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lanthionine
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Lanthionine is a nonproteinogenic amino acid with the chemical formula (HOOC-CH(NH2)-CH2-S-CH2-CH(NH2)-COOH). As the monosulfide analog of cystine, lanthionine is composed of two alanine residues that are crosslinked on their β-carbon atoms by a thioether linkage. Despite its name, lanthionine does not contain the element lanthanum.
==Background==
In 1941, lanthionine was first isolated from the treatment of wool with sodium carbonate〔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.〕 and was first synthesized from cysteine and β-chloroalanine.〔Brown, G. B.; du Vigneaud, V. (1941) The Stereoisomeric Forms of Lanthionine. ''Journal of Biological Chemistry'', ''140'', 767-771.〕 Lanthionines are found widely in nature and 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).〔Paul, M.; van der Donk, W. A. (2005) Chemical and Enzymatic Synthesis of Lanthionines. ''Mini-Reviews in Organic Chemistry'', ''2'', 23-37.〕〔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.〕
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