Everything about Lanthionine totally explained
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Lanthionine is a
nonproteinogenic amino acid with the chemical formula (HOOC-CH(NH
2)-CH
2-S-CH
2-CH(NH
2)-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 and was first synthesized from
cysteine and β-chloroalanine. 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).
Preparation
A variety of syntheses of lanthionine have been published including sulfur extrusion from cystine, ring opening of serine β-lactone, The sulfur extrusion method is, however, the only pathway for lanthionine that has been employed in the total synthesis of a lantibiotic.
Further Information
Get more info on 'Lanthionine'.
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