Longicatenamycins

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Longicatenamycin A (structural formula), a representative of the longicatenamycins

As Longicatenamycine refers to a group of antibiotics (also S-520 antibiotics called). These are natural substances with an antibacterial effect.

Occurrence

Longicatenamycins are obtained from the fermentation broth of microorganisms . This is how the biotechnological extraction from Streptomyces diastaticus was described.

structure

Longicatenamycins are cyclopeptides (cyclohexapeptides). The structure of the longicatenamycins was elucidated by means of Edman degradation reactions , amino acid analyzes and nuclear magnetic resonance spectroscopy . The longicatenamycins 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 longicatenamycins contain the non-ribosomal amino acids 3-hydroxy glutamic acid , 5-chloro tryptophan and various homoleucins .

Longicatenamycins differ at amino acid positions 4 (homoleucine), 5 ( D -valine or D -isoleucine) and 6 ( D- ornithine or D- lysine). Longicatenamycin A is apparently the main metabolite of the longicatenamycin complex.

Biological effect

The longicatenamycins are effective against gram-positive hospital germs such as B. against staphylococci and enterococci . The in vitro activity level of the natural longicatenamycins is worse than that of vancomycin .

Chemical synthesis

In 2008 the first synthesis of longicatenamycin A was described.

Individual evidence

  1. ↑ J. Shoji, R. Sakazaki, J Antibiot . 1970 , 23 , 418-419.
  2. ↑ J. Shoji, R. Sakazaki, J. Antibiot. 1970 , 23 , 432-436.
  3. ↑ J. Shoji, R. Sakazaki, J. Antibiot. 1970 , 23 , 519-521.
  4. ↑ T. Shiba, Y. Mukunoki, J. Antibiot. 1975 , 28 , 561-566, PMID 1158781 .
  5. ↑ T. Shiba, Y. Mukunoki, H. Akiyama, Tetrahedron Lett. 1974 , 35 , 3085-3086.
  6. ↑ F. von Nussbaum, S. Anlauf, C. Freiberg, J. Benet-Buchholz, J. Schamberger, T. Henkel, G. Schiffer, D. Häbich, ChemMedChem 2008 , 3 , 619-626, PMID 18246567 .