Lanthionine

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Not to be confused with Lenthionine or Lanthanide.
Lanthionine
Lanthionine.png
Identifiers
CAS number 922-55-4 YesY
PubChem 256406
ChemSpider 88959 YesY
ChEBI CHEBI:21347 YesY
Jmol-3D images Image 1
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 (77 °F), 100 kPa)
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Infobox 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. Despite its name, lanthionine does not contain lanthanum.

Background[edit]

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[edit]

A variety of syntheses of lanthionine have been published including sulfur extrusion from cystine,[5] ring opening of serine β-lactone,[4] and hetero-conjugate 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[edit]

  1. ^ 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.
  2. ^ Brown, G. B.; du Vigneaud, V. (1941) The Stereoisomeric Forms of Lanthionine. Journal of Biological Chemistry, 140, 767-771.
  3. ^ Paul, M.; van der Donk, W. A. (2005) Chemical and Enzymatic Synthesis of Lanthionines. Mini-Reviews in Organic Chemistry, 2, 23-37.
  4. ^ 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.
  5. ^ 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.
  6. ^ Probert, J. M.; Rennex, D.; Bradley, M. (1996) Lanthionines for Solid Phase Synthesis. Tetrahedron Letters, 37, 1101-1104.