SMB00708

Lysobactin

≥97% (HPLC)

• Synonym(s): 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
• Empirical Formula (Hill Notation): C₅₈H₉₇N₁₅O₁₇ · xC₂H₄O₂
• CAS Number: 118374-47-3
• Molecular Weight: 1276.48 (free base basis)
• UNSPSC Code: 41116107
• NACRES: NA.76

Properties

• Quality Level: 200
• Assay: ≥97% (HPLC)
• form: powder
• composition: counterion (acetate salt)
• solubility: DMSO: 1 mg/mL
• antibiotic activity spectrum: Gram-negative bacteria; Gram-positive bacteria
• Mode of action: cell wall synthesis | interferes
• storage temp.: −20°C
• 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
• 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

Description

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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable