3-Amino-5-hydroxybenzoic acid in antibiotic biosynthesis. XI. Biological origins and semisynthesis of thionaphthomycins, and the structures of naphthomycins I and J

Journal of Antibiotics

Volumn 51, Issue 9, 1998, Pages 845-851

  Hooper, Antony M ^a   Rickards, Rodney W ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLCYSTEINE; ACETYLCYSTEINE DERIVATIVE; ANSAMYCIN DERIVATIVE; ANTIBIOTIC AGENT; HYDROXYBENZOIC ACID DERIVATIVE; NAPHTHOMYCIN A; NAPHTHOMYCIN F; NAPHTHOMYCIN H; NAPHTHOMYCIN I; NAPHTHOMYCIN J; THIONAPHTHOMYCIN DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBIOTIC BIOSYNTHESIS; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CULTURE MEDIUM; DRUG STRUCTURE; FERMENTATION; NONHUMAN; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STREPTOMYCES;

STREPTOMYCES;

EID: 0031705763     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.7164/antibiotics.51.845     Document Type: Article

References (22)

1. BRUFANI, M.: The ansamycins. Top. Antibiot. Chem. 1: 91-212, 1977
2. WEHRLI, W.: Ansamycins. Chemistry, biosynthesis and biological activity. Top. Curr. Chem. 72: 21-49, 1977
3. RINEHART, K. L., Jr. & L. S. SHIELD: Chemistry of the ansamycin antibiotics. Fortschr. Chem. Org. Naturst. 33: 231-307, 1976
4. RICKARDS, R. W.: Bio-organic chemistry of ansamycin and mitomycin antibiotics. In Studies in Natural Products Chemistry. Vol. 9. Structure and Chemistry (Part B). Ed., ATTA-UR-RAHMAN, pp. 431-445, Elsevier, Amsterdam, 1991
5. GHISALBA. O.: Biosynthesis of rifamycins (ansamycins) and microbial production of shikimate pathway precursors, intermediates and metabolites. Chimia 39: 79-88, 1985
6. 7N units in ansamycin antibiotics. J. Am. Chem. Soc. 118: 7486-7491, 1996
7. BECKER, A. M.; A. J. HERLT, G. L. HILTON, J. J. KIBBY & R. W. RICKARDS: 3-Amino-5-hydroxybenzoic acid in antibiotic biosynthesis. VI. Directed biosynthesis studies with ansamycin antibiotics. J. Antibiotics 36: 1323-1328, 1983
8. TRAXLER, P. & O. GHISALBA: A genetic approach to the biosynthesis of the rifamycin-chromophore in Nocardia mediterranei. V. Studies on the biogenetic origin of 3-substituents. J. Antibiotics 35: 1361-1366, 1982
9. HAMBLEY, T. W.; V. PARTHASARATHI, R. W. RICKARDS & G. B. ROBERTSON: Crystal structure and chirality of the ansamycin antibiotic actamycin. Aust. J. Chem. 44: 655-665, 1991
10. MEYER, M.; W. KELLER-SCHIERLEIN, S. MEGAHED, H. ZAHNER & A. SEGRE: Stoffwechselprodukte von Mikroorganismen. Schwefelhaltige Ansa-Verbindungen des Naphthomycin-Typus. Helv. Chim. Acta 69: 1356-1364, 1986
11. MUKHOPADHYAY, T.; C. M. M. FRANCO, G. C. S. REDDY, B. N. GANGULI & H. W. FEHLHABER: A new ansamycin antibiotic, naphthomycin H from a Streptomyces species Y-83,40369. J. Antibiotics 38: 948-951, 1985
12. WILLIAMS, T. H.: Naphthomycin, a novel ansa macrocyclic antimetabolite. Proton NMR spectra and structure elucidation using lanthanide shift reagent. J. Antibiotics 28: 85-86, 1975
13. KELLER-SCHIERLEIN, W.; M. MEYER, L. CELLAI, S. CERRINI, D. LAMBA, A. SEGRE, W. FEDELI & M. BRUFANI: Metabolites of microorganisms. 229. Absolute configuration of naphthomycin A determined by X-ray analysis and chemical degradation. J. Antibiotics 37: 1357-1361, 1984
14. FIESER, L. F. & R. H. BROWN: Synthesis of naphthoquinones for studies of the inhibition of enzyme systems. J. Am. Chem. Soc. 71: 3609-3614, 1949
15. TJEPKEMA, J. J.: The preparation of alkylthio substituted naphthoquinones-1,4 and benzoquinones-1,4. Rec. Trav. Chim. Pays-Bas 71: 853-856, 1952
16. Dictionary of Natural Products. Exec. Ed., J. BUCKINGHAM, Chapman and Hall, London, 1994. and references therein
17. HOTTA, M.; Y. HAYAKAWA, K. FURIHATA, A. SCHIMAZU, H. SETO & N. OTAKE: New ansamycin antibiotics, diastovaricins I and II. J. Antibiotics 39: 311-313, 1986
18. OKABE, T.; K. SUZUKI, H. SUZUKI, Y. INOUYE, S. NAKAMURA & N. TANAKA: Interaction of naphthomycin A with sulfhydryl comounds. J. Antibiotics 39: 316-317, 1986
19. CRICCHIO, R.; P. ANTONINI, G. C. LANCINI, G. TAMBORINI, R. J. WHITE & E. MARTINELLI: Thiazo rifamycins-I Structure and synthesis of rifamycins P, Q and verde, novel metabolites from mutants of Nocardia mediterranea. Tetrahedron 36: 1415-1421, 1980
20. CRICCHIO, R.: Thiazo rifamycins II Mechanism of the reaction between rifamycin S and 2-amino ethanethiol derivatives. Tetrahedron 36: 2009-2013, 1980
21. CRICCHIO, R.; P. ANTONINI & G. SARTORI: Thiazorifamycins. III. Biosynthesis of rifamycins P, Q and verde, novel metabolites from a mutant of Nocardia mediterranea. J. Antibiotics 33: 842-846, 1980
22. MCCAPRA, F. & Z. RAZAVI: Biosynthesis of luciferin in Pyrophorus pellucens. J. Chem. Soc., Chem. Commun. 153-154, 1976