Biosynthetic origin of hygromycin A

Antimicrobial Agents and Chemotherapy

Volumn 47, Issue 7, 2003, Pages 2065-2071

  Habib, El Sayed E ^a,c   Scarsdale, J Neel ^a   Reynolds, Kevin A ^a,b  

^a VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

^b Inst Struct Biol/Drug Discovery   (United States)

^c MANSOURA UNIVERSITY   (Egypt)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYBENZOIC ACID; 4 KETO 6 DEOXY DEXTRO MANNOSE; 6 DEOXY 5 KETO DEXTRO ARABINOHEXOFURANOSE; AMINE; AMINOCYCLITOL; ANTIBIOTIC A201A; ANTIBIOTIC AGENT; ARABINOSE DERIVATIVE; BACTERIAL ENZYME; BENZOIC ACID; CARBON 13; CHORISMIC ACID; FUCOSE; GLUCOSE; GLYCINE DERIVATIVE; GLYPHOSATE; HYDROXYL GROUP; HYGROMYCIN; INOSITOL; MANNOSE; NEOINOSAMINE 2; PEPTIDYLTRANSFERASE; PHENYLALANINE; POLYKETIDE SYNTHASE; PROPIONIC ACID; PUROMYCIN; TYROSINE; UNCLASSIFIED DRUG;

ARTICLE; DECARBOXYLATION; DRUG BINDING; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; HYPOTHESIS; ISOTOPE LABELING; MULTIDRUG RESISTANCE; MUTATION; OXIDATION; POLYMERIZATION; PRIORITY JOURNAL; PROTEIN TARGETING; RIBOSOME; STREPTOMYCES HYGROSCOPICUS; TRANSAMINATION;

ANTI-BACTERIAL AGENTS; CINNAMATES; ENZYME INHIBITORS; FERMENTATION; GLYCINE; HYGROMYCIN B; STREPTOMYCES;

EID: 0038677000     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.47.7.2065-2071.2003     Document Type: Article

References (35)

1. Ahlert, J., J. Distler, K. Mansouri, and W. Piepersberg. 1997. Identification of stsC, the gene encoding the L-glutamine:scyllo-inosose aminotransferase from streptomycin-producing Streptomycetes. Arch. Microbiol. 168:102-113.
2. Barker, J. L., and J. W. Frost. 2001. Microbial synthesis of p-hydroxybenzoic acid from glucose. Biotechnol. Bioeng. 76:376-390.
3. Brautaset, T., O. N. Sekurova, H. Sletta, T. E. Ellingsen, A. R. Strom, S. Valla, and S. B. Zotchev. 2000. Biosynthesis of the polyene antifungal antibiotic nystatin in Streptomyces noursei ATCC 11455: analysis of the gene cluster and deduction of the biosynthetic pathway. Chem. Biol. 7:395-403.
4. Brodersen, D. E., W. M. Clemons, Jr., A. P. Carter, R. J. Morgan-Warren, B. T. Wimberly, and V. Ramakrishnan. 2000. The structural basis for the action of the antibiotics tetracycline, pactamycin, and hygromycin B on the 30S ribosomal subunit. Cell 103:1143-1154.
5. Campelo, A. B., and J. A. Gil. 2002. The candicidin gene cluster from Streptomyces griseus IMRU 3570. Microbiology 148:51-59.
6. Ganoza, M. C., and M. C. Kiel. 2001. A ribosomal ATPase is a target for hygromycin B inhibition on Escherichia coli ribosomes. Antimicrob. Agents Chemother. 45:2813-2819.
7. Guerrero, M. D., and J. Modolell. 1980. Hygromycin A, a novel inhibitor of ribosomal peptidyltransferase. Eur. J. Biochem. 107:409-414.
8. Hansen, J. L., J. A. Ippolito, N. Ban, P. Nissen, P. B. Moore, and T. A. Steitz. 2002. The structures of four macrolide antibiotics bound to the large ribosomal subunit. Mol. Cell 10:117-128.
9. Hayashi, S. F., L. J. Norcia, S. B. Seibel, and A. M. Silvia. 1997. Structure-activity relationships of hygromycin A and its analogs: protein synthesis inhibition activity in a cell free system. J. Antibiot. (Tokyo) 50:514-521.
10. Hecker, S. J., M. L. Minich, and K. W. Werner. 1992. Semisynthetic modification of hygromycin A. 1. Synthesis and antibacterial activity of vinyl methyl and amide analogs. Bioorg. Med. Chem. Lett. 2:533-536.
11. Jarvinen, N., M. Maki, J. Rabina, C. Roos, P. Mattila, and R. Renkonen. 2001. Cloning and expression of Helicobacter pylori GDP-1-fucose synthesizing enzymes (GMD and GMER) in Saccharomyces cerevisiae. Eur. J. Biochem. 268:6458-6464.
12. Kiel, M. C., and M. C. Ganoza. 2001. Functional interactions of an Escherichia coli ribosomal ATPase. Eur. J. Biochem. 268:278-286.
13. Mann, R. L., and W. W. Bromer. 1958. The isolation of a second antibiotic from Streptomyces hygroscopicus. J. Am. Chem. Soc. 80:2714-2716.
14. Mann, R. L., R. M. Gale, and R. F. Van Abeele. 1953. Hygromycin. II. Isolation and properties. Antibiot. Chemother. 3:1279-1282.
15. Nakagawa, A., T. Fujimoto, S. Omura, J. C. Walsh, R. L. Stotish, and B. George. 1987. Hygromycin A, an antitreponemal substance. II. Therapeutic effect for swine dysentery. J. Antibiot. (Tokyo) 40:1627-1635.
16. Omura, S., A. Nakagawa, T. Fujimoto, K. Saito, K. Otoguro, and J. C. Walsh. 1987. Hygromycin A, an antitreponemal substance. I. Screening method and therapeutic effect for Treponema hyodysenteriae-caused infection in CF-1 mice. J. Antibiot. (Tokyo) 40:1619-1626.
17. Piel, J., C. Hertweck, P. R. Shipley, D. M. Hunt, M. S. Newman, and B. S. Moore. 2000. Cloning, sequencing and analysis of the enterocin biosynthesis gene cluster from the marine isolate Streptomyces maritimus: evidence for the derailment of an aromatic polyketide synthase. Chem. Biol. 7:943-955.
18. Piepersberg, W. 1997. Molecular biology, biochemistry and fermentation of aminoglycoside antibiotics, p. 81-164. In W. E. Strohl (ed.), Biotechnology of antibiotics. Marcel Dekker, New York, N.Y.
19. Pittenger, R. C., R. N. Wolfe, P. N. Hoehn, W. A. Daily, and J. M. McGuire. 1953. Hygromycin. I. Preliminary studies in the production and biologic activity on a new antibiotic. Antibiot. Chemother. 3:1268-1278.
20. Pojer, F., S. M. Li, and L. Heide. 2002. Molecular cloning and sequence analysis of the clorobiocin biosynthetic gene cluster: new insights into the biosynthesis of aminocoumarin antibiotics. Microbiology 148:3901-3911.
21. Poon, W. W., D. E. Davis, H. T. Ha, T. Jonassen, P. N. Rather, and C. F. Clarke. 2000. Identification of Escherichia coli ubiB, a gene required for the first monooxygenase step in ubiquinone biosynthesis. J. Bacteriol. 182:5139-5146.
22. Poulsen, S. M., C. Kofoed, and B. Vester. 2000. Inhibition of the ribosomal peptidyl transferase reaction by the mycarose moiety of the antibiotics carbomycin, spiramycin and tylosin. J. Mol. Biol. 304:471-481.
23. Sanders, D. A., A. G. Staines, S. A. McMahon, M. R. McNeil, C. Whitfield, and J. H. Naismith. 2001. UDP-galactopyranose mutase has a novel structure and mechanism. Nat. Struct. Biol. 8:858-863.
24. Saugar, I., E. Sanz, M. Rubio, A., J. C. Espinose, and A. Jimenez. 2002. Identification of a set of genes involved in the biosynthesis of the aminonucleoside moiety of antibiotic A201A from Streptomyces capreolus. Eur. J. Biochem. 269:5527-5535.
25. Schneider, S., M. E. Mohamed, and G. Fuchs. 1997. Anaerobic metabolism of L-phenylalanine via benzoyl CoA in the denitrifying bacterium Thauera aromatica. Arch. Microbiol. 168:310-320.
26. Somers, W. S., M. L. Stahl, and F. X. Sullivan. 1998. GDP-fucose synthetase from Escherichia coli: structure of a unique member of the short-chain dehydrogenase/reductase family that catalyzes two distinct reactions at the same active site. Structure 6:1601-1612.
27. Stalker, D. M., W. R. Hiatt, and L. Comai. 1985. A single amino acid substitution in the enzyme 5-enolpyruvylshikimate-3-phosphate synthase confers resistance to the herbicide glyphosate. J. Biol. Chem. 260:4724-4728.
28. Tercero, J. A., J. C. Espinosa, R. A. Lacalle, and A. Jimenez. 1996. The biosynthetic pathway of the aminonucleoside antibiotic puromycin, as deduced from the molecular analysis of the pur cluster of Streptomyces alboniger. J. Biol. Chem. 271:1579-1590.
29. Uyeda, M., M. Mizukami, K. Yokomizo, and K. Suzuki. 2001. Pentalenolactone I and hygromycin A, immunosuppressants produced by Streptomyces filipinensis and Streptomyces hygroscopicus. Biosci. Biotechnol. Biochem. 65:1252-1254.
30. 13C-labeled biofluids. J. Magn. Reson. 125:216-219.
31. Wu, B., Y. Zhang, and P. G. Wang. 2001. Identification and characterization of GDP-D-mannose 4,6-dehydratase and GDP-1-fucose synthetase in a GDP-1-fucose biosynthetic gene cluster from Helicobacter pylori. Biochem. Biophys. Res. Commun. 285:364-371.
32. Xiang, L., and B. S. Moore. 2002. Inactivation, complementation, and heterologous expression of encP, a novel bacterial phenylalanine ammonia-lyase gene. J. Biol. Chem. 277:32505-32509.
33. Yoshida, M., E. Takahashi, T. Uozumi, and T. Beppu. 1986. Hygromycin A and methoxyhygromycin A, novel inhibitors of K88 antigen synthesis of enterotoxic Escherichia coli strain. Agric. Biol. Chem. 50:143-149.
34. Zaretskaia, M. S. H., M. V. Nefelova, L. A. Barativa, and A. N. Polin. 1984. Composition of cell walls of 2 mutant strains of Streptomyces chrysomallus. Antibiotiki 29:902-906.
35. Zhang, Q., and H. Liu. 2001. Mechanistic investigation of UDP-galactopyranose mutase from Escherichia coli using 2- and 3-fluorinated UDP-galactofuranose as probes. J. Am. Chem. Soc. 123:6756-6766.