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Ethionine

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

Ethionine
Names
IUPAC name
2-Amino-4-ethylsulfanylbutyric acid
Other names
S-Ethyl-L-homocysteine
Identifiers
  • 13073-35-3 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:4886 N
ChEMBL
  • ChEMBL203187 N
ChemSpider
  • 5970 Y
ECHA InfoCard 100.000.588
  • 6205
UNII
  • WX1BN24WZT Y
  • DTXSID0020579
  • 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
  • O=C(O)C(N)CCSCC
Properties
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 ?)

Ethionine is an antimetabolite and methionine antagonist. It prevents amino acid incorporation into proteins and interferes with cellular use of adenosine triphosphate (ATP). Because of these pharmacological effects, ethionine is highly toxic and is a potent carcinogen.[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]

References edit

  1. ^ 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.
  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. doi:10.1021/acs.jafc.9b07065. PMID 31825619. S2CID 209329891.

ethionine, proteinogenic, amino, acid, structurally, related, methionine, with, ethyl, group, place, methyl, group, names, iupac, name, amino, ethylsulfanylbutyric, acid, other, names, ethyl, homocysteine, identifiers, number, 13073, model, jsmol, interactive,. Ethionine is a non proteinogenic amino acid structurally related to methionine with an ethyl group in place of the methyl group 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 YKey GGLZPLKKBSSKCX UHFFFAOYSA N YInChI 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 Y N Infobox references Ethionine is an antimetabolite and methionine antagonist It prevents amino acid incorporation into proteins and interferes with cellular use of adenosine triphosphate ATP Because of these pharmacological effects ethionine is highly toxic and is a potent carcinogen 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 References edit 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 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 doi 10 1021 acs jafc 9b07065 PMID 31825619 S2CID 209329891 nbsp This article about an amine is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Ethionine amp oldid 1175853172, wikipedia, wiki, book, books, library,

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