Synthesis of 2-deoxy-2-C-alkylglucosides of myo-inositol as possible inhibitors of a N-deacetylase enzyme in the biosynthesis of mycothiol

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 12, 2003, Pages 2045-2049

  Gammon, David W ^a   Hunter, Roger ^a   Steenkamp, Daniel J ^a   Mudzunga, Theophilus T ^a  

^a UNIVERSITY OF CAPE TOWN   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

1 DEXTRO 1 O (2 ACETAMIDO 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSYL)INOSITOL; 1 DEXTRO 1 O [(2C ALLYL 2 DEOXY) DEXTRO GLUCOPYRANOSYL]INOSITOL; 2 C ALLYL 2 DEOXYGLUCOSYLFLUORIDE; 2 DEOXY 2 C (2' HYDROXYPROPYL) DEXTRO GLUCOSIDE; 2 DEOXY 2 C (2' OXOPROPYL) DEXTRO GLUCOSIDE; BENZYL DERIVATIVE; ENZYME; ENZYME INHIBITOR; FLUORIDE; GLUCOSIDE; INOSITOL; MYCOTHIOL; N DEACETYLASE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL CELL; BIOSYNTHESIS; DRUG SYNTHESIS; METABOLITE; MYCOBACTERIUM; MYCOBACTERIUM SMEGMATIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PROTEIN ASSEMBLY;

CORYNEBACTERINEAE; MYCOBACTERIUM; MYCOBACTERIUM SMEGMATIS;

EID: 0037763888     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00157-4     Document Type: Article

References (26)

1. Newton G.L., Arnold K., Price M.S., Sherrill C., Delcardayere S.T., Aharonowitz Y., Cohen G., Davies J., Fahey R.C., Davis C. J. Bacteriol. 178:1996;1990 Newton G.L., Av-Gay Y., Fahey R.C. Biochemistry. 39:2000;10739.
2. Newton G.L., Arnold K., Price M.S., Sherrill C., Delcardayere S.T., Aharonowitz Y., Cohen G., Davies J., Fahey R.C., Davis C. J. Bacteriol. 178:1996;1990 Newton G.L., Av-Gay Y., Fahey R.C. Biochemistry. 39:2000;10739.
3. Rawat M., Newton G.L., Ko M., Martinez G.J., Fahey R.C., Av-Gay Y. Antimicrob. Agents Chemother. 46:2002;3348.
4. Sakuda S., Zhou Z.Y., Yamada Y. Biosci. Biotech. Biochem. 58:1994;1347.
5. Spies H.S.C., Steenkamp D.J. Eur. J. Biochem. 224:1994;203.
6. Jardine M.A., Spies H.S.C., Nkambule C.M., Gammon D.W., Steenkamp D.J. Biorg. Med. Chem. 10:2002;875.
7. Nicholas G.N., Kovác P., Bewley C.A. J. Am. Chem. Soc. 124:2002;3492.
8. Bornemann C., Jardine M.A., Spies H.S.C., Steenkamp D.J. Biochem. J. 325:1997;623.
9. (a) Lindberg J., Öhberg L., Garregg P.J., Konradsson P. Tetrahedron. 58:2002;1387.
10. (b) Martín-Lomas M., Flores-Mosquera M., Chiara J.L. Eur. J. Org. Chem. 2000;1547.
11. (c) Madsen R., Udodong U.E., Roberts C., Mootoo D.R., Konradsson P., Fraser-Reid B. J. Am. Chem. Soc. 117:1995;1554.
12. Pietrusiewicz K.M., Salamoñczyk G.M., Bruzik K.S. Tetrahedron. 48:1992;5523.
13. Massy D.J., Wyss P. Helv. Chim. Acta. 73:1990;1037.
14. Vacca P.P., deSolms J., Huff J.R. J. Am. Chem. Soc. 109:1987;3478.
15. Shvets V.I., Klyashchitskii B.A., Stepanov A.E., Evstigneeva R.P. Tetrahedron. 29:1973;331.
16. Hang H.C., Bertozzi C.R. J. Am. Chem. Soc. 123:2001;1242.
17. Excoffier G., Gagnaire D., Utille J. Carbohydr. Res. 39:1975;368.
18. Posner G.H., Haines S.R. Tetrahedron Lett. 26:1985;5.
19. (a) Elie C.J.J., Dreef C.E., Verduyn R., Van der Marel G.A., Van Boom J.H. Tetrahedron. 45:1989;3477.
20. (b) Kunz H., Sager W. Helv. Chim. Acta. 68:1985;283.
21. (a) Giese, B. Radical in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Elmsford, 1986.
22. (b) Korth H., Sustmann R., Giese B., Rücker B., Gröninger K.S. Chem. Ber. 123:1990;1891.
23. (a) Imuta M., Ziffer H. J. Org. Chem. 44:1979;1351.
24. (b) Chiappe C., Crotti P., Menichetti E. Tetrahedron: Asymmetry. 9:1998;4079.
25. Trevoy L.W., Brown W.G. J. Am. Chem. Soc. 71:1949;1675.
26. Ley S.V., Norman J., Griffith W.P., Marsden P. Synthesis. 1994;639.