Absolute configurations of macrolide antibiotics of the bafilomycin and leucanicidin groups

Journal of Antibiotics

Volumn 50, Issue 12, 1997, Pages 1073-1077

  O'Shea, Michael G ^a   Rickards, Rodney W ^a   Rothschild, Jennifer M ^a   Lacey, Ernest ^b  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b MICROBIAL SCREENING TECHNOLOGIES PTY LTD   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

BAFILOMYCIN; BAFILOMYCIN A1; BAFILOMYCIN B1; BAFILOMYCIN C1; BAFILOMYCIN D; DRUG DERIVATIVE; L 681 110 B1; LEUCANICIDIN; MACROLIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0031471920     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.7164/antibiotics.50.1073     Document Type: Article

References (22)

1. Dictionary of Natural Products. Vol. 1. Exec. Ed., J. BUCKINGHAM, pp. 598-599, Chapman and Hall, London, 1994, and references therein
2. Dictionary of Natural Products. Vol. 3. Exec. Ed., J. BUCKINGHAM, p. 3627, Chapman and Hall, London, 1994, and references therein
3. LACEY, E.; J. H. GILL, M. L. POWER, R. W. RICKARDS, M. G. O'SHEA & J. M. ROTHSCHILD: Bafilolides, potent inhibitors of the motility and development of the free-living stages of parasitic nematodes. Int. J. Parasitol. 25: 349-357, 1995
4. 1 and D. FEMS Microbiol. Lett. 113: 155-159, 1993
5. COVER, T. L.; L. Y. REDDY & M. J. BLASER: Effects of ATPase inhibitors on the response of HeLa cells to Helicobacter pylori vacuolating toxin. Infect. Immun. 61: 1427-1431, 1993
6. 1 inhibits Helicobacter pylori-induced vacuolization of HeLa cells. Mol. Microbiol. 7: 323-327, 1993
7. 1 by X-ray crystallography and NMR techniques. Tetrahedron Lett. 28: 5565-5568, 1987
8. COREY, E. J. & J. W. PONDER: Stereochemistry of the hygrolidins. Tetrahedron Lett. 25: 4325-4328, 1984
9. 1. J. Chem. Soc., Chem. Commun. 1878-1880, 1987
10. 1. J. Chem. Soc., Perkin Trans. II 1073-1079, 1989
11. 1. J. Chem. Soc., Perkin Trans. II 717-724, 1990
12. WERNER, G.; H. HAGENMAIER, K. ALBERT & H. KOHLSHORN: The structure of the bafilomycins, a new group of macrolide antibiotics. Tetrahedron Lett. 47: 5193-5196, 1983
13. ISOGAI, A.; S. SAKUDA, S. MATSUMOTO, M. OGURA, K. FURIHATA, H. SETO & A. SUZUKI: The structure of leucanicidin, a novel insecticidal macrolide produced by Streptomyces halstedii. Agric. Biol. Chem. 48: 1379-1381, 1984
14. 1 und Leucanicidin. Helv. Chim. Acta 68: 83-94, 1985
15. WERNER, G.; H. HAGENMAIER, H. DRAUTZ, A. BAUMGARTNER & H. ZAHNER: Metabolic products of microorganisms. 224. Bafilomycins, a new group of macrolide antibiotics. Production, isolation, chemical structure and biological activity. J. Antibiotics 37: 110-117, 1984
16. BINDSEIL, K. U. & A. ZEECK: Chemistry of unusual macrolides. 1. Preparation of the aglycons of concanamycin A and elaiophylin. J. Org. Chem. 58: 5487-5492. 1993
17. SAKUDA, S.; A. ISOGAI, S. MATSUMOTO, M. OGURA, K. FURIHATA, H. SETO & A. SUZUKI: Isolation and structure of isobutyrylleucanicidin produced by Streptomyces halstedii. Agric. Biol. Chem. 51: 2841-2842, 1987
18. GORST-ALLMAN, C. P.; P. S. STEYN & C. J. RABIE: 7-epi-Brefeldin A, a co-metabolite of brefeldin A in Curvularia lunata. J. Chem. Soc., Perkin Trans. I 2387-2390, 1982
19. KRETSCHMER, A.; M. DORGERLOH, M. DEEG & H. HAGENMAIER: The structures of novel insecticidal macrolides: bafilomycins D and E, and oxohygrolidin. Agric. Biol. Chem. 49: 2509-2511, 1985
20. KINASHI, H.; K. SOMENO, K. SAKAGUCHI, T. HIGASHIJIMA & T. MIYAZAWA: Alkaline degradation products of concanamycin A. Tetrahedron Lett. 22: 3857-3860, 1981
21. KINASHI, H.; K. SAKAGUCHI, T. HIGASHIJIMA & T. MIYAZAWA: Structures of concanamycins B and C. J. Antibiotics 35: 1618-1620, 1982
22. HENSENS, O. D.; R. L. MONAGHAN, L. HUANG & G. ALBERS-SCHONBERG: Structure of the sodium and potassium ion activated adenosinetriphosphatase inhibitor L-681,110. J. Am. Chem. Soc. 105: 3672-3679, 1983