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Lantibiotic lacticin-481

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Lantibiotic lacticin-481 is an antibacterial peptide isolated from Lactococcus lactis subsp. lactis. It has activity against gram-positive bacteria.

Category

Functional Peptides

Catalog number

BAT-012566

Molecular Formula

C127H182N36O35S4

Molecular Weight

2901.3

Specification
Reference Reading

IUPAC Name

(2R)-2-[[[(1S,5R,8Z,11S,14R,20R,23R,26R,29R,32R,35R,38R,43R,46S,51R,60S)-11,17-dibenzyl-46-[(2R)-butan-2-yl]-54-(2-carboxyethyl)-43-[[(2R)-2-[[(2S,3R)-2-[[(2R)-2-[[2-[[(2S)-2-[[2-[[2-[[(2R)-2,6-diamino-1-hydroxyhexylidene]amino]-1-hydroxyethylidene]amino]-1-hydroxyethylidene]amino]-1,3-dihydroxypropylidene]amino]-1-hydroxyethylidene]amino]-1-hydroxy-3-methylbutylidene]amino]-1-hydroxy-3-methylpentylidene]amino]-1-hydroxy-3-(1H-imidazol-5-yl)propylidene]amino]-8-ethylidene-7,10,13,16,19,22,25,28,31,34,37,44,47,49,52,55,62-heptadecahydroxy-29,35-bis(2-hydroxy-2-iminoethyl)-20-(3-hydroxy-3-iminopropyl)-51-(1H-imidazol-5-ylmethyl)-23-(1H-indol-3-ylmethyl)-32-(2-methylsulfanylethyl)-14-propan-2-yl-3,40,58-trithia-6,9,12,15,18,21,24,27,30,33,36,45,48,50,53,56,61-heptadecazatricyclo[36.10.8.65,26]dohexaconta-6,9,12,15,18,21,24,27,30,33,36,44,47,49,52,55,61-heptadecaen-60-yl]-hydroxymethylidene]amino]-3-hydroxypropanoic acid

Synonyms

Lys-Gly-Gly-Ser-Gly-Val-Ile-His-Thr-Ile-Ser-His-Glu-Cys-Asn-Met-Asn-Ser-Trp-Gln-Phe-Val-Phe-Thr-Cys-Cys-Ser

Sequence

KGGSGVIHTISHECNMNSWQFVFTCCS

InChI

InChI=1S/C127H182N36O35S4/c1-11-64(8)102-126(196)159-92-59-202-58-91-122(192)158-90(121(191)154-87(54-165)127(197)198)57-201-56-89(119(189)148-81(42-68-47-135-74-30-21-20-28-71(68)74)112(182)143-75(31-33-93(130)166)107(177)147-80(41-67-26-18-15-19-27-67)117(187)161-101(63(6)7)123(193)152-79(40-66-24-16-14-17-25-66)111(181)142-73(13-3)106(176)155-91)157-116(186)85(46-95(132)168)150-109(179)77(35-38-199-10)145-115(185)84(45-94(131)167)151-118(188)88(156-108(178)76(32-34-99(172)173)144-113(183)82(149-120(92)190)43-69-48-133-60-139-69)55-200-39-36-78(110(180)162-102)146-114(184)83(44-70-49-134-61-140-70)153-125(195)103(65(9)12-2)163-124(194)100(62(4)5)160-98(171)52-138-105(175)86(53-164)141-97(170)51-136-96(169)50-137-104(174)72(129)29-22-23-37-128/h13-21,24-28,30,47-49,60-65,72,75-92,100-103,135,164-165H,11-12,22-23,29,31-46,50-59,128-129H2,1-10H3,(H2,130,166)(H2,131,167)(H2,132,168)(H,133,139)(H,134,140)(H,136,169)(H,137,174)(H,138,175)(H,141,170)(H,142,181)(H,143,182)(H,144,183)(H,145,185)(H,146,184)(H,147,177)(H,148,189)(H,149,190)(H,150,179)(H,151,188)(H,152,193)(H,153,195)(H,154,191)(H,155,176)(H,156,178)(H,157,186)(H,158,192)(H,159,196)(H,160,171)(H,161,187)(H,162,180)(H,163,194)(H,172,173)(H,197,198)/b73-13-/t64-,65-,72-,75-,76?,77-,78-,79+,80?,81-,82-,83-,84-,85-,86+,87-,88+,89+,90-,91+,92-,100-,101-,102+,103+/m1/s1

InChI Key

UQTZYDQMZDLCFF-ZHVGFZBKSA-N

Canonical SMILES

CCC(C)C1C(=NC2CSCC3C(=NC(CSCC(C(=NC(C(=NC(C(=NC(C(=NC(C(=NC(C(=NC(=CC)C(=N3)O)O)CC4=CC=CC=C4)O)C(C)C)O)CC5=CC=CC=C5)O)CCC(=N)O)O)CC6=CNC7=CC=CC=C76)O)N=C(C(N=C(C(N=C(C(N=C(C(CSCCC(C(=N1)O)N=C(C(CC8=CN=CN8)N=C(C(C(C)CC)N=C(C(C(C)C)N=C(CN=C(C(CO)N=C(CN=C(CN=C(C(CCCCN)N)O)O)O)O)O)O)O)O)N=C(C(N=C(C(N=C2O)CC9=CN=CN9)O)CCC(=O)O)O)O)CC(=N)O)O)CCSC)O)CC(=N)O)O)C(=NC(CO)C(=O)O)O)O)O

1. Lacticin 481: in vitro reconstitution of lantibiotic synthetase activity

Lili Xie, Leah M Miller, Champak Chatterjee, Olga Averin, Neil L Kelleher, Wilfred A van der Donk Science. 2004 Jan 30;303(5658):679-81. doi: 10.1126/science.1092600.

The lantibiotic lacticin 481 is synthesized on ribosomes as a prepeptide (LctA) and posttranslationally modified to its mature form. These modifications include dehydration of serines and threonines, followed by intramolecular addition of cysteines to the unsaturated amino acids, which generates cyclic thioethers. This process breaks eight chemical bonds and forms six newbonds and is catalyzed by one enzyme, LctM. We have characterized the in vitro activity of LctM, which completely processed a series of LctA mutants, displaying a permissive substrate specificity that holds promise for antibiotic engineering.

2. Chemical synthesis of the lantibiotic lacticin 481 reveals the importance of lanthionine stereochemistry

Patrick J Knerr, Wilfred A van der Donk J Am Chem Soc. 2013 May 15;135(19):7094-7. doi: 10.1021/ja4014024. Epub 2013 May 3.

Lantibiotics are a family of antibacterial peptide natural products characterized by the post-translational installation of the thioether-containing amino acids lanthionine and methyllanthionine. Until recently, only a single naturally occurring stereochemical configuration for each of these cross-links was known. The discovery of lantibiotics with alternative lanthionine and methyllanthionine stereochemistry has prompted an investigation of its importance to biological activity. Here, solid-supported chemical synthesis enabled the total synthesis of the lantibiotic lacticin 481 and analogues containing cross-links with non-native stereochemical configurations. Biological evaluation revealed that these alterations abolished the antibacterial activity in all of the analogues, revealing the critical importance of the enzymatically installed stereochemistry for the biological activity of lacticin 481.

3. The structure of the lantibiotic lacticin 481 produced by Lactococcus lactis: location of the thioether bridges

H W van den Hooven, F M Lagerwerf, W Heerma, J Haverkamp, J C Piard, C W Hilbers, R J Siezen, O P Kuipers, H S Rollema FEBS Lett. 1996 Aug 12;391(3):317-22. doi: 10.1016/0014-5793(96)00771-5.

The lantibiotic lacticin 481 is a bacteriocin produced by Lactococcus lactis ssp. lactis. This polypeptide contains 27 amino acids, including the unusual residues dehydrobutyrine and the thioether-bridging lanthionine and 3-methyllanthionine. Lacticin 481 belongs to a structurally distinct group of lantibiotics, which also include streptococcin A-FF22, salivaricin A and variacin. Here we report the first complete structure of this type of lantibiotic. The exact location of the thioether bridges in lacticin 481 was determined by a combination of peptide chemistry, mass spectrometry and NMR spectroscopy, showing connections between residues 9 and 14, 11 and 25, and 18 and 26.