Katanosins
From Wikipedia, the free encyclopedia
| Katanosins | |
|---|---|
 |
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| IUPAC name | N-[6-(2-amino-1-hydroxy-2-oxoethyl)-
15-butan-2-yl-18-[3-(diaminomethylideneamino)propyl]- 12-(1-hydroxyethyl)-3-(hydroxymethyl)-24-(1-hydroxy- 2-methylpropyl)-21-(2-methylpropyl)- 2,5,8,11,14,17,20,23,26-nonaoxo-28-phenyl-1-oxa- 4,7,10,13,16,19,22,25-octazacyclooctacos-27-yl]- 2-[(2-amino-4-methylpentanoyl)amino]-4-methylpentanamide |
| Other names | Lysobactin |
| Identifiers | |
| CAS number | [116340-02-4] |
| PubChem | |
| MeSH | |
| SMILES | OCC1NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)
C(CCCNC(=N)N)NC(=O)C(CC(C)C)NC(=O) C(NC(=O)C(NC(=O) C(CC(C)C)NC(=O)C(N)CC(C)C)C(OC1=O)c1ccccc1) C(O)C(C)C)C(C)CC )C(C)O)C(O)C(=O)N |
| Properties | |
| Molecular formula | C58H97N15O17 |
| Molar mass | 1276.51 |
| Appearance | solid |
| Density | - |
| Melting point |
- |
| Boiling point |
- |
| Solubility in water | - |
| Hazards | |
| Main hazards | Xn |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Katanosins are a group of antibiotics (also known as lysobactins). They are natural products with strong antibacterial potency.[1] So far, katanosin A and katanosin B (lysobactin) have been described.
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[edit] Sources
Katanosins have been isolated from the fermentation broth of microorganisms, such as Cytophaga[2] or the Gram-negative bacterium Lysobacter sp.[3].
[edit] Structure
Katanosins are cyclic depsipeptides (acylcyclodepsipeptides). These proteinogenic structures are not regular proteins from primary metabolism. They origin from the bacterial secondary metabolism. Accordingly, various non-proteinogenic (non-ribosomal) amino acids are found in katanosins, such as 3-hydroxyleucine, 3-hydroxyasparagine, allo-threonine and 3-hydroxyphenylalanine. All katanosins have a cyclic and a linear segment (“lariat structure”). The peptidic ring is closed with an ester bond (lactone). Katanosin A and B differ in the amino acid position 7. The minor metabolite Katanosin A has a valin in this position, whereas the main metabolite katanosin B carries an isoleucine.
[edit] Biological Activity
Katanosin antibiotics target the bacterial cell wall biosynthesis. They are highly potent against problematic Gram-positive hospital pathogens such as staphylococci and enterococci. Their promising biological activity attracted various biological and chemical research groups. Their in-vitro potency is comparable with the current “last defence” antibiotic vancomycin.
[edit] Chemical Synthesis
The first total syntheses of katanosin B (lysobactin) have been described in 2007.[4][5]
[edit] References
- ^ D. P. Bonner, J. O´Sullivan, S. K. Tanaka, J. M. Clark, R. R. Whitney, J. Antibiot. 1988, 41, 1745–1751 PMID 3209466
- ^ J. O´Sullivan, J. E. McCullough, A. A. Tymiak, D. R. Kirsch, W. H. Trejo, P. A. Prinicipe, J. Antibiot. 1988, 41, 1740–1744 PMID 3209465
- ^ J. I. Shoji, H. Hinoo, K. Matsumoto, T. Hattori, T. Yoshida, S. Matsuura, E. Kondo, J. Antibiot. 1988, 41, 713–718 PMID 3403364
- ^ F. von Nussbaum, S. Anlauf, J. Benet-Buchholz, D. Häbich, J. Köbberling, L. Musza, J. Telser, H. Rübsamen-Waigmann, N. A. Brunner Angew. Chem. 2007, 119, 2085–2088; Angew. Chem. Int. Ed. 2007, 46, 2039–2042 PMID 17211904
- ^ A. Guzman-Martinez, R. Lamer, M. S. VanNieuwenhze, J. Am. Chem. Soc. 2007, 129, 6017–6021 PMID 17432854
