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Lysobactin

SIGMA/SMB00708 - ≥97% (HPLC)

Synonym: Katanosin B; L-Serine, D-leucyl-L-leucyl-(βR)-β-hydroxy-L-phenylalanyl-(3R)-3-hydroxy-L-leucyl-L-leucyl-D-arginyl-L-isoleucyl-L-allothreonylglycyl-(3S)-3-hydroxy-L-asparaginyl-, (11→3)-lactone

CAS Number: 118374-47-3 (free base)
Empirical Formula (Hill Notation): C58H97N15O17 · xC2H4O2
Molecular Weight: 1276.48 (free base basis)
Linear Formula: C58H97N15O17 · xC2H4O2
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-SMB00708-1MG 1 mg
 $153.00
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antibiotic activity spectrum Gram-negative bacteria
  Gram-positive bacteria
assay ≥97% (HPLC)
composition counterion (acetate salt)
form powder
InChI 1S/C58H97N15O17.C2H4O2/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-
InChI key TXXDLVCKZNQGAV-QPXZYOHJSA-N
mode of action cell wall synthesis | interferes
Quality Level 200 
SMILES string N1[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)OC([C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C1=O)[C@H](CC)C)CCCN=C(N)N)CC(C)C)[C@H](O)C(C)C)NC(=O)[C@@H](NC(=O)[C@H](N)CC(C)C)CC(C)C)c2ccccc2)CO)[C@H](O)C(=O)N)[C@@H](O)C.OC(=O)C
solubility DMSO: 1 mg/mL
storage temp. −20°C
Biochem/physiol Actions: Lysobactin is a cyclic peptide with strong antibacterial activity against many bacterial strains including Staphylococcus aureus, Salmonella typhosa, and Klebsiella aerogenes. Lysobactin is reported to have MIC values of 0.2, 25, and 25 μg/mL for the above listed bacteria respectively, which is significantly higher than the potency reported for vancomycin for the same bacteria (MIC values 0.8, >100, and >100 μg/mL respectively).

The mechanism of action of lysobactin is attributed to its interaction with lipid I and lipid II in the bacterial cell wall. Lysobactin forms a 1:1 complex with lipid I and lipid II causing interference in peptidoglycan synthesis which is essential for bacterial viability. Furthermore, lysobactin was not found to be hemolytic at concentrations above its MIC.
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity ≥97% (HPLC)
Storage Temp. −20°C
UNSPSC 41116107

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