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Merck
CN

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

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About This Item

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

Key Documents

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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 key

TXXDLVCKZNQGAV-QPXZYOHJSA-N

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-

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

Quality Level

200

Related Categories

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
028M4097V
14171210
14171209
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D P Bonner et al.
The Journal of antibiotics, 41(12), 1745-1751 (1988-12-01)
Lysobactin, an antibiotic isolated from a strain of Lysobacter, is 2 to 4-fold more active than vancomycin against aerobic and anaerobic Gram-positive bacteria. Included in the spectrum of lysobactin are Staphylococci, Streptococci, corynebacteria, clostridia and various other Gram-positive anaerobic bacteria.
Wonsik Lee et al.
Journal of the American Chemical Society, 138(1), 100-103 (2015-12-20)
Lysobactin, also known as katanosin B, is a potent antibiotic with in vivo efficacy against Staphylococcus aureus and Streptococcus pneumoniae. It was previously shown to inhibit peptidoglycan (PG) biosynthesis, but its molecular mechanism of action has not been established. Using

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