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Pediocin PA-1

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Pediocin PA-1 is a wide-spectrum bacteriocin from lactic acid bacteria that shows a particularly strong activity against Listeria monocytogenes. This antimicrobial peptide is the most extensively studied class Ila (or pediocin family) bacteriocin, and it is used as a food biopreservative.

Category

Functional Peptides

Catalog number

BAT-011620

CAS number

111745-56-3

Molecular Formula

C196H293N61O60S5

Molecular Weight

4624.12

Specification
Reference Reading

IUPAC Name

(4R,7S,10S,13S,19S,22S,31S,34S,37S,40S,43S,46S,52S,55S,58S,61S,64R)-64-[[(2S,3R)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-6-amino-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(4R,7S,10S,13S,19R)-13-(4-aminobutyl)-19-[[(2S,3R)-2-[[(2S)-2-[[2-[[(2S)-4-amino-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2,6-diaminohexanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]-4-oxobutanoyl]amino]acetyl]amino]-3-methylbutanoyl]amino]-3-hydroxybutanoyl]amino]-7-(hydroxymethyl)-10-(1H-imidazol-5-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]amino]-3-hydroxypropanoyl]amino]-3-methylbutanoyl]amino]-3-carboxypropanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]acetyl]amino]hexanoyl]amino]propanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxybutanoyl]amino]-7-(4-aminobutyl)-13,52,55-tris(2-amino-2-oxoethyl)-19-(3-amino-3-oxopropyl)-58,61-bis[(2S)-butan-2-yl]-31-[(1R)-1-hydroxyethyl]-10,22-bis(1H-imidazol-5-ylmethyl)-37-(1H-indol-3-ylmethyl)-34,40,46-trimethyl-43-(2-methylsulfanylethyl)-6,9,12,15,18,21,24,27,30,33,36,39,42,45,48,51,54,57,60,63-icosaoxo-1,2-dithia-5,8,11,14,17,20,23,26,29,32,35,38,41,44,47,50,53,56,59,62-icosazacyclopentahexacontane-4-carboxylic acid

Synonyms

Pediocin PA 1; H-Lys-Tyr-Tyr-Gly-Asn-Gly-Val-Thr-Cys(1)-Gly-Lys-His-Ser-Cys(1)-Ser-Val-Asp-Trp-Gly-Lys-Ala-Thr-Thr-Cys(2)-Ile-Ile-Asn-Asn-Gly-Ala-Met-Ala-Trp-Ala-Thr-Gly-Gly-His-Gln-Gly-Asn-His-Lys-Cys(2)-OH; L-lysyl-L-tyrosyl-L-tyrosyl-glycyl-L-asparagyl-glycyl-L-valyl-L-threonyl-L-cysteinyl-glycyl-L-lysyl-L-histidyl-L-seryl-L-cysteinyl-L-seryl-L-valyl-L-alpha-aspartyl-L-tryptophyl-glycyl-L-lysyl-L-alanyl-L-threonyl-L-threonyl-L-cysteinyl-L-isoleucyl-L-isoleucyl-L-asparagyl-L-asparagyl-glycyl-L-alanyl-L-methionyl-L-alanyl-L-tryptophyl-L-alanyl-L-threonyl-glycyl-glycyl-L-histidyl-L-glutaminyl-glycyl-L-asparagyl-L-histidyl-L-lysyl-L-cysteine (9->14),(24->44)-bis(disulfide)

Purity

>98%

Sequence

KYYGNGVTCGKHSCSVDWGKATTCIINNGAMAWATGGHQGNHKC (Disulfide bridge: Cys9-Cys14, Cys24-Cys44)

Storage

Store at -20°C

InChI

InChI=1S/C196H293N61O60S5/c1-18-92(7)155-191(311)242-131(66-143(206)270)182(302)241-129(64-141(204)268)170(290)214-75-145(272)223-94(9)161(281)232-120(50-55-318-17)173(293)224-95(10)162(282)235-124(59-105-69-211-115-36-23-21-33-112(105)115)176(296)226-97(12)163(283)254-157(98(13)260)188(308)219-73-144(271)212-74-146(273)229-125(60-106-70-207-87-220-106)178(298)234-119(48-49-139(202)266)166(286)213-78-150(277)231-130(65-142(205)269)181(301)240-126(61-107-71-208-88-221-107)179(299)233-118(39-27-31-54-200)175(295)249-138(196(316)317)86-322-321-85-137(187(307)252-156(93(8)19-2)192(312)253-155)248-194(314)159(100(15)262)257-195(315)160(101(16)263)255-164(284)96(11)225-172(292)116(37-25-29-52-198)227-147(274)76-216-168(288)123(58-104-68-210-114-35-22-20-32-111(104)114)238-183(303)132(67-152(279)280)243-189(309)154(91(5)6)251-185(305)134(82-259)245-186(306)136-84-320-319-83-135(171(291)218-77-148(275)228-117(38-26-30-53-199)174(294)239-127(62-108-72-209-89-222-108)180(300)244-133(81-258)184(304)246-136)247-193(313)158(99(14)261)256-190(310)153(90(3)4)250-151(278)80-217-169(289)128(63-140(203)267)230-149(276)79-215-167(287)121(56-102-40-44-109(264)45-41-102)237-177(297)122(57-103-42-46-110(265)47-43-103)236-165(285)113(201)34-24-28-51-197/h20-23,32-33,35-36,40-47,68-72,87-101,113,116-138,153-160,210-211,258-265H,18-19,24-31,34,37-39,48-67,73-86,197-201H2,1-17H3,(H2,202,266)(H2,203,267)(H2,204,268)(H2,205,269)(H2,206,270)(H,207,220)(H,208,221)(H,209,222)(H,212,271)(H,213,286)(H,214,290)(H,215,287)(H,216,288)(H,217,289)(H,218,291)(H,219,308)(H,223,272)(H,224,293)(H,225,292)(H,226,296)(H,227,274)(H,228,275)(H,229,273)(H,230,276)(H,231,277)(H,232,281)(H,233,299)(H,234,298)(H,235,282)(H,236,285)(H,237,297)(H,238,303)(H,239,294)(H,240,301)(H,241,302)(H,242,311)(H,243,309)(H,244,300)(H,245,306)(H,246,304)(H,247,313)(H,248,314)(H,249,295)(H,250,278)(H,251,305)(H,252,307)(H,253,312)(H,254,283)(H,255,284)(H,256,310)(H,257,315)(H,279,280)(H,316,317)/t92-,93-,94-,95-,96-,97-,98+,99+,100+,101+,113-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,138-,153-,154-,155-,156-,157-,158-,159-,160-/m0/s1

InChI Key

ZRUMXHGBGLWVDT-SJMRFLIKSA-N

Canonical SMILES

CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NCC(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(CSSCC(C(=O)N1)NC(=O)C(C(C)O)NC(=O)C(C(C)O)NC(=O)C(C)NC(=O)C(CCCCN)NC(=O)CNC(=O)C(CC2=CNC3=CC=CC=C32)NC(=O)C(CC(=O)O)NC(=O)C(C(C)C)NC(=O)C(CO)NC(=O)C4CSSCC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)N4)CO)CC5=CN=CN5)CCCCN)NC(=O)C(C(C)O)NC(=O)C(C(C)C)NC(=O)CNC(=O)C(CC(=O)N)NC(=O)CNC(=O)C(CC6=CC=C(C=C6)O)NC(=O)C(CC7=CC=C(C=C7)O)NC(=O)C(CCCCN)N)C(=O)O)CCCCN)CC8=CN=CN8)CC(=O)N)CCC(=O)N)CC9=CN=CN9)C(C)O)C)CC1=CNC2=CC=CC=C21)C)CCSC)C)CC(=O)N)CC(=O)N)C(C)CC

1. Establishing recombinant production of pediocin PA-1 in Corynebacterium glutamicum

Oliver Goldbeck, et al. Metab Eng. 2021 Nov;68:34-45. doi: 10.1016/j.ymben.2021.09.002. Epub 2021 Sep 4.

Bacteriocins are antimicrobial peptides produced by bacteria to inhibit competitors in their natural environments. Some of these peptides have emerged as commercial food preservatives and, due to the rapid increase in antibiotic resistant bacteria, are also discussed as interesting alternatives to antibiotics for therapeutic purposes. Currently, commercial bacteriocins are produced exclusively with natural producer organisms on complex substrates and are sold as semi-purified preparations or crude fermentates. To allow clinical application, efficacy of production and purity of the product need to be improved. This can be achieved by shifting production to recombinant microorganisms. Here, we identify Corynebacterium glutamicum as a suitable production host for the bacteriocin pediocin PA-1. C. glutamicum CR099 shows resistance to high concentrations of pediocin PA-1 and the bacteriocin was not inactivated when spiked into growing cultures of this bacterium. Recombinant C. glutamicum expressing a synthetic pedACDCgl operon releases a compound that has potent antimicrobial activity against Listeria monocytogenes and Listeria innocua and matches size and mass:charge ratio of commercial pediocin PA-1. Fermentations in shake flasks and bioreactors suggest that low levels of dissolved oxygen are favorable for production of pediocin. Under these conditions, however, reduced activity of the TCA cycle resulted in decreased availability of the important pediocin precursor l-asparagine suggesting options for further improvement. Overall, we demonstrate that C. glutamicum is a suitable host for recombinant production of bacteriocins of the pediocin family.

2. Pediocin PA-1, a wide-spectrum bacteriocin from lactic acid bacteria

Juan M Rodríguez, María I Martínez, Jan Kok Crit Rev Food Sci Nutr. 2002 Mar;42(2):91-121. doi: 10.1080/10408690290825475.

Pediocin PA-1 is a broad-spectrum lactic acid bacteria bacteriocin that shows a particularly strong activity against Listeria monocytogenes, a foodborne pathogen of special concern among the food industries. This antimicrobial peptide is the most extensively studied class Ila (or pediocin family) bacteriocin, and it has been sufficiently well characterized to be used as a food biopreservative. This review focuses on the progress that have been made in the elucidation of its structure, mode of action, and biosynthesis, and includes an overview of its applications in food systems. The aspects that need further research are also addressed. In the future, protein engineering, genetic engineering and/or chemical synthesis may lead to the development of new antimicrobial peptides with improved properties, based on some features of the pediocin PA-1 molecule.

3. An oxidation resistant pediocin PA-1 derivative and penocin A display effective anti- Listeria activity in a model human gut environment

Taís M Kuniyoshi, et al. Gut Microbes. 2022 Jan-Dec;14(1):2004071. doi: 10.1080/19490976.2021.2004071.

Pediocin PA-1 is a class IIa bacteriocin that is particularly effective against the foodborne pathogen Listeria monocytogenes. The loss of activity of PA-1 pediocin due to methionine oxidation is one of the challenges that limit the wider application of the bacteriocin. In this study, we heterologously expressed an oxidation resistant form of pediocin PA-1, i.e., pediocin M31L, and compared its activity to that of native pediocin PA-1 and to penocin A, a pediocin-like bacteriocin that displays a narrower antimicrobial spectrum. Minimal inhibitory concentration assays revealed that pediocin M31L was as effective as PA-1 and more effective than synthetic penocin A against Listeria with negligible activity against a range of obligate anaerobic commensal gut bacterial species. The anti-Listeria activity of these pediocins was also assessed in a simulated human distal colon model assay using the L. monocytogenes, spiked at 6.5 ± 0.13 Log CFU/mL, as a bioindicator. At 24 h, pediocin M31L and penocin A (2.6 μM) reduced Listeria counts to 3.5 ± 0.4 and 3.64 ± 0.62 Log CFU/mL, respectively, whereas Listeria counts were considerably higher, i.e. 7.75 ± 0.43 Log CFU/mL, in the non-bacteriocin-containing control. Ultimately, it was established that synthetic penocin A and the stable pediocin M31L derivative, heterologously produced, display effective anti-Listeria activity in a human gut environment.