Lanthionine

Lanthionine

Identifiers
CAS Number	922-55-4
ChEBI	CHEBI:21347
ChemSpider	88959
Jmol interactive 3D	Image
PubChem	256406
InChI InChI=1S/C6H12N2O4S/c7-3(5(9)10)1-13-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1 Key: DWPCPZJAHOETAG-IMJSIDKUSA-N InChI=1/C6H12N2O4S/c7-3(5(9)10)1-13-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1 Key: DWPCPZJAHOETAG-IMJSIDKUBX
SMILES O=C(O)[C@@H](N)CSC[C@H](N)C(=O)O
Properties
Chemical formula	C6H12N2O4S
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).
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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 the element lanthanum.

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 (effective against staphylococcus and streptococcus), 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 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

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. 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.