Katanosins

Chembox new
ImageFile= lysobactin.pngImageSize=
IUPACName=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
OtherNames=Lysobactin
Section1= Chembox Identifiers
CASNo=116340-02-4
PubChem=197270
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
MeSHName=Katanosin B
Section2= Chembox Properties
Formula=C₅₈H₉₇N₁₅O₁₇
MolarMass=1276.51
Appearance=solid
Density=-
MeltingPt=-
BoilingPt=-
Solubility=-
Section3= Chembox Hazards
MainHazards=Xn
FlashPt=
Autoignition=

Katanosins are a group of antibiotics (also known as lysobactins). They are natural products with strong antibacterial potency. [D. P. Bonner, J. O´Sullivan, S. K. Tanaka, J. M. Clark, R. R. Whitney, "J. Antibiot." 1988, "41", 1745–1751 PMID 3209466] So far, katanosin A and katanosin B (lysobactin) have been described.

ources

Katanosins have been isolated from the fermentation broth of microorganisms, such as "Cytophaga" [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] or the Gram-negative bacterium "Lysobacter sp." [J. I. Shoji, H. Hinoo, K. Matsumoto, T. Hattori, T. Yoshida, S. Matsuura, E. Kondo, "J. Antibiot." 1988, "41", 713–718 PMID 3403364] .

tructure

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.

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. [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]

References