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L-lanthionine

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L-lanthionine

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Lanthionine is a nonproteinogenic amino acid with the chemical formula (HOOC-CH(NH2)-CH2-S-CH2-CH(NH2)-COOH). It is typically formed by a cysteine residue and a dehydrated serine residue. Despite its name, lanthionine does not contain the element lanthanum.

Chemical data

Formula
C6H12N2O4S
Molecular weight
208.24 g/mol
IUPAC name
(2R)-2-amino-3-[(2R)-2-amino-2-carboxyethyl]sulfanylpropanoic acid
SMILES
C([C@@H](C(=O)O)N)SC[C@@H](C(=O)O)N
InChIKey
DWPCPZJAHOETAG-IMJSIDKUSA-N
XLogP
-6.3
Polar surface area
152 Ų
H-bond donors
4
H-bond acceptors
7
Formal charge
0

via PubChem

Wikidata facts

Mass
208.051777864
Show 4 more facts
chemical formula
C₆H₁₂N₂O₄S
canonical SMILES
C(C(C(=O)O)N)SCC(C(=O)O)N
isomeric SMILES
C([C@@H](C(=O)O)N)SC[C@@H](C(=O)O)N
subject has role
primary metabolite
Sources (4)

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Encyclopedic overview

3 sections
Contents
  • Background
  • Preparation
  • References

Lanthionine is a nonproteinogenic amino acid with the chemical formula (HOOC-CH(NH2)-CH2-S-CH2-CH(NH2)-COOH). It is typically formed by a cysteine residue and a dehydrated serine residue. Despite its name, lanthionine does not contain the element lanthanum.

==Background==

Excerpted from Wikipedia’s “L-lanthionine” article, available under the CC BY-SA 4.0 licence.