3D model (JSmol)
|Molar mass||208.2318 g/mol|
|Melting point||280 to 283 °C (536 to 541 °F; 553 to 556 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Lanthionine is a nonproteinogenic amino acid with the chemical formula (HOOC-CH(NH2)-CH2-S-CH2-CH(NH2)-COOH). It is a thioether dimer of cysteine, composed of two alanine residues that are crosslinked on their β-carbon via a sulfur atom. Despite its name, lanthionine does not contain the element lanthanum.
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)]. Lanthionine was first synthesized by alkylation of cysteine with β-chloroalanine. 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).
A variety of syntheses of lanthionine have been published including sulfur extrusion from cystine, ring opening of serine β-lactone, and hetero-conjugate addition of cysteine to dehydroalanine. 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 by 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).
- 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.
- 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.
- 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.
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