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S3523

Sigma-Aldrich

Surfactin

from Bacillus subtilis, ≥98.0% (HPLC)

Synonyme(s) :

surfactin C

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10 MG
374,00 €
50 MG
1 510,00 €

About This Item

Formule empirique (notation de Hill) :
C53H93N7O13
Numéro CAS:
24730-31-2
Poids moléculaire :
1036.34
Code UNSPSC :
51102829
ID de substance PubChem :
24899562
Nomenclature NACRES :
NA.85

374,00 €

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Source biologique

Bacillus subtilis

Niveau de qualité

200

Description

zwitterionic

Essai

≥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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Catégories apparentées

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[1].

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[1].

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)

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Certificats d'analyse (COA)

Lot/Batch Number
0000422734
0000422734
0000411103
0000411103
0000369072

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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
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
Darlane Wellen Freitas de Oliveira et al.
Colloids and surfaces. B, Biointerfaces, 101, 34-43 (2012-07-17)
In this work a low cost medium for the production of a biosurfactant by Bacillus subtilis LAMI005 and the kinetics of surfactin production considering the effect of initial substrate concentration were investigated. First, cashew apple juice supplementation for optimal production
Guillaume Henry et al.
Cellular microbiology, 13(11), 1824-1837 (2011-08-16)
The lipopeptide surfactin secreted by plant-beneficial bacilli has crucial biological functions among which the ability to stimulate immune-related responses in host tissues. This phenomenon is important for biological control of plant diseases but its molecular basis is still poorly understood.
N Behary et al.
Colloids and surfaces. B, Biointerfaces, 90, 137-143 (2011-11-08)
This article deals with an alternative method for bio-separation of surfactin produced by Bacillus subtilis using sorption method on nonwoven PET (polyethylene terephthalate) fibrous membranes functionalized with chitosan. In the first part of the study, surface functionalization of the PET
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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