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N5764

Sigma-Aldrich

Nisin from Lactococcus lactis

potency: ≥900 IU/mg

Synonym(s):

Nisin A

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About This Item

Empirical Formula (Hill Notation):
C143H230N42O37S7
CAS Number:
1414-45-5
Molecular Weight:
3354.07
MDL number:
MFCD00131724
UNSPSC Code:
51102829
PubChem Substance ID:
24897751
NACRES:
NA.85
Pricing and availability is not currently available.

form

powder

Quality Level

200

potency

≥900 IU/mg

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

cell membrane | interferes

storage temp.

2-8°C

SMILES string

[H]N[C@@H]([C@@H](C)CC)C(=O)N\C(=C\C)C(=O)N[C@H]1CSC[C@H](NC(=O)[C@H](CC(C)C)NC(=O)C(=C)NC(=O)[C@@H](NC1=O)[C@@H](C)CC)C(=O)N[C@H]2[C@H](C)SC[C@H](NC(=O)CNC(=O)[C@@H]3CCCN3C2=O)C(=O)N[C@H](CCCCN)C(=O)N[C@@H]4[C@@H](C)SC[C@H](NC(=O)CNC(=O)[C@H](CCSC)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)CNC4=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCCN)C(=O)N[C@H]5[C@H](C)SC[C@@H]6NC(=O)[C@@H](NC(=O)[C@H](C)NC5=O)[C@H](C)SC[C@H](NC(=O)[C@H](Cc7cnc[nH]7)NC6=O)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](Cc8cnc[nH]8)C(=O)N[C@@H](C(C)C)C(=O)NC(=C)C(=O)N[C@@H](CCCCN)C(O)=O

InChI

1S/C143H230N42O37S7/c1-24-69(11)105(148)135(213)162-82(27-4)118(196)174-94-58-225-59-95(175-123(201)89(48-67(7)8)169-115(193)74(16)158-138(216)107(70(12)25-2)180-132(94)210)133(211)184-112-79(21)229-61-96(160-104(190)56-152-134(212)100-38-34-44-185(100)142(112)220)128(206)164-84(36-29-32-42-145)120(198)182-109-76(18)226-60-97(161-103(189)55-151-117(195)85(39-45-223-22)165-122(200)88(47-66(5)6)168-113(191)72(14)156-102(188)54-153-136(109)214)129(207)171-92(51-101(147)187)125(203)166-86(40-46-224-23)119(197)163-83(35-28-31-41-144)121(199)183-110-77(19)228-63-99-130(208)170-90(49-80-52-149-64-154-80)124(202)176-98(62-227-78(20)111(141(219)177-99)181-116(194)75(17)159-140(110)218)131(209)173-93(57-186)127(205)179-108(71(13)26-3)139(217)172-91(50-81-53-150-65-155-81)126(204)178-106(68(9)10)137(215)157-73(15)114(192)167-87(143(221)222)37-30-33-43-146/h27,52-53,64-72,75-79,83-100,105-112,186H,15-16,24-26,28-51,54-63,144-146,148H2,1-14,17-23H3,(H2,147,187)(H,149,154)(H,150,155)(H,151,195)(H,152,212)(H,153,214)(H,156,188)(H,157,215)(H,158,216)(H,159,218)(H,160,190)(H,161,189)(H,162,213)(H,163,197)(H,164,206)(H,165,200)(H,166,203)(H,167,192)(H,168,191)(H,169,193)(H,170,208)(H,171,207)(H,172,217)(H,173,209)(H,174,196)(H,175,201)(H,176,202)(H,177,219)(H,178,204)(H,179,205)(H,180,210)(H,181,194)(H,182,198)(H,183,199)(H,184,211)(H,221,222)/b82-27+/t69-,70-,71-,72-,75-,76?,77?,78?,79?,83-,84+,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,105-,106-,107-,108-,109+,110-,111-,112-/m0/s1

InChI key

NVNLLIYOARQCIX-ILAIHEEGSA-N

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General description

Chemical structure: peptide

Application

Nisin is a polycyclic lantibiotic produced by Lactococcus lactis. It is commonly used as a food preservative. It is also used as a selective agent in cell culture for the isolation of gram-negative bacteria, yeast, and molds. Nisin has been used in bioassays to study posttranslational modification[1].
Used to form targeted pores in cell membranes that are mediated by lipid II. Used to study the assembly and stability of nisin-lipid II pore complexes.

Biochem/physiol Actions

Nisin binds to cell wall precursor lipid components of bacteria and disrupts cell wall production. Nisin alters the cell membrane which results in the leakage of cytoplasmic components and destruction of the proton motive force[1].
Nisin is an antibiotic with bactericidal action. It binds to the lipid A portion of bacterial lipopolysaccharides and induces pore formation in the membranes of cortex cells from excised sorghum roots.

Mode of Action: Binds to and interferes with the permeability of the cytoplasmic membrane.
Antimicrobial spectrum: Gram-negative and Gram-positive bacteria (requires chelator such as EDTA).

Packaging

Package size based on weight of total solids

Other Notes

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000399844
0000377951
0000360816
0000360816
0000377951

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Olli Koponen et al.
Microbiology (Reading, England), 148(Pt 11), 3561-3568 (2002-11-13)
Nisin produced by Lactococcus lactis subsp. lactis is a 34-residue antibacterial polypeptide and belongs to a group of post-translationally modified peptides, lantibiotics, with dehydrated residues and cyclic amino acids, lanthionines. These modifications are supposed to be made by enzymes encoded
Qi Zhang et al.
Proceedings of the National Academy of Sciences of the United States of America, 109(45), 18361-18366 (2012-10-17)
Lanthionine-containing peptides (lanthipeptides) are a family of ribosomally synthesized and posttranslationally modified peptides containing (methyl)lanthionine residues. Here we present a phylogenomic study of the four currently known classes of lanthipeptide synthetases (LanB and LanC for class I, LanM for class
Paul D Cotter
Bioengineered, 3(6), 313-319 (2012-08-28)
While the bacteriocin Nisin has been employed by the food industry for 60 y, it remains the only bacteriocin to be extensively employed as a food preservative. This is despite the fact that the activity of Nisin against several food
Michaela Wenzel et al.
Antimicrobial agents and chemotherapy, 56(11), 5749-5757 (2012-08-29)
Mersacidin, gallidermin, and nisin are lantibiotics, antimicrobial peptides containing lanthionine. They show potent antibacterial activity. All three interfere with cell wall biosynthesis by binding lipid II, but they display different levels of interaction with the cytoplasmic membrane. On one end
Des Field et al.
PloS one, 7(10), e46884-e46884 (2012-10-12)
Nisin is a bacteriocin widely utilized in more than 50 countries as a safe and natural antibacterial food preservative. It is the most extensively studied bacteriocin, having undergone decades of bioengineering with a view to improving function and physicochemical properties.
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Questions

1–4 of 4 Questions  

  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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  3. Bonjour, Avec quoi peut on re-suspendre ce produit? Peut on le stocker après re-suspension? Merci par avance

    1 answer

    1. The solubility has not been tested. However, several literature sources indicate that this material is soluble in dilute acids. Solubility was quite high at low pH (57 mg/ml at pH 2) and much lower at high pH (0.25 mg/ml at pH 8 to 12). Dissolving the compound in water is not recommended. In addition, the product may also be soluble in DMSO with gentle warming and ultrasonication, up to at least 5 mg/mL. This information has not been validated. Please see the link below to review a publication that may be of interest:
      https://www.ncbi.nlm.nih.gov/pmc/articles/PMC184764/

      Helpful?

  4. Does Product No  N5764, Nisin contain denatured milk solids?

    1 answer

    1. This product does not contain any milk solids

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