Chemoenzymatic synthesis of neuraminic acid analogs structurally varied at C-5 and C-9 as potential inhibitors of the sialidase from influenza virus

Carbohydrate Research

Volumn 280, Issue 1, 1996, Pages 101-110

  Murakami, Makoto ^a   Ikeda, Kiyoshi ^a   Achiwa, Kazuo ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

influenza virus; inhibitors; Neu5Ac aldolase; neuraminic acid analogs; sialidases

Indexed keywords

ANTIVIRUS AGENT; NEURAMINIC ACID DERIVATIVE; SIALIDASE; SIALIDASE INHIBITOR;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; ENZYME INHIBITION; INFLUENZA VIRUS; PRIORITY JOURNAL;

EID: 0030040371     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/0008-6215(95)00295-2     Document Type: Article

References (15)

1. (a) A.K.J. Chong, M.S. Pegg, N.R. Taylor, and M. von Itzstein, Eur. J. Biochem., 207 (1992) 335-345;
2. (b) N.R. Taylor and M. von Itzstein, J. Med. Chem., 27 (1994) 616-624;
3. (c) G. Herrler, A. Imhof, R. Brossmer, G. Milks, and J.C. Paulson, J. Biol. Chem., 267 (1992) 12501-12505.
4. (a) P. Meindl, G. Bodo, P. Palese, J. Schulman, and H. Tuppy, Virology, 58 (1974) 457-463;
5. (b) P.-A. Driguez, B. Barrere, G. Quash, and A. Doutheau, Carbohydr. Res., 262 (1994) 297-310;
6. (c) T. Hagiwara, I. Kijima-Suda, T. Ido, H. Ohrui, and K. Tomota, Carbohydr. Res., 263 (1994) 167-172.
7. M. von Itzstein, W.-Y. Wu, G.B. Kok, M.S. Pegg, J.C. Dyason, B. Jin, T.V. Phan, M.L. Smythe, H.F. White, S.W. Oliver, P.M. Colman, J.N. Varghese, D.M. Ryan, J.M. Woods, R.C. Bethell, V.J. Hotham, J.M. Cameron, and C.R. Penn, Nature, 363 (1993) 418-423.
8. W.P. Burmeister, R.W.H. Ruigrok, and S. Cusack, EMBO J., 11 (1992) 49-56.
9. (a) M.A. Sparks, K.W. Williams, C. Lukacs, A. Schrell, G. Priebe, A. Spaltanstein, and G.M. Whitesides, Tetrahedron, 49 (1993) 1-12.
10. (b) J.L.-C. Liu, G.-J. Shen, Y. Ichikawa, J.F. Rutan, G. Zapata, W.F. Wann, and C.-H. Wong, J. Am. Chem. Soc., 114 (1992) 3901-3910.
11. Dominicus J.M. van der Vliugel, W.A.R. van Heeswijk, and J.F.G. Vliegenthart, Carbohydr. Res., 102 (1982) 121.
12. Y. Kiso, K. Ukawa, and T. Akita, J. Chem. Soc. Chem. Commun., (1980) 101-1102.
13. N.E. Byramova, A.B. Yuzikov, and N.V. Bovin, Carbohydr. Res., 237 (1992) 161-175.
14. H. Bayley, D.N. Standring, and J.R. Knowles, Tetrahedron Lett., 39 (1978) 3633-3634.
15. K. Okamoto, T. Kondo, and T. Goto, Bull. Chem. Soc. Jpn., 60 (1987) 631-636.