Lanthionine
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| Lanthionine | |
|---|---|
| Image:Lanthionine.png | |
| Identifiers | |
| CAS number | |
| PubChem | |
| Properties | |
| Molecular formula | C6H12N2O4S |
| Molar mass | 208.2318 g/mol |
| Melting point |
280-283 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
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.
Background
In 1941, lanthionine was first isolated from the treatment of wool with sodium carbonate[1] and was first synthesized from cysteine and β-chloroalanine.[2] 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 (an anti staphylococcus and streptococcus agent), and ancovenin (an enzyme inhibitor).[3][4]
Preparation
A variety of syntheses of lanthionine have been published including sulfur extrusion from cystine,[5] ring opening of serine β-lactone,[4] and Michael addition of cysteine to dehydroalanine.[6] The sulfur extrusion method is, however, the only pathway for lanthionine that has been employed in the total synthesis of a lantibiotic.
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.
- ↑ 4.0 4.1 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.
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
