Nisin

Nisin
  • CAS No.:1414-45-5
Other grades of this product :
Nisin Basic information
Description References
Product Name:Nisin
Synonyms:L-Isoleucyl-(Z)-2,3-didehydro-2-aminobutanoyl-D-cysteinyl-L-isoleucyl-2,3-didehydroalanyl-L-leucyl-L-cysteinyl-threo-3-mercapto-D-2-aminobutanoyl-L-prolylglycyl-L-cysteinyl-L-lysyl-threo-3-mercapto-D-2-aminobutanoylglycyl-L-alanyl-L-leucyl-L-methionylglycyl-L-cysteinyl-L-asparaginyl-L-methionyl-L-lysyl-threo-3-mercapto-D-2-aminobutanoyl-L-alanyl-threo-3-mercapto-D-2-aminobutanoyl-L-cysteinyl-L-histidyl-L-cysteinyl-L-seryl-L-isoleucyl-L-histidyl-L-valyl-2,3-didehydroalanyl-L-lysine cyclic (3->7),(8->11),(13->19),(23->26),(25->28)-pentakis(sulfide);NISIN;nsc-112903;Streptococcus element (element);Nisin from Lactococcus lactis Vetec(TM) reagent grade, 2.5% (balance sodium chloride and denatured milk solids);Nisin from Lactococcus lactis;NISINSTREPTOCOCCUS LACTIS;nisin from streptococcus lactis
CAS:1414-45-5
MF:C143H230N42O37S7
MW:3354.07
EINECS:215-807-5
Product Categories:Food & Feed ADDITIVES;Food additive;Flavors and fragrances;PeptidesAntibiotics;Preservatives and Disinfectants;Antibacterial;Antibiotics;Antibiotics A to;Antibiotics by Application;Antibiotics N-SAntibiotics;Chemical Structure Class;Interferes with Cell Membrane Permeability (Ionophores)Spectrum of Activity;L - ZAntibiotics;Mechanism of Action;1414-45-5
Mol File:1414-45-5.mol
Nisin Chemical Properties
Boiling point 2967℃
density 1.02 g/mL
Fp >110°(230°F)
storage temp. -20°C
solubility insoluble in H2O; insoluble in EtOH; ≥5.63 mg/mL in DMSO with gentle warming and ultrasonic
form solution
Water Solubility Soluble in water
Merck 13,6592
CAS DataBase Reference1414-45-5
Safety Information
Hazard Codes Xn
Risk Statements 22-36/37/38
Safety Statements 22-24/25-36-26
WGK Germany 3
RTECS QU3340000
10
MSDS Information
ProviderLanguage
Nisin English
SigmaAldrich English
Nisin Usage And Synthesis
DescriptionAs a ribosomally synthesized peptide, Nisin has broad-spectrum antibacterial activity that is produced by the Lactococcus lactis. In the food industry, Nisin is obtained from the cultivating of Lactococcus lactis on natural substrates, such as milk or dextrose. It serves as a natural, antibacterial, and toxicologically safe food preservative which is protect against many bacteria that are food-spoilage pathogens. As a food additive, Nisin is popularly used in food production, such as milk, meats, fast food, beverages, health care products and medicines, etc. It is effective to decrease sterilization time, lower temperature during food sterilization, improve food quality, lessen damage to nutrition, and extend shelf life by suppressing Gram-positive spoilage and pathogenic bacteria. Besides, it has been studied as a possible treatment for infections of Clostridium difficile combined with miconazole. It was originally isolated in the late 1930s and approved as an additive for food use in the USA in the late 1960s. Nisin functions by binding to cell wall precursor lipid components of bacteria and disrupts cell wall production. Once introduced Nisin initially blends with Lipid II, a precursor molecule used to form bacterial cell wall, to create a complex. The complex penetrates the cell wall and breaks into the cytoplasmic membrane and form pores, through which the internal cytoplasmic content oozes out leading to bacterial inhibition or death.
Referenceshttps://en.wikipedia.org/wiki/Nisin http://www.innovateus.net/food/natural-preservative-nisin http://www.sigmaaldrich.com/catalog/product/sigma/n5764?lang=en&region=US&gclid=CPu1xf6aq9MCFcSOfgodvmcHZA
Chemical PropertiesCrystals from ethanol. Derived from Streptococcus lactis Lancefield Group N.
UsesNisin is an antimicrobial agent derived from pure culture fermenta- tions of certain strains of streptococcus lactis lancefield group n. nisin preparation contains nisin, a group of related peptides with antibiotic activity. it is used to inhibit the outgrowth of clostridium botulinum spores and toxin formation in pasteurized cheese spreads and pasteurized process cheese spreads; pasteurized cheese spread with fruits, vegetables, or meats; and pasteurized process cheese spread with fruits, vegetables, or meats.
UsesNisin is a particularly effective bacteriosin against C. botulinum, is allowed in processed cheese food.
UsesAn antibiotic with bactericidal action
DefinitionChEBI: A type-A lantibiotic containing 34 amino acid residues (including lanthionine (Lan), methyllanthionine (MeLan), didehydroalanine (Dha) and didehydroaminobutyric acid (Dhb)) and five thioether bridges. It is obtained by fermentation of the bacterium L ctococcus lactis and shows particular activity against Clostridium botulinum. It is used in the production of various processed foods to suppress Gram-positive spoilage and pathogenic bacteria and so extend shelf life.
Biological Activitynisin is an antibacterial peptide.nisin is produced by the lactic acid bacterium l. lactis using uncommon amino acids, including lanthionine, and is a member of the class of antibiotics referred to as lantibiotics.
Biochem/physiol ActionsNisin (Nisaplin) is produced by Lactococcus lactis. It is an effective lantibiotic peptide bactericidal agent. Nisin is a broad spectrum antimicrobial bacteriocin which affects Gram-positive bacteria, however, it has little or no effect on Gram-negative bacteria, yeasts or fungi.It was demonstrated that nisin has capability to inhibit the growth of almost all tested Gram-positive beer-spoilage bacteria. Of 122 Gram-positive bacteria strains (predominantly Lactobacilli and Pediococci), 93% were sensitive to 100 units of nisin. In contrast, out of the 32 Gram-negative strains tested, only the genus Flavobacter proved to be affected by nisin.Nisin exerts its antimicrobial activity by binding to lipid II which is a membrane-bound advanced intermediate involved in the biosynthesis of bacterial cell wall. By doing so, nisin sequesters lipid II from its functional location. In addition, the nisin-lipid II complex leads to formation of pores in the membrane causing cell death.
in vitroprevious study showed that the sperm motility could be completely inhibited with nisin the minimum effective concentration of nisin required to immobilize sperm in vitro within 20 s was found to be 50 μg in rat, 200 μg in rabbit and 300-400 μg in monkey and human. such inhibitory effect on sperm motility was found to be dose- and time-dependent [1].
in vivointravaginal administration of nisin before mating during proestrus-estrous transition phase caused complete arrest of sperm motility and blockage of conception. subacute toxicity studies in rats showed that, repetitive intravaginal application of nisin at the dose of 200 microg for 14 days caused no abnormalities either in the length of estrous cycle or in the morphology of vaginal epithelial cells. moreover, no histopathological abnormalities in vaginal tissue or any change in blood and serum biochemical profiles were seen. in addition, no adverse effects were found on subsequent reproductive performance, development of pups and neonate survival [1].
Purification MethodsThis polypeptide from S. lactis is purified by crystallisation from 80% (v/v) EtOH and by countercurrent distribution. The synthetic polypeptide antibiotic can also be purified by preparative HPLC and assayed by HPLC on a Nucleosil 3007C18 (6 x 250mm) column using a MeCN—0.01M HCl gradient (30-50%), at 2%/minute, and flow rate of 1.5mL/minute to give a retention time of 8.1 minutes; or MeCN—0.3M guanidine-HCl gradient (30-50%), at 2%/minute, and flow rate of 1.5ml/minute to give a retention time of 10.9minutes. FAB-MS gave the pseudomolecular ion m/z at 3352.7 (M + H)+. It is soluble in dilute acid and is stable even on boiling. [Berridge et al. Biochem J 52 529 1952, synthesis by Fukase et al. Tetrahedron Lett 29 795 1988.]
references[1] aranha c, gupta s, reddy kv. contraceptive efficacy of antimicrobial peptide nisin: in vitro and in vivo studies. contraception. 2004 apr;69(4):333-8.

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