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Key Documents

S3523

Sigma-Aldrich

Surfactin

from Bacillus subtilis, ≥98.0% (HPLC)

Synonyme(s) :

surfactin C

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About This Item

Formule empirique (notation de Hill):
C53H93N7O13
Numéro CAS:
Poids moléculaire :
1036.34
Code UNSPSC :
51102829
ID de substance PubChem :
Nomenclature NACRES :
NA.85

Source biologique

Bacillus subtilis

Niveau de qualité

Description

zwitterionic

Pureté

≥98.0% (HPLC)

Forme

powder

Conditions de stockage

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

Couleur

white to faint yellow

CMC

7.5-20 μmol/L (depending on methods)

Solubilité

ethanol: soluble 10 mg/mL

Spectre d'activité de l'antibiotique

Gram-negative bacteria
Gram-positive bacteria
fungi
mycoplasma
neoplastics
viruses

Mode d’action

cell membrane | interferes

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

NJGWOFRZMQRKHT-WGVNQGGSSA-N

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Description générale

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.

Actions biochimiques/physiologiques

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.

Autres remarques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)


Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

M M Nakano et al.
Journal of bacteriology, 170(12), 5662-5668 (1988-12-01)
Surfactin is a lipopeptide antibiotic produced by the cells of Bacillus subtilis ATCC 21332. A genetic locus responsible for surfactin production (sfp) was transferred from ATCC 21332 to JH642, a derivative of the standard B. subtilis 168. To study the
David J Gonzalez et al.
Microbiology (Reading, England), 157(Pt 9), 2485-2492 (2011-07-02)
Microbial competition exists in the general environment, such as soil or aquatic habitats, upon or within unicellular or multicellular eukaryotic life forms. The molecular actions that govern microbial competition, leading to niche establishment and microbial monopolization, remain undetermined. The emerging
Helen Y Fan et al.
Biochimica et biophysica acta, 1838(9), 2306-2312 (2014-03-19)
The effective charge of membrane-active molecules such as the fungicidal lipopeptide surfactin (SF) is a crucial property governing solubility, membrane partitioning, and membrane permeability. We present zeta potential measurements of liposomes to measure the effective charge as well as membrane
Sun Young Park et al.
Toxicology and applied pharmacology, 268(1), 68-78 (2013-01-31)
Surfactin, one of the most powerful biosurfactants, is a bacterial cyclic lipopeptide. Here, we investigated the anti-neuroinflammatory properties of surfactin in lipoteichoic acid (LTA)-stimulated BV-2 microglial cells. Surfactin significantly inhibited excessive production of the pro-inflammatory mediators TNF-α, IL-1β, IL-6, monocyte
F Alvarez et al.
Journal of applied microbiology, 112(1), 159-174 (2011-10-25)
This work was conducted to identify the antifungal compounds produced by two previously isolated Bacillus sp. strains: ARP(2) 3 and MEP(2) 18. Both strains were subjected to further analysis to determine their taxonomic position and to identify the compounds responsible

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