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Merck
CN

S3523

Surfactin

from Bacillus subtilis, ≥98.0% (HPLC)

Synonym(s):

surfactin C

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About This Item

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

Key Documents

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InChI key

NJGWOFRZMQRKHT-WGVNQGGSSA-N

biological source

Bacillus subtilis

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

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

Quality Level

200

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Related Categories

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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

Lot/Batch Number
0000502656
0000502656
0000502657
0000502657
0000486896

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K Tsuge et al.
Antimicrobial agents and chemotherapy, 45(12), 3566-3573 (2001-11-16)
Surfactin is a cyclic lipopeptide biosurfactant. Transposon mutagenesis was performed in Bacillus subtilis strain 168, and a surfactin-susceptible mutant, strain 801, was isolated. Analysis of the region of insertion revealed that yerP was the determinant of surfactin self-resistance. YerP had
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
Emilia Ghelardi et al.
Applied and environmental microbiology, 78(18), 6540-6544 (2012-07-10)
Multicellular communities produced by Bacillus subtilis can adopt sliding or swarming to translocate over surfaces. While sliding is a flagellum-independent motility produced by the expansive forces in a growing colony, swarming requires flagellar functionality and is characterized by the appearance
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
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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