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Nisin

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

Category

Functional Peptides

Catalog number

BAT-010570

CAS number

1414-45-5

Molecular Formula

C143H230N42O37S7

Molecular Weight

3354.07

Specification
Reference Reading

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

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)

Appearance

Off-white Powder

Purity

98%

Density

1.4±0.1 g/cm3

Boiling Point

2966.8±65.0°C at 760 mmHg

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

Solubility

Soluble in DMSO

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

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

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.