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Katanosin

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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
3D model (JSmol)
ChemSpider
MeSH B Katanosin B
  • InChI=1S/C58H97N15O17/c1-12-30(10)39-53(85)71-40(31(11)75)52(84)64-24-38(76)69-42(45(78)47(60)79)55(87)68-37(25-74)57(89)90-46(32-17-14-13-15-18-32)43(73-51(83)36(23-28(6)7)66-48(80)33(59)21-26(2)3)56(88)72-41(44(77)29(8)9)54(86)67-35(22-27(4)5)50(82)65-34(49(81)70-39)19-16-20-63-58(61)62/h13-15,17-18,26-31,33-37,39-46,74-75,77-78H,12,16,19-25,59H2,1-11H3,(H2,60,79)(H,64,84)(H,65,82)(H,66,80)(H,67,86)(H,68,87)(H,69,76)(H,70,81)(H,71,85)(H,72,88)(H,73,83)(H4,61,62,63) checkY
    Key: KQMKBWMQSNKASI-UHFFFAOYSA-N checkY
  • InChI=1/C58H97N15O17/c1-12-30(10)39-53(85)71-40(31(11)75)52(84)64-24-38(76)69-42(45(78)47(60)79)55(87)68-37(25-74)57(89)90-46(32-17-14-13-15-18-32)43(73-51(83)36(23-28(6)7)66-48(80)33(59)21-26(2)3)56(88)72-41(44(77)29(8)9)54(86)67-35(22-27(4)5)50(82)65-34(49(81)70-39)19-16-20-63-58(61)62/h13-15,17-18,26-31,33-37,39-46,74-75,77-78H,12,16,19-25,59H2,1-11H3,(H2,60,79)(H,64,84)(H,65,82)(H,66,80)(H,67,86)(H,68,87)(H,69,76)(H,70,81)(H,71,85)(H,72,88)(H,73,83)(H4,61,62,63)
    Key: KQMKBWMQSNKASI-UHFFFAOYAZ
  • O=C(N)C(O)C2C(=O)NC(C(=O)OC(c1ccccc1)C(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)N2)C(O)C)C(C)CC)CCCN=C(N)N)CC(C)C)C(O)C(C)C)NC(=O)C(NC(=O)C(N)CC(C)C)CC(C)C)CO
Properties
C58H97N15O17
Molar mass 1276.502 g·mol−1
Appearance Solid
Density 1.42 g/cm3
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Xn
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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 non-proteinogenic structures are not ordinary proteins derived from primary metabolism. Rather, they originate from bacterial secondary metabolism. Accordingly, various non-proteinogenic (non-ribosomal) amino acids are found in katanosins, such as 3-hydroxyleucine, 3-hydroxyasparagine, allothreonine and 3-hydroxyphenylalanine. All katanosins have a cyclic and a linear segment (“lariat structure”). The peptidic ring is closed with an ester bond (lactone).[citation needed]

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.[citation needed]

Biological activity

Katanosin antibiotics target the bacterial cell wall biosynthesis.[4] 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.[citation needed]

Chemical synthesis

The first total syntheses of katanosin B (lysobactin) have been described in 2007.[5][6]

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. ^ Lee, Wonsik; Schaefer, Kaitlin; Qiao, Yuan; Srisuknimit, Veerasak; Steinmetz, Heinrich; Müller, Rolf; Kahne, Daniel; Walker, Suzanne (2016). "The Mechanism of Action of Lysobactin". Journal of the American Chemical Society. 138 (1): 100–103. doi:10.1021/jacs.5b11807. PMC 4817722. PMID 26683668.
  5. ^ 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.
  6. ^ 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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