S3523

Surfactin

from Bacillus subtilis, ≥98.0% (HPLC)

• Synonym(s): surfactin C
• Empirical Formula (Hill Notation): C₅₃H₉₃N₇O₁₃
• CAS Number: 24730-31-2
• Molecular Weight: 1036.34
• UNSPSC Code: 51102829
• PubChem Substance ID: 24899562
• NACRES: NA.85

Properties

• biological source: Bacillus subtilis
• Quality Level: 200
• description: zwitterionic
• assay: ≥98.0% (HPLC)
• form: powder
• storage condition: (Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.)
• color: white to faint yellow
• CMC: 7.5-20 μmol/L (depending on methods)
• solubility: ethanol: soluble 10 mg/mL
• antibiotic activity spectrum: Gram-negative bacteria; Gram-positive bacteria; fungi; mycoplasma; neoplastics; viruses
• mode of action: cell membrane | interferes
• storage temp.: 2-8°C
• SMILES string: CC(C)CCCCCCCCC[C@@H]1CC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)O1
• InChI: 1S/C53H93N7O13/c1-30(2)20-18-16-14-13-15-17-19-21-36-28-43(61)54-37(22-23-44(62)63)47(66)55-38(24-31(3)4)48(67)57-40(26-33(7)8)51(70)60-46(35(11)12)52(71)58-41(29-45(64)65)50(69)56-39(25-32(5)6)49(68)59-42(27-34(9)10)53(72)73-36/h30-42,46H,13-29H2,1-12H3,(H,54,61)(H,55,66)(H,56,69)(H,57,67)(H,58,71)(H,59,68)(H,60,70)(H,62,63)(H,64,65)/t36-,37+,38+,39-,40-,41+,42+,46+/m1/s1
• InChI key: NJGWOFRZMQRKHT-WGVNQGGSSA-N

Description

General description

Chemical structure: peptide

Application

Surfactin is used as a surfactant to mediate flux of mono-and divalent cations, such as calcium, across lipid bilayer membranes. It is also used to study antitumor activity, activity against enveloped viruses, activity against the protoplast of Bacillus megaterium and the activity against Mycoplasma.

Biochem/physiol Actions

Surfactin is a lipopeptide antibiotic that is composed of one β-hydroxy fatty acid, which has a long fatty acid moiety, and seven amino acids. Three of them have D configurations. It is a powerful biosurfactant that causes lysis of erythrocytes and bacteria. It is also a clotting inhibitor. Surfactin is thought to disrupt or disintegrate membranes via physicochemical interaction with the membranes.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)