Nisin A

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Nisin A
Category Antibiotics
Catalog number BBF-03772
CAS 1414-45-5
Molecular Weight 3354.07
Molecular Formula C143H230N42O37S7

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Description

Nisin A is a polycyclic antibacterial peptide produced by the bacterium Lactococcus lactis that is used as a food preservative.

Specification

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-lysinecyclic(3->7),(8->11),(13->19),(23->26),(25->28)-pentakis(sulfide); Ile-Abu-d-Cys-Ile-Ala-Leu-Cys-d-Abu-Pro-Gly-Cys-Lys-d-Abu-Gly-Ala-Leu-Met-Gly-Cys-Asn-Met-Lys-d-Abu-Ala-d-Abu-Cys-His-Cys-Ser-Ile-His-Val-Ala-Lys (Disulfide bridge: Cys3-Cys7, Abu8-Cys11, Abu13-Cys19, Abu23-Cys26, Abu25-Cys28)
Sequence I-Abu-d-Cys-IALC-d-Abu-PGCK-d-Abu-GALMGCNML-d-Abu-A-d-Abu-CHCSIHVAK (Disulfide bridge: Cys3-Cys7, Abu8-Cys11, Abu13-Cys19, Abu23-Cys26, Abu25-Cys28)
Storage Store at -20°C
IUPAC Name (2S)-6-amino-2-[2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(1R,4S,7R,11R,14S,17R)-7-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-4-amino-2-[[(3R,9S,12S,15S,21S)-21-[[(2R)-6-amino-2-[[(3R,7R,13S)-3-[[(3R,6S,12S,15R)-15-[[(E)-2-[[(2S,3S)-2-amino-3-methylpentanoyl]amino]but-2-enoyl]amino]-12-[(2S)-butan-2-yl]-9-methylidene-6-(2-methylpropyl)-5,8,11,14-tetraoxo-1-thia-4,7,10,13-tetrazacyclohexadecane-3-carbonyl]amino]-4-methyl-2,9,12-trioxo-5-thia-1,8,11-triazabicyclo[11.3.0]hexadecane-7-carbonyl]amino]hexanoyl]amino]-15,22-dimethyl-12-(2-methylpropyl)-9-(2-methylsulfanylethyl)-5,8,11,14,17,20-hexaoxo-1-thia-4,7,10,13,16,19-hexazacyclodocosane-3-carbonyl]amino]-4-oxobutanoyl]amino]-4-methylsulfanylbutanoyl]amino]hexanoyl]amino]-14-(1H-imidazol-5-ylmethyl)-4,8,20-trimethyl-3,6,12,15,21-pentaoxo-9,19-dithia-2,5,13,16,22-pentazabicyclo[9.9.2]docosane-17-carbonyl]amino]-3-hydroxypropanoyl]amino]-3-methylpentanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-3-methylbutanoyl]amino]prop-2-enoylamino]hexanoic acid
Canonical SMILES CCC(C)C1C(=O)NC(=C)C(=O)NC(C(=O)NC(CSCC(C(=O)N1)NC(=O)C(=CC)NC(=O)C(C(C)CC)N)C(=O)NC2C(SCC(NC(=O)CNC(=O)C3CCCN3C2=O)C(=O)NC(CCCCN)C(=O)NC4C(SCC(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC4=O)C)CC(C)C)CCSC)C(=O)NC(CC(=O)N)C(=O)NC(CCSC)C(=O)NC(CCCCN)C(=O)NC5C(SCC6C(=O)NC(C(=O)NC(CSC(C(C(=O)N6)NC(=O)C(NC5=O)C)C)C(=O)NC(CO)C(=O)NC(C(C)CC)C(=O)NC(CC7=CN=CN7)C(=O)NC(C(C)C)C(=O)NC(=C)C(=O)NC(CCCCN)C(=O)O)CC8=CN=CN8)C)C)C)CC(C)C
InChI 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
Source Lactococcus Lactis

Properties

Appearance Off-white Powder
Application

Nisin is a natural antimicrobial peptide that has attracted great attention in the food industry and biotechnology due to its potent antimicrobial properties and versatility. This 34 amino acid peptide is produced by certain strains of lactic acid bacteria, particularly Lactococcus lactis subsp. nisin has been approved for use as a food preservative in many countries and is known for its ability to inhibit the growth of a wide range of Gram-positive bacteria, including foodborne pathogens such as Listeria monocytogenes and Staphylococcus aureus.

Food Preservation: Nisin is mostly utilized as a safe, natural preservative to increase the shelf life and safety of a variety of foods. It works well to prevent the formation of spoilage and pathogenic germs, which makes it a desirable substitute for artificial preservatives. Nisin can be applied topically to food packaging materials or added straight to food.

Applications in Biotechnology: Nisin has applications not just in food preservation but also in the biotechnology and pharmaceutical sectors. Nisin is a key element in the creation of antimicrobial agents for a range of applications due to its strong antibacterial capabilities. To stop infections on medical implants, catheters, and other equipment, antimicrobial coatings based on nisin can be used. Nisin is being researched in the pharmaceutical sector for its possible application in fighting bacteria that are resistant to drugs. Nisin is also utilized in biopreservation, a process that prolongs the shelf life of biomaterials including probiotics, enzymes, and vaccines by utilizing natural antimicrobials. Nisin can be added to biopreservative formulations to increase the products' stability and effectiveness.

Biomedical Applications: Nisin's antibacterial qualities have generated curiosity in its possible uses in biomedical studies. Research has demonstrated that nisin's ability to induce apoptosis in cancer cells demonstrates its anticancer efficacy. Nisin's anti-inflammatory qualities have also been researched in relation to the management of inflammatory bowel disease.
Antibiotic Activity Spectrum Gram-positive bacteria
Boiling Point 2966.8±65.0°C at 760 mmHg
Density 1.4±0.1 g/cm3
Solubility Soluble in DMSO

Reference Reading

1. Nisin resistance in Gram-positive bacteria and approaches to circumvent resistance for successful therapeutic use
César Matos Ribeiro da Silva, Marcelo Rodrigues de Melo, Ana Andréa Teixeira Barbosa, Sona Jain, Silvio Santana Dolabella Crit Rev Microbiol . 2021 May;47(3):376-385. doi: 10.1080/1040841X.2021.1893264.
Antibiotic resistance among bacterial pathogens is one of the most worrying problems in health systems today. To solve this problem, bacteriocins from lactic acid bacteria, especially nisin, have been proposed as an alternative for controlling multidrug-resistant bacteria. Bacteriocins are antimicrobial peptides that have activity mainly against Gram-positive strains. Nisin is one of the most studied bacteriocins and is already approved for use in food preservation. Nisin is still not approved for human clinical use, but manyin vitrostudies have shown its therapeutic effectiveness, especially for the control of antibiotic-resistant strains. Results fromin vitrostudies show the emergence of nisin-resistant bacteria after exposure to nisin. Considering that nisin has shown promising results for clinical use, studies to elucidate nisin-resistant mechanisms and the development of approaches to circumvent nisin-resistance are important. Thus, the objectives of this review are to identify the Gram-positive bacterial strains that have shown resistance to nisin, describe their resistance mechanisms and propose ways to overcome the development of nisin-resistance for its successful clinical application.
2. Nisin as a Food Preservative: Part 1: Physicochemical Properties, Antimicrobial Activity, and Main Uses
Pascal Degraeve, Adem Gharsallaoui, Catherine Joly, Nadia Oulahal Crit Rev Food Sci Nutr . 2016 Jun 10;56(8):1262-74. doi: 10.1080/10408398.2013.763765.
Nisin is a natural preservative for many food products. This bacteriocin is mainly used in dairy and meat products. Nisin inhibits pathogenic food borne bacteria such as Listeria monocytogenes and many other Gram-positive food spoilage microorganisms. Nisin can be used alone or in combination with other preservatives or also with several physical treatments. This paper reviews physicochemical and biological properties of nisin, the main factors affecting its antimicrobial effectiveness, and its food applications as an additive directly incorporated into food matrices.
3. Nisin biosynthesis and its properties
Chan-Ick Cheigh, Yu-Ryang Pyun Biotechnol Lett . 2005 Nov;27(21):1641-8. doi: 10.1007/s10529-005-2721-x.
The antimicrobial peptide, nisin, produced by several strains of Lactococcus lactis, which belongs to the Class I bacteriocins called lantibiotics, is a small (3.4 kDa), 34-amino acid, cationic, hydrophobic peptide and has the five characteristic (beta-methyl)lanthionine rings formed by significant post-translational modification. A cluster of 11 genes has been involved in the biosynthesis of nisin and are proposed to be transcriptionally arranged as nisA(Z)BTCIP, nisRK, and nisFEG. The biosynthesis of nisin is regulated in a growth-phase-dependent manner including nisin-mediated induction which occurs via NisRK two-component regulatory system. This review outlines some of the more recent developments in the properties, regulation and applications of nisin biosynthesis.

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