Digitoxosyltetracenomycin C and glucosyltetracenomycin C, two novel elloramycin analogues obtained by exploring the sugar donor substrate specificity of glycosyltransferase ELmGT

Journal of Natural Products

Volumn 65, Issue 11, 2002, Pages 1685-1689

  Fischer, Carsten ^a   Rodríguez, Leticia ^b   Patallo, Eugenio P ^b   Lipata, Fredilyn ^a   Braña, Alfredo F ^b   Méndez, Carmen ^b   Salas, Jose A ^b   Rohr, Jürgen ^a  

^a University of Kentucky   (United States)

^b DEPARTAMENTO DE BIOQUÍMICA Y BIOLOGÍA MOLECULAR   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

8 NOR 8 DEXTRO GLUCOSYLTETRACENOMYCIN C; 8 NOR 8 LEVO DIGITOXOSYLTETRACENOMYCIN C; 8 NORTETRACENOMYCIN C; CARBOHYDRATE DERIVATIVE; DIGITOXOSYLTETRACENOMTCIN C; ELLORAMYCIN DERIVATIVE; GLUCOSYLTETRACENOMYCIN C; GLYCOSYLTRANSFERASE; POLYKETIDE; RHAMNOSE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL GENE; BIOSYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; ELMGT GENE; ENZYME ACTIVITY; MASS SPECTROMETRY; NONHUMAN; OXYGENATION; PROTON NUCLEAR MAGNETIC RESONANCE; STREPTOMYCES; STREPTOMYCES OLIVACEUS;

ANTHRAQUINONES; ANTI-BACTERIAL AGENTS; CATALYSIS; GLYCOSYLTRANSFERASES; MOLECULAR STRUCTURE; PLASMIDS; STREPTOMYCES; SUBSTRATE SPECIFICITY;

BACTERIA (MICROORGANISMS); STREPTOMYCES; STREPTOMYCES OLIVACEUS;

EID: 0036854694     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np020112z     Document Type: Article

References (26)

1. Hallis, T. M.; Liu, H. W. Acc. Chem. Res. 1999, 32, 579-588.
2. Liu, H. W.; Thorson, J. S. Annu. Rev. Microbiol. 1994, 48, 223-256.
3. Trefzer, A.; Salas, J. A.; Bechthold, A. Nat. Prod. Rep. 1999, 16, 283-299.
4. Kirschning, A.; Bechthold, A.; Rohr, J. Top. Curr. Chem. 1997, 188, 1-84.
5. Künzel, E.; Faust, B.; Oelkers, C.; Weissbach, U.; Bearden, D. W.; Weitnauer, G.; Westrich, L.; Bechthold, A.; Rohr, J. J. Am. Chem. Soc. 1999, 121, 11058-11062.
6. Zhao, L. S.; Ahlert, J.; Xue, Y. Q.; Thorson, J. S.; Sherman, D. H.; Liu, H. W. J. Am. Chem. Soc. 1999, 121, 9881-9882.
7. Blanco, G.; Patallo, E. P.; Brana, A. F.; Trefzer, A.; Bechthold, A.; Rohr, J.; Mendez, C.; Salas, J. A. Chem. Biol. 2001, 8, 253-263.
8. Drautz, H.; Reuschenbach, P.; Zähner, H.; Rohr, J.; Zeeck, A. J. Antibiot. 1985, 38, 1291-1301.
9. Rodriguez, L.; Oelkers, C.; Aguirrezabalaga, I.; Brana, A. F.; Rohr, J.; Mendez, C.; Salas, J. A. J. Mol. Microbiol. Biotechnol. 2000,.2, 271-276.
10. Decker, H.; Rohr, J.; Motamedi, H.; Zahner, H.; Hutchinson, C. R. Gene 1995, 166, 121-126.
11. Weber, W.; Zähner, H.; Siebers, J.; Schröder, K.; Zeeck, A. Arch. Microbiol. 1979, 121, 111-116.
12. Egert, E.; Noltemeyer, M:; Siebers, J.; Rohr, J.; Zeeck, A. J. Antibiot. 1992, 45, 1190-1192.
13. Patallo, E. P.; Blanco, G.; Fischer, C.; Braña, A. F.; Rohr, J.; Mendez, C.; Salas, J. A. J. Biol. Chem. 2001, 276, 18765-18774.
14. Wohlert, S. E.; Blanco, G.; Lombo, F.; Fernandez, E.; Braña, A. F.; Reich, S.; Udvarnoki, G.; Mendez, C.; Decker, H.; Frevert, J.; Salas, J. A.; Rohr, J. J. Am. Chem. Soc. 1998, 120, 10596-10601.
15. Decker, H.; Haag, S.; Udvarnoki, G.; Rohr, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1107-1110.
16. Rodriguez, L.; Aguirrezabalaga, I.; Allende, N.; Braña, A. F.; Mendez, C.; Salas, J. A. Chem. Biol. 2002, 9, 721-729.
17. Rodriguez, L.; Rodriguez, D.; Olano, C.; Braña, A. F.; Mendez, C.; Salas, J. A. J. Bacteriol. 2001, 183, 5358-5363.
18. Aguirrezabalaga, I.; Olano, C.; Allende, N.; Rodriguez, L.; Braña, A. F.; Mendez, C.; Salas, J. A. Antimicrob. Agents Chemother. 2000, 44, 1266-1275.
19. The epimerization of the 3-position next to the 4-keto group is possible due to tautomerism (as shown in Figure 2, bold solid box).
20. Wohlert, S. E.; Lomovskaya, N.; Kulowski, K.; Fonstein, L.; Occi, J. L.; Gewain, K. M.; MacNeil, D. J.; Hutchinson, C. R. Chem. Biol. 2001, 8, 681-700.
21. Summers, R. G.; Donadio, S.; Staver, M. J.; Wendt-Pienkowski, E.; Hutchinson, C. R.; Katz, L. Microbiol. 1997, 143, 3251-3262.
22. Gaisser, S.; Böhm, G. A.; Doumith, M.; Raynal, M. C.; Dhillon, N.; Cortes, J.; Leadlay, P. F. Mol. Gen. Genet. 1998, 258, 78-88.
23. Chen, H. W.; Agnihotri, G.; Guo, Z. H.; Que, N. L. S.; Chen, X. M. H.; Liu, H. W. J. Am. Chem. Soc. 1999, 121, 8124-8125.
24. Chen, H. W.; Zhao, Z. B.; Hallis, T. M.; Guo, Z. H.; Liu, H. W. Angew. Chem., Int. Ed. 2001, 40, 607-610.
25. Fernandez, E.; Weissbach, U.; Reillo, C. S.; Braña, A. F.; Mendez, C.; Rohr, J.; Salas, J. A. J. Bacteriol. 1998, 180, 4929-4937.
26. Fernandez-Lozano, M. J.; Remsing, L. L.; Quiros, L. M.; Braña, A. F.; Fernandez, E.; Sanchez, C.; Mendez, C.; Rohr, J.; Salas, J. A. J. Biol. Chem. 2000, 275, 3065-3074.