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Chemical Compound Review

Lanthionine     (2S)-2-amino-3-[(2S)-2-amino- 2-carboxy...

Synonyms: L-Lanthionine, Lanthionine L-, AG-F-06237, CHEBI:21347, CTK4G7812, ...
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Disease relevance of Lanthionine L-

  • Nisin is a small cationic lanthionine antibiotic produced by Lactococcus lactis [1].
  • They are characterized by the unique amino acids lanthionine and methyllanthionine, introduced by means of dehydration of Ser/Thr residues followed by reaction of the resulting dehydro amino acids with cysteines to form thioether linkages [2].
  • The lantibiotics are a rapidly expanding group of biologically active peptides produced by a variety of Gram-positive bacteria, and are so-called because of their content of the thioether amino acids lanthionine and beta-methyllanthionine [3].
  • In another mutagenesis study a double mutation was introduced in the nisZ gene by replacing the codons for Met-17 and Gly-18 by codons for Gln and Thr, respectively, as in the third lanthionine ring of the related antimicrobial peptide subtilin from Bacillus subtilis [4].
  • Demonstration of lanthionine as a natural constituent of the peptidoglycan of Fusobacterium nucleatum [5].

High impact information on Lanthionine L-

  • Lantibiotics are ribosomally synthesized oligopeptide antibiotics that contain lanthionine bridges derived by the posttranslational modification of amino acid residues [6].
  • Our results suggest that lantibiotic maturation and secretion occur at a membrane-associated multimeric lanthionine synthetase complex consisting of proteins NisB, NisC, and the ABC transporter molecules NisT [7].
  • Comparison of gene sequence homologies between nisin and the other lanthionine antibiotics, subtilin and epidermin, indicated that they all evolved from a common ancestor [8].
  • In this issue of Molecular Microbiology, Wiedemann and coworkers have made a big step towards understanding the mechanism of action of the two-component lanthionine-containing antibiotic lacticin 3147 [9].
  • Lan-7 is a novel, chemically stable peptide structurally related to somatostatin that contains a lanthionine bridge between the two cysteines in the peptide; TT-232 is a less stable analogue containing a disulfide bridge [10].

Chemical compound and disease context of Lanthionine L-


Biological context of Lanthionine L-


Anatomical context of Lanthionine L-


Associations of Lanthionine L- with other chemical compounds

  • [structure: see text] Lanthionine, a thioether analogue of cystine, is a key component of the lantibiotics, a family of modified peptides bearing multiple thioether bridges resulting from posttranslational modifications between side chains [19].
  • As previously described, ketimines arise from the deamination of a number of sulfur-containing amino acids, i.e. L-cystathionine, L-lanthionine and S-aminoethyl-L-cysteine, catalyzed by a widespread mammalian transaminase [20].
  • The NMR data were additionally confirmed by mass spectrometry and Edman degradation after chemical modification, which allowed sequencing of lanthionine and beta-methyllanthionine residues [21].
  • The SH groups could be completely alkylated at pH 7.6 in aqueous propanol, as shown by nearly quantitative recovery of lanthionine [22].

Gene context of Lanthionine L-

  • Therefore, lanthionine-based lipopeptide amides were synthesized and probed for activity as potential TLR2 agonists or antagonists [23].
  • LANCL1 (LanC-like protein 1) is related to the bacterial LanC (lanthionine synthetase C) family, which is involved in the biosynthesis of antimicrobial peptides [24].
  • Synthesis and biological activities of cyclic lanthionine enkephalin analogues: delta-opioid receptor selective ligands [25].
  • Electron capture induced dissociation (ECD) and collisionally activated dissociation (CAD) experiments were performed on four lanthionine bridge-containing antibiotics [26].
  • It was shown to be a 2,675-Da bacteriocin harboring a lanthionine structure [27].

Analytical, diagnostic and therapeutic context of Lanthionine L-

  • A new sulfur imino acid, 2H-1,4-thiazine-5,6-dihydro-3,5-dicarboxylic acid (lanthionine ketimine), has been detected in the bovine brain by means of fluorometric and HPLC procedures [28].


  1. Nisin-induced changes in Bacillus morphology suggest a paradigm of antibiotic action. Hyde, A.J., Parisot, J., McNichol, A., Bonev, B.B. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  2. Discovery and in vitro biosynthesis of haloduracin, a two-component lantibiotic. McClerren, A.L., Cooper, L.E., Quan, C., Thomas, P.M., Kelleher, N.L., van der Donk, W.A. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  3. The genetics of lantibiotic biosynthesis. Jack, R., Bierbaum, G., Heidrich, C., Sahl, H.G. Bioessays (1995) [Pubmed]
  4. Engineering dehydrated amino acid residues in the antimicrobial peptide nisin. Kuipers, O.P., Rollema, H.S., Yap, W.M., Boot, H.J., Siezen, R.J., de Vos, W.M. J. Biol. Chem. (1992) [Pubmed]
  5. Demonstration of lanthionine as a natural constituent of the peptidoglycan of Fusobacterium nucleatum. Vasstrand, E.N., Hofstad, T., Endresen, C., Jensen, H.B. Infect. Immun. (1979) [Pubmed]
  6. Cloning and engineering of the cinnamycin biosynthetic gene cluster from Streptomyces cinnamoneus cinnamoneus DSM 40005. Widdick, D.A., Dodd, H.M., Barraille, P., White, J., Stein, T.H., Chater, K.F., Gasson, M.J., Bibb, M.J. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  7. Biosynthesis of lantibiotic nisin. Posttranslational modification of its prepeptide occurs at a multimeric membrane-associated lanthionine synthetase complex. Siegers, K., Heinzmann, S., Entian, K.D. J. Biol. Chem. (1996) [Pubmed]
  8. Structure, expression, and evolution of a gene encoding the precursor of nisin, a small protein antibiotic. Buchman, G.W., Banerjee, S., Hansen, J.N. J. Biol. Chem. (1988) [Pubmed]
  9. A lesson in efficient killing from two-component lantibiotics. Breukink, E. Mol. Microbiol. (2006) [Pubmed]
  10. In vitro antineoplastic activity of a novel lanthionine-containing peptide. Zheng, H., Fink, D., Li, H., Jiang, X., Aebi, S., Law, P., Goodman, M., Howell, S.B. Clin. Cancer Res. (1997) [Pubmed]
  11. Cloning, sequencing and production of the lantibiotic mersacidin. Bierbaum, G., Brötz, H., Koller, K.P., Sahl, H.G. FEMS Microbiol. Lett. (1995) [Pubmed]
  12. Lanthionine-somatostatin analogs: synthesis, characterization, biological activity, and enzymatic stability studies. Osapay, G., Prokai, L., Kim, H.S., Medzihradszky, K.F., Coy, D.H., Liapakis, G., Reisine, T., Melacini, G., Zhu, Q., Wang, S.H., Mattern, R.H., Goodman, M. J. Med. Chem. (1997) [Pubmed]
  13. Biosynthesis of the lantibiotic mersacidin: organization of a type B lantibiotic gene cluster. Altena, K., Guder, A., Cramer, C., Bierbaum, G. Appl. Environ. Microbiol. (2000) [Pubmed]
  14. Evidence for production of a new lantibiotic (butyrivibriocin OR79A) by the ruminal anaerobe Butyrivibrio fibrisolvens OR79: characterization of the structural gene encoding butyrivibriocin OR79A. Kalmokoff, M.L., Lu, D., Whitford, M.F., Teather, R.M. Appl. Environ. Microbiol. (1999) [Pubmed]
  15. Two-component anti-Staphylococcus aureus lantibiotic activity produced by Staphylococcus aureus C55. Navaratna, M.A., Sahl, H.G., Tagg, J.R. Appl. Environ. Microbiol. (1998) [Pubmed]
  16. Characterization of rat LANCL1, a novel member of the lanthionine synthetase C-like protein family, highly expressed in testis and brain. Mayer, H., Bauer, H., Breuss, J., Ziegler, S., Prohaska, R. Gene (2001) [Pubmed]
  17. Detection of cystathionine ketimine and lanthionine ketimine in human brain. Fontana, M., Brunori, A., Costa, M., Antonucci, A. Neurochem. Res. (1997) [Pubmed]
  18. Lanthionine ketimine and S-(2-aminoethyl)-L-cysteine ketimine induce the tyrosyl phosphorylation of 45 kDa protein in parallel with its stimulation of superoxide generation in human neutrophils. Zhang, J., Sugahara, K., Hashimoto, K., Sagara, Y., Fontana, M., Duprè, S., Kodama, H. Physiological chemistry and physics and medical NMR. (1997) [Pubmed]
  19. Orthogonally protected lanthionines: synthesis and use for the solid-phase synthesis of an analogue of nisin ring C. Bregant, S., Tabor, A.B. J. Org. Chem. (2005) [Pubmed]
  20. Purification and characterization of a ketimine-reducing enzyme. Nardini, M., Ricci, G., Caccuri, A.M., Solinas, S.P., Vesci, L., Cavallini, D. Eur. J. Biochem. (1988) [Pubmed]
  21. The tetracyclic lantibiotic actagardine. 1H-NMR and 13C-NMR assignments and revised primary structure. Zimmermann, N., Metzger, J.W., Jung, G. Eur. J. Biochem. (1995) [Pubmed]
  22. Reactions of proteins with dehydroalanines. Friedman, M., Finley, J.W., Yeh, L.S. Adv. Exp. Med. Biol. (1977) [Pubmed]
  23. Lipolanthionine peptides act as inhibitors of TLR2-mediated IL-8 secretion. Synthesis and structure-activity relationships. Seyberth, T., Voss, S., Brock, R., Wiesmüller, K.H., Jung, G. J. Med. Chem. (2006) [Pubmed]
  24. Germ cell differentiation-dependent and stage-specific expression of LANCL1 in rodent testis. Nielsen, J.E., Hansen, M.A., Jørgensen, M., Tanaka, M., Almstrup, K., Skakkebaek, N.E., Leffers, H. European journal of histochemistry : EJH. (2003) [Pubmed]
  25. Synthesis and biological activities of cyclic lanthionine enkephalin analogues: delta-opioid receptor selective ligands. Rew, Y., Malkmus, S., Svensson, C., Yaksh, T.L., Chung, N.N., Schiller, P.W., Cassel, J.A., DeHaven, R.N., Taulane, J.P., Goodman, M. J. Med. Chem. (2002) [Pubmed]
  26. Localization of intramolecular monosulfide bridges in lantibiotics determined with electron capture induced dissociation. Kleinnijenhuis, A.J., Duursma, M.C., Breukink, E., Heeren, R.M., Heck, A.J. Anal. Chem. (2003) [Pubmed]
  27. Ruminococcin A, a new lantibiotic produced by a Ruminococcus gnavus strain isolated from human feces. Dabard, J., Bridonneau, C., Phillipe, C., Anglade, P., Molle, D., Nardi, M., Ladiré, M., Girardin, H., Marcille, F., Gomez, A., Fons, M. Appl. Environ. Microbiol. (2001) [Pubmed]
  28. Detection of 2H-1,4-thiazine-5,6-dihydro-3,5-dicarboxylic acid (lanthionine ketimine) in the bovine brain by a fluorometric assay. Ricci, G., Vesci, L., Nardini, M., Arduini, A., Storto, S., Rosato, N., Cavallini, D. Biochim. Biophys. Acta (1989) [Pubmed]
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