma, A. Kimura, N. Asakawa, K. Katayama, and I. Yamatsu, Science, 268, 80, (1995).
14. H. Kunz, W. Sager, D. Schanzenbach, and M. Decker, Liebigs Ann. Chem., 1991, 649.
15. a) Commercially available (R)-3-hydroxytetradecanoic acid was converted to (R)-3-tetradecanoyloxytetradecanoic acid in three steps as follows: (i) esterification of the acid with diphenyl diazomethane, (ii) acylation of the 3-hydroxy group with tetradecanoyl chloride and triethyl amine, and (iii) deprotection of the diphenylmethyl ester with trifluoroacetic acid or by hydrogenolysis.
16. b) cf. An alternative route. P. K. Jadhav, Tetrahedron Lett., 30, 4763 (1989).
17. 1-NH).