Nosokomycins, new antibiotics discovered in an in vivo-mimic infection model using silkworm larvae. II: Structure elucidation

Journal of Antibiotics

Volumn 63, Issue 4, 2010, Pages 157-163

  Uchida, Ryuji ^a   Iwatsuki, Masato ^a   Kim, Yong Pil ^b   Ömura, Satoshi ^a   Tomoda, Hiroshi ^a  

^a KITASATO UNIVERSITY   (Japan)

^b IWAKI MEISEI UNIVERSITY   (Japan)

Author keywords

Anti methicillin resistant S. aureus antibiotics; Moenomycin family; Nosokomycins; Phosphoglycolipid; Structure elucidation

Indexed keywords

2,3 DIHYDROXYPROPIONIC ACID; BAMBERMYCIN; CYCLOPENTANONE DERIVATIVE; NOSOKOMYCIN A; NOSOKOMYCIN B; NOSOKOMYCIN C; NOSOKOMYCIN D; OLIGOSACCHARIDE; SESTERTERPENOID; TERPENOID; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG SOLUBILITY; DRUG STRUCTURE; IN VIVO STUDY; LARVA; LIQUID CHROMATOGRAPHY; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; NONHUMAN; PRIORITY JOURNAL; SILKWORM; STRUCTURE ANALYSIS;

ANIMALS; ANTI-BACTERIAL AGENTS; BOMBYX; CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; LARVA; MOLECULAR CONFORMATION; MOLECULAR SEQUENCE DATA; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OLIGOSACCHARIDES; PROPIONIC ACIDS; SESQUITERPENES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, ULTRAVIOLET; STREPTOMYCES;

BOMBYX MORI; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS AUREUS; STREPTOMYCES SP.;

EID: 77951715296     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2010.10     Document Type: Article

References (14)

1. Fukuda, T., Matsumoto, A., Takahashi, Y., Tomoda, H. & Ōmura, S. Phenatic acids A and B, new potentiators of antifungal miconazole activity produced by Streptomyces sp. K03-0132. J. Antibiot. 58, 252-259 (2005).
2. Koyama, N. et al. Stemphones, novel potentiator of imipenem activity against methicillin resitant Staphylococcus aureus, produced by Aspergillus sp. FKI-2136. J. Antibiot. 58, 695-703 (2005).
3. Iwatsuki, M. et al. Lariatins, novel anti-mycobacterial peptides with a lasso structure, produced by Rhodococcus jostii K01-B0171. J. Antibiot. 60, 357-363 (2007).
4. Uchida, R. et al. Nosokomycins, new antibiotics discovered in an in vivo-mimic infection model using silkworm larvae. I. Fermentation, isolation and biological properties. J. Antibiot. 63, 151-155 (2010).
5. Michael, K., Wolfgang, G. & Laszlo, V. Three-dimensional structure of moenomucon A, a potent inhibitor of penicillin-binding protein 1b. Eur. J. Biochem. 252, 500-507 (1998).
6. Marzan, S. et al. Moenomycin A: reactions at the lipid part. New structure-activity relations. Tetrahedron 50, 5299-5308 (1994).
7. Zehl, M., Pittenauer, E., Rizzi, A. & Allmaier, G. Characterization of moenomycin antibiotic complex by multistage MALD-IT/TOF-MS and ESI-IT-MS. J. Am. Soc. Mass Spectrum. 17, 1081-1090 (2006).
8. Arai, M. et al. Pholipomycin, a new member of phosphoglycolipid antibiotics II. physico-chemical properties and comparison with other members of this family of antibiotics. J. Antibiot. 12, 1055-1059 (1977).
9. Baizman, E. R. et al. Antibacterial activity of synthetic analogues based on the disaccharide structure of moenomycin, an inhibitor of bacterial transglycosylase. Microbiology 146, 3129-3140 (2000).
10. Ostash, B., Saghatelian, A. & Walker, S. A streamlined metabolic pathway for the biosynthesis of moenomycin A. Chem. Biol. 14, 257-267 (2007).
11. Ostash, B. et al. Complete characterization of the seventeen step moenomycin biosynthetic pathway. Biochemistry 48, 8830-8841 (2009).
12. Sakabe, C., Iwatsuki, M., Sakayanagi, M. & Hara, R. The abstract of 'Kikibunsekigijutsukenkyuukai'. P-13-A (2005).
13. Dominika, D. et al. Structure of the O-specific polysaccharide of Proteus penneri 103 containing ribitol and 2-aminoethanol phosphates. Carbohydrate Res. 337, 1535-1540 (2002).
14. Gary, E. M. & Chad, E. H. Long-range 1H-15N heteronuclear shift correlation at natural abundance. J. Nat. Prod. 63, 543-585 (2000).