Lanthionine

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Structural formula
Lanthionine
Structural formula of L -lanthionine
General
Surname Lanthionine
other names
  • 3,3'-thiodialanine
  • 3,3'-thiobis-2-aminopropionic acid
  • ( R , R ) -3,3'-thiodialanine
  • ( R , R ) -3,3′-thiobis-2-aminopropionic acid
Molecular formula C 6 H 12 N 2 O 4 S
External identifiers / databases
CAS number
  • 922-55-4 ( L -lanthionine)
  • 3183-08-2 ( DL -lanthionine)
  • 5965-92-4 ( D -lanthionine)
EC number 213-076-7
ECHA InfoCard 100,011,888
PubChem 98504
ChemSpider 88959
Wikidata Q417755
properties
Molar mass 208.24 g mol −1
Physical state

firmly

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Lanthionine is a non-proteinogenic amino acid that is related to cystine .

Occurrence and extraction

Sheep wool before processing

It is found in hair, wool, and feathers, but has also been found in bacterial cell walls . Lanthionine was first isolated in 1941 when wool was treated with sodium carbonate .

synthesis

Lanthionine can be formed from the amino acids cysteine and dehydroalanine through an addition. A synthesis from cysteine ​​and β-chloralanine also leads to lanthionine.

meaning

A group of peptide antibiotics is derived from lanthionine : the lantibiotics . These include mersacidin , nisin , subtilin , epidermin and ancovenin .

Individual evidence

  1. ↑ a b data sheet DL-Lanthionine from Sigma-Aldrich , accessed on April 7, 2011 ( PDF ).