Katanosine

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Katanosine
Surname Katanosin A Katanosin B
Structural formula Katanosin A structure.png Lysobactin.png
other names Lysobactin
CAS number 116103-86-7 116340-02-4
PubChem 3082767 11693839
Molecular formula C 57 H 95 N 15 O 17 C 58 H 97 N 15 O 17
Molar mass 1262.48 g mol −1 1276.51 g mol −1
Physical state firmly
GHS
labeling
no classification available
H and P phrases see above
see above

As katanosin refers to a group of antibiotics (also Lysobactin -antibiotics called). These are natural substances with a strong antibacterial effect. Katanosin A and Katanosin B (lysobactin) have been described so far.

Occurrence

Katanosins are obtained from the fermentation medium of microorganisms . The biotechnological extraction from Cytophaga and from the Gram-negative bacterium Lysobacter sp. reported in Japan and the United States.

structure

Katanosins are depsipeptides . The katanosins are not regular peptides of the primary metabolism , rather they originate from the bacterial secondary metabolism , which also allows the incorporation of unusual, non-proteinogenic amino acids . The non-ribosomal amino acids 3-hydroxy leucine , 3-hydroxy phenylalanine , 3-hydroxy asparagine and allo- threonine are found in the katanosines .

All katanosins have a cyclic part and a linear tail. The ring is closed by an ester bond (these are cyclic depsipeptides , more precisely acylcyclodepsipeptides).

Katanosin A and B differ at the amino acid position 7. The secondary metabolite Katanosin A carries a valine , the main metabolite Katanosin B carries an isoleucine .

Biological effect

The katanosins disrupt the bacterial cell wall biosynthesis. They are highly potent against dreaded gram-positive hospital germs such as B. against staphylococci and enterococci . Because of their promising effects, biological and chemical research groups have studied the katanosin antibiotics. The in vitro level of activity of katanosins is comparable to that of vancomycin .

Chemical synthesis

In 2007 the first two syntheses of katanosin B (lysobactin) were described.

swell

  1. ^ DP Bonner, J. O´Sullivan, SK Tanaka, JM Clark, RR Whitney, J Antibiot . 1988 , 41 , 1745-1751 PMID 3209466
  2. ↑ J. O´Sullivan, JE McCullough, AA Tymiak, DR Kirsch, WH Trejo, PA Prinicipe, J. Antibiot. 1988 , 41 , 1740-1744 PMID 3209465
  3. ↑ JI Shoji, H. Hinoo, K. Matsumoto, T. Hattori, T. Yoshida, S. Matsuura, E. Kondo, J. Antibiot. 1988 , 41 , 713-718 PMID 3403364
  4. ↑ F. von Nussbaum, S. Anlauf, J. Benet-Buchholz, D. Häbich, J. Köbberling, L. Musza, J. Telser, H. Rübsamen-Waigmann, NA Brunner Angew. Chem. 2007 , 119 , 2085-2088; Angew. Chem. Int. Ed. 2007 , 46 , 2039-2042 PMID 17211904
  5. ↑ A. Guzman-Martinez, R. Lamer, MS VanNieuwenhze, J. Am. Chem. Soc. 2007 , 129 , 6017-6021 PMID 17432854