Lanthionine
Identifiers
CAS number	[922-55-4]
PubChem	675804
Properties
Molecular formula	C6H12N2O4S
Molar mass	208. CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 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). The melting point of a solid is the temperature range at which it changes state from solid to Liquid. In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly Proteinogenic Amino acids also known as standard normal or primary amino acids are those 20 amino acids that are found in Proteins and that are coded for in the In Chemistry, an amino acid is a Molecule containing both Amine and Carboxyl Functional groups In Biochemistry, this 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. Cystine is the Amino acid Dimer formed when a pair of Cysteine molecules are joined by a Disulfide bond Alanine (abbreviated as Ala or A) is an α- Amino acid with the Chemical formula HO2CCH(NH2CH3 A thioether (similar to Sulfide) is a functional group in Organic chemistry that has the structure R1-S-R2 as shown on right

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. Wool is the fiber derived from the specialized skin cells called follicles of animals in the Caprinae family principally sheep, but the hair of certain species Sodium carbonate (also known as washing soda or soda ash), is a Sodium Salt of Carbonic acid. Not to be confused with Cystine, its oxidized dimer Cysteine (abbreviated as Cys or C) is an α- Amino acid with ^[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). Peptides (from the Greek πεπτίδια, "small digestibles" are short Polymers formed from the linking in a defined order of α- Amino Lantibiotics are a class of Peptide Antibiotics that contain polycyclic Thioether Amino acids as well as the unsaturated amino acids Nisin is a polycyclic Peptide antibacterial with 34 Amino acid residues used as a food Preservative. Staphylococcus (in Greek σταφυλη staphyle means bunch of grapes and κοκκος coccos means granule is a genus of Gram-positive Streptococcus is a Genus of spherical Gram-positive bacteria belonging to the phylum Firmicutes and the ^[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

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. The Journal of Biological Chemistry (often abbreviated JBC) is a Scientific journal founded in 1905 and published since 1925 by the American Society
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. The Journal of Organic Chemistry (abbreviated as J Org Chem or JOC) is a Scientific journal for original contributions of fundamental
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. Tetrahedron Letters is a weekly international journal for rapid publication of full original research papers in the field of Organic chemistry.