Lanthionine
Script error: No such module "Distinguish". <templatestyles src="Chembox/styles.css"/>
Template:Chembox image cellTemplate:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox Datapage checkTemplate:Chembox Footer| Template:Longitem | Template:Unbulleted list |
| ChEBI | Template:Unbulleted list |
| ChemSpider | Template:Unbulleted list |
| DrugBank | Template:Unbulleted list |
| EC Number | Template:Unbulleted list |
| KEGG | Template:Unbulleted list |
| Template:Longitem | Template:Unbulleted list |
| RTECS number | Template:Unbulleted list |
| Script error: No such module "collapsible list". | |
| Script error: No such module "collapsible list". | |
| Template:Longitem | C6H12N2O4S |
| Molar mass | 208.2318 g/mol |
| Melting point | Template:Chembox CalcTemperatures |
Template:Chembox Footer/trackingScript error: No such module "TemplatePar".Template:Short description
Lanthionine is a nonproteinogenic amino acid with the chemical formula (HOOC-CH(NH2)-CH2-S-CH2-CH(NH2)-COOH). It is typically formed by a cysteine residue and a dehydrated serine residue. Despite its name, lanthionine does not contain the element lanthanum.
Background
In 1941, lanthionine was first isolated by treating wool with sodium carbonate. It was found to be a sulfur-containing amino acid; accordingly it was given the name lanthionine [wool (Latin: Lana), sulfur (Greek: theîon)].[1] Lanthionine was first synthesized by alkylation of cysteine with β-chloroalanine.[2] Lanthionines are found widely in nature. They have been isolated from human hair, lactalbumin, and feathers. Lanthionines have also been found in bacterial cell walls and are the components of a group of gene-encoded peptide antibiotics called lantibiotics, which includes nisin (a food preservative), subtilin, epidermin (effective against Staphylococcus and Streptococcus), and ancovenin (an enzyme inhibitor).[3][4] Lanthionine is listed among novel uremic toxins, compounds elevated in blood of chronic kidney failure and uremic patiens.[5] It likely contributes to hyperhomocysteinemia and impaired hydrogen sulfide biosynthesis.[6] Lanthionine retention may also be linked to adverse cardiovascular outcomes as it can induce heart tissue fibrosis and promote vascular calcification.[7]
Preparation
A variety of syntheses of lanthionine have been published including sulfur extrusion from cystine,[8] ring opening of serine β-lactone,[4] and hetero-conjugate addition of cysteine to dehydroalanine.[9] The sulfur extrusion method is, however, the only pathway for lanthionine that has been employed in the total synthesis of a lantibiotic.
Biosynthesis of the lanthionine bridge in peptidic natural products can be accomplished through a number of different pathways. For example, the lanthionine bridges in the antibiotic nisin are the result of a dedicated dehydratase (NisB) and a dedicated cyclase (NisC).[10][11]
References
- ↑ Horn, M. J.; Jones, D. B.; Ringel, S. J. (1941) Isolation of a New Sulfur-Containing Amino Acid (Lanthionine) from Sodium Carbonate-Treated Wool. Journal of Biological Chemistry, 138, 141-149.
- ↑ Brown, G. B.; du Vigneaud, V. (1941) The Stereoisomeric Forms of Lanthionine. Journal of Biological Chemistry, 140, 767-771.
- ↑ Paul, M.; van der Donk, W. A. (2005) Chemical and Enzymatic Synthesis of Lanthionines. Mini-Reviews in Organic Chemistry, 2, 23-37.
- ↑ a b Shao, H.; Wang, S. H. H.; Lee, C.-W.; Ösapay, G.; Goodman, M. (1995) A Facile Synthesis of Orthogonally Protected Stereoisomeric Lanthionines by Regioselective Ring Opening of Serine β-Lactone Derivatives. Journal of Organic Chemistry, 60, 2956-2957.
- ↑ Garcia-Martinez Y, et al. Does gut microbiota dysbiosis impact the metabolic alterations of hydrogen sulfide and lanthionine in patients with chronic kidney disease ? BMC Microbiology 2024 10.1186/s12866-024-03590-0
- ↑ Perna AF, Di Nunzio A, Amoresano A, Pane F, Fontanarosa C, Pucci P, et al. Divergent behavior of hydrogen sulfide pools and of the sulfur metabolite lanthionine, a novel uremic toxin, in dialysis patients. Biochimie. 2016;126:97–107
- ↑ Coppola A, Vigorito C, Lombari P, Martínez YG, Borriello M, Trepiccione F, et al. Uremic Toxin Lanthionine induces endothelial cell mineralization in Vitro. Biomed. 2022;10:444.
- ↑ Harpp, D. N.; Gleason, J. G. (1971) Preparation and Mass Spectral Properties of Cystine and Lanthionine Derivatives. Novel Synthesis of L-Lanthionine by Selective Desulfurization. Journal of Organic Chemistry, 36, 73-80.
- ↑ Probert, J. M.; Rennex, D.; Bradley, M. (1996) Lanthionines for Solid Phase Synthesis. Tetrahedron Letters, 37, 1101-1104.
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".