S-Aminoethyl-L-cysteine

S-Aminoethyl-l-cysteine
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
IUPAC name
S-(2-Aminoethyl)-L-cysteine
Systematic IUPAC name
(2R)-2-Amino-3-[(2-aminoethyl)sulfanyl]propanoic acid
Other names
Thialysine; L-3-[(2-Aminoethyl)thio]alanine; L-4-Thialysine; Thiosine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C5H12N2O2S/c6-1-2-10-3-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1 checkY
    Key: GHSJKUNUIHUPDF-BYPYZUCNSA-N checkY
  • InChI=1/C5H12N2O2S/c6-1-2-10-3-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1
    Key: GHSJKUNUIHUPDF-BYPYZUCNBP
  • OC([C@@H](N)CSCCN)=O
Properties
C5H12N2O2S
Molar mass 164.22 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

S-Aminoethyl-l-cysteine, also known as thialysine, is a toxic analog of the amino acid lysine in which the second carbon of the amino acid's R-group (side chain) has been replaced with a sulfur atom.

Strictly speaking, L-thialysine is actually considered an S-(2-aminoethyl) analogue of L-cysteine. This compound is known to have cytotoxic affects as it inhibits protein synthesis and lysine 2,3-aminomutase.[1]


References

  1. ^ "S-(2-Aminoethyl)-L-cysteine". pubchem.ncbi.nlm.nih.gov. Retrieved 5 February 2023.


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