View source for Nisin

{{chembox
| verifiedrevid = 400327558
|ImageFile1=Nisin.png
|ImageSize1=250px
|ImageFile2=Nisin 1WCO.png
|ImageSize2=250px
|IUPACName=
|OtherNames=
|Section1={{Chembox Identifiers
|  InChI = 1/C143H246N42O45S7/c1-22-68(10)104(148)134(220)183-111(76(18)193)140(226)173-93(57-189)127(213)179-107(70(12)24-3)138(224)172-91(55-187)125(211)166-86(45-66(6)7)120(206)175-98(62-235)132(218)184-112(77(19)194)142(228)185-41-31-35-99(185)133(219)152-53-103(198)158-94(58-231)128(214)161-81(33-26-29-39-145)117(203)181-108(73(15)190)135(221)153-51-101(196)156-71(13)113(199)165-85(44-65(4)5)119(205)162-82(36-42-236-20)115(201)151-52-102(197)159-95(59-232)129(215)168-89(48-100(147)195)122(208)163-83(37-43-237-21)116(202)160-80(32-25-28-38-144)118(204)182-109(74(16)191)139(225)157-72(14)114(200)180-110(75(17)192)141(227)176-97(61-234)130(216)167-87(46-78-49-149-63-154-78)121(207)174-96(60-233)131(217)170-92(56-188)126(212)178-106(69(11)23-2)137(223)169-88(47-79-50-150-64-155-79)123(209)177-105(67(8)9)136(222)171-90(54-186)124(210)164-84(143(229)230)34-27-30-40-146/h49-50,63-77,80-99,104-112,186-194,231-235H,22-48,51-62,144-146,148H2,1-21H3,(H2,147,195)(H,149,154)(H,150,155)(H,151,201)(H,152,219)(H,153,221)(H,156,196)(H,157,225)(H,158,198)(H,159,197)(H,160,202)(H,161,214)(H,162,205)(H,163,208)(H,164,210)(H,165,199)(H,166,211)(H,167,216)(H,168,215)(H,169,223)(H,170,217)(H,171,222)(H,172,224)(H,173,226)(H,174,207)(H,175,206)(H,176,227)(H,177,209)(H,178,212)(H,179,213)(H,180,200)(H,181,203)(H,182,204)(H,183,220)(H,184,218)(H,229,230)
| InChIKey = WAMGWAJCUSJZNI-UHFFFAOYAB
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C143H246N42O45S7/c1-22-68(10)104(148)134(220)183-111(76(18)193)140(226)173-93(57-189)127(213)179-107(70(12)24-3)138(224)172-91(55-187)125(211)166-86(45-66(6)7)120(206)175-98(62-235)132(218)184-112(77(19)194)142(228)185-41-31-35-99(185)133(219)152-53-103(198)158-94(58-231)128(214)161-81(33-26-29-39-145)117(203)181-108(73(15)190)135(221)153-51-101(196)156-71(13)113(199)165-85(44-65(4)5)119(205)162-82(36-42-236-20)115(201)151-52-102(197)159-95(59-232)129(215)168-89(48-100(147)195)122(208)163-83(37-43-237-21)116(202)160-80(32-25-28-38-144)118(204)182-109(74(16)191)139(225)157-72(14)114(200)180-110(75(17)192)141(227)176-97(61-234)130(216)167-87(46-78-49-149-63-154-78)121(207)174-96(60-233)131(217)170-92(56-188)126(212)178-106(69(11)23-2)137(223)169-88(47-79-50-150-64-155-79)123(209)177-105(67(8)9)136(222)171-90(54-186)124(210)164-84(143(229)230)34-27-30-40-146/h49-50,63-77,80-99,104-112,186-194,231-235H,22-48,51-62,144-146,148H2,1-21H3,(H2,147,195)(H,149,154)(H,150,155)(H,151,201)(H,152,219)(H,153,221)(H,156,196)(H,157,225)(H,158,198)(H,159,197)(H,160,202)(H,161,214)(H,162,205)(H,163,208)(H,164,210)(H,165,199)(H,166,211)(H,167,216)(H,168,215)(H,169,223)(H,170,217)(H,171,222)(H,172,224)(H,173,226)(H,174,207)(H,175,206)(H,176,227)(H,177,209)(H,178,212)(H,179,213)(H,180,200)(H,181,203)(H,182,204)(H,183,220)(H,184,218)(H,229,230)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WAMGWAJCUSJZNI-UHFFFAOYSA-N
| CASNo=1414-45-5
|  PubChem=16219761
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID=21106355 
|  SMILES=C[C@H](CC)[C@@H](N)C(N/C(C(N[C@@H]1C(N[C@@H](C(NC(C(N[C@@H](C(N[C@@H](C(N[C@H](C(N2[C@@H](C(NC3)=O)CCC2)=O)[C@@H](C)SC[C@H](C(N[C@H](CCCCN)C(N[C@H](C(NCC(N[C@@H](C(N[C@H](CC(C)C)C(N[C@H](CCSC)C(NCC(N[C@@H](C(N[C@H](CC(N)=O)C(N[C@H](CCSC)C(N[C@H](CCCCN)C(N[C@@H]([C@@H](C)SC[C@@H](N6)C(N[C@H](CC5=CN=CN5)C(N[C@@H](C(N[C@H](CO)C(N[C@H]([C@@H](CC)C)C(N[C@H](CC8=CN=CN8)C(N[C@H]([C@@H](C)C)C(NC(C(N[C@H](CCCCN)C(O)=O)=O)=C)=O)=O)=O)=O)=O)CS[C@H](C)[C@H]7C6=O)=O)=O)C(N[C@H](C)C(N7)=O)=O)=O)=O)=O)=O)CS4)=O)=O)=O)=O)C)=O)=O)[C@H]4C)=O)=O)NC3=O)=O)CSC1)=O)CC(C)C)=O)=C)=O)[C@H](C)CC)=O)=O)=C\C)=O
  }}
|Section2={{Chembox Properties
|  Formula=C<sub>143</sub>H<sub>230</sub>N<sub>42</sub>O<sub>37</sub>S<sub>7</sub>
|  MolarMass=3354.07 g/mol
|  Appearance=
|  Density=
|  MeltingPt=
|  BoilingPt=
|  Solubility=
  }}
|Section3={{Chembox Hazards
|  MainHazards=
|  FlashPt=
|  Autoignition=
  }}
}}

'''Nisin''' is a polycyclic antibacterial [[peptide]] with 34 [[amino acid]] residues used as a food [[preservative]]. It contains the uncommon amino acids [[lanthionine]] (Lan), [[methyllanthionine]] (MeLan), [[didehydroalanine]] (Dha) and [[didehydroaminobutyric acid]] (Dhb). These unusual amino acids are introduced by [[posttranslational modification]] of the precursor peptide. In these reactions a [[ribosome|ribosomally]] synthesized 57-mer is converted to the final peptide. The unsaturated amino acids originate from [[serine]] and [[threonine]], and the enzyme-catalysed addition of [[cysteine]] residues to the didehydro amino acids result in the multiple thioether bridges.

Nisin is produced by fermentation using the [[bacterium]] ''[[Lactococcus]] lactis''. Commercially, it is obtained from the culturing of ''Lactoccus lactis'' on natural substrates, such as milk or dextrose, and is not chemically synthesized. It is used in processed [[cheese]], meats, beverages, etc. during production to extend shelf life by suppressing [[Gram-positive]] spoilage and pathogenic bacteria. While most [[bacteriocins]] generally inhibit only closely related species, Nisin is a rare example of a "broad-spectrum" bacteriocin effective against many Gram-positive organisms, including lactic acid bacteria (commonly associated with spoilage),'' [[Listeria monocytogenes]]'' (a known pathogen), etc.  However, when coupled with the chelator EDTA, Nisin has also been known to inhibit Gram-negative bacteria, as well.  Nisin is soluble in water and can be effective at levels nearing the parts per billion range.  In foods, it is common to use Nisin at levels ranging from ~1-25ppm, depending on the food type and regulatory approval.  Due to its naturally selective spectrum of activity, it is also employed as a selective agent in microbiological media for the isolation of gram-negative bacteria, yeast, and moulds. [[Subtilin]] and [[Epidermin]] are related to Nisin.  All are members of a class of molecules known as [[lantibiotics]].

As a [[food additive]], nisin has [[E number]] E234.

== Further reading ==

* K. Fukase et al., Tetrahedron Lett. 1988, 29, 7, 795. ([[Total synthesis]])
* G. W. Buchman et al., J. Biol. Chem. 1988, 263, 31, 16260. ([[Biosynthesis]])

== External links ==
* [http://bactibase.pfba-lab-tun.org/BAC047 Nisin A]
* [http://bactibase.pfba-lab-tun.org/BAC049 Nisin Z]
* [http://bactibase.pfba-lab-tun.org/BAC145 Nisin Q]
* [http://bactibase.pfba-lab-tun.org/BAC146 Nisin F]
* [http://bactibase.pfba-lab-tun.org/BAC147 Nisin U]

{{Pore-forming toxins}}
[[Category:Lantibiotics]]
[[Category:Preservatives]]
[[Category:Peripheral membrane proteins]]

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[[pl:Nizyna]]
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