Ethionine

Ethionine

Names
IUPAC name 2-Amino-4-ethylsulfanylbutyric acid
Other names S-Ethyl-L-homocysteine
Identifiers
CAS Number	13073-35-3  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:4886  N
ChEMBL	ChEMBL203187  N
ChemSpider	5970  Y
ECHA InfoCard	100.000.588
PubChem CID	6205
UNII	WX1BN24WZT  Y
CompTox Dashboard (EPA)	DTXSID0020579
InChI InChI=1S/C6H13NO2S/c1-2-10-4-3-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9) Y Key: GGLZPLKKBSSKCX-UHFFFAOYSA-N Y InChI=1/C6H13NO2S/c1-2-10-4-3-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9) Key: GGLZPLKKBSSKCX-UHFFFAOYAB
SMILES O=C(O)C(N)CCSCC
Properties
Chemical formula	C6H13NO2S
Molar mass	163.239 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

Ethionine is a non-proteinogenic amino acid structurally related to methionine, with an ethyl group in place of the methyl group.

Ethionine is an antimetabolite and methionine antagonist. It is a substrate for methionyl-tRNA synthetase and is incorporated into proteins. ^[1]

Ethionine has been found to naturally occur in the edible pulp of the durian fruit, and postulated to be a biosynthetic precursor for ethanethiol and other strong odorants found in the fruit. ^[2]

Older literature

• Narayan Shivapurkar, Mary J. Wilson and Lionel A. Poirier (1984). "Hypomethylation of DNA in ethionine-fed rats". Carcinogenesis. 5 (8): 989–992. doi:10.1093/carcin/5.8.989. PMID   6744518.
• Hoffman, Robert M. (1984). "Altered methionine metabolism, DNA methylation and oncogene expression in carcinogenesis". Biochimica et Biophysica Acta (BBA) - Reviews on Cancer. 738 (1–2): 49–87. doi:10.1016/0304-419x(84)90019-2. PMID   6204687.
• Fowden, L.; Lewis, D.; Tristram, H. (1967). "Toxic Amino Acids: Their Action as Antimetabolites". Advances in Enzymology and Related Areas of Molecular Biology. Vol. 29. pp. 89–163. doi:10.1002/9780470122747.ch3. ISBN   978-0-470-64958-9. PMID   4881886.

References

1. Rodgers, Kenneth J.; Shiozawa, Nae (2008). "Misincorporation of amino acid analogues into proteins by biosynthesis". The International Journal of Biochemistry & Cell Biology. 40 (8): 1452–1466. doi:10.1016/j.biocel.2008.01.009. PMID   18329946.
2. Nadine S. Fischer and Martin Steinhaus (2020). "Identification of an Important Odorant Precursor in Durian: First Evidence of Ethionine in Plants". Journal of Agricultural and Food Chemistry. 68 (38): 10397–10402. Bibcode:2020JAFC...6810397F. doi:10.1021/acs.jafc.9b07065. PMID   31825619. S2CID   209329891.