Katanosin

Katanosin B
Names
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
116340-02-4
ChemSpider 170823 YesY
Jmol interactive 3D Image
MeSH B Katanosin B
PubChem 197270
Properties
C58H97N15O17
Molar mass 1,276.50 g·mol−1
Appearance Solid
Density 1.42 g/cm3
Hazards
Main hazards Xn
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.

Sources

Katanosins have been isolated from the fermentation broth of microorganisms, such as Cytophaga.[2] or the Gram-negative bacterium Lysobacter sp.[3]

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 valine in this position, whereas the main metabolite katanosin B carries an isoleucine.

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.

Chemical synthesis

The first total syntheses of katanosin B (lysobactin) have been described in 2007.[4][5]

References

  1. Bonner, DP; O'Sullivan, J; Tanaka, SK; Clark, JM; Whitney, RR (1988). "Lysobactin, a novel antibacterial agent produced by Lysobacter sp. II. Biological properties". The Journal of antibiotics 41 (12): 1745–51. doi:10.7164/antibiotics.41.1745. PMID 3209466.
  2. O'Sullivan, J; McCullough, JE; Tymiak, AA; Kirsch, DR; Trejo, WH; Principe, PA (1988). "Lysobactin, a novel antibacterial agent produced by Lysobacter sp. I. Taxonomy, isolation and partial characterization". The Journal of antibiotics 41 (12): 1740–4. doi:10.7164/antibiotics.41.1740. PMID 3209465.
  3. Shoji, J; Hinoo, H; Matsumoto, K; Hattori, T; Yoshida, T; Matsuura, S; Kondo, E (1988). "Isolation and characterization of katanosins a and B". The Journal of antibiotics 41 (6): 713–8. doi:10.7164/antibiotics.41.713. PMID 3403364.
  4. Von Nussbaum, F; Anlauf, S; Benet-Buchholz, J; Häbich, D; Köbberling, J; Musza, L; Telser, J; Rübsamen-Waigmann, H; Brunner, NA (2007). "Structure and total synthesis of lysobactin (katanosin B)". Angewandte Chemie International Edition in English 46 (12): 2039–42. doi:10.1002/anie.200604232. PMID 17211904.
  5. Guzman-Martinez, A; Lamer, R; Vannieuwenhze, MS (2007). "Total synthesis of lysobactin". Journal of the American Chemical Society 129 (18): 6017–21. doi:10.1021/ja067648h. PMC 2151959. PMID 17432854.
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