Methionine

Methionine
Chemical structure of methionine
Skeletal formula of the canonical form of methionine
Names
IUPAC name
Methionine
Other names
2-amino-4-(methylthio)butanoic acid
Identifiers
3D model (JSmol)
Abbreviations Met, M
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.393 Edit this at Wikidata
EC Number
  • L: 200-432-1
KEGG
UNII
  • InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1 checkY
    Key: FFEARJCKVFRZRR-BYPYZUCNSA-N checkY
  • D/L: Key: FFEARJCKVFRZRR-UHFFFAOYSA-N
  • D: Key: FFEARJCKVFRZRR-SCSAIBSYSA-N
  • L: CSCC[C@H](N)C(=O)O
  • L Zwitterion: CSCC[C@H]([NH3+])C(=O)[O-]
Properties[2]
C5H11NO2S
Molar mass 149.21 g·mol−1
Appearance White crystalline powder
Density 1.340 g/cm3
Melting point 281 °C (538 °F; 554 K) decomposes
Soluble
Acidity (pKa) 2.28 (carboxyl), 9.21 (amino)[1]
Pharmacology
V03AB26 (WHO) QA05BA90 (WHO), QG04BA90 (WHO)
Supplementary data page
Methionine (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Methionine (symbol Met or M)[3] (/mɪˈθənn/)[4] is an essential amino acid in humans.

As the precursor of other non-essential amino acids such as cysteine and taurine, versatile compounds such as SAM-e, and the important antioxidant glutathione, methionine plays a critical role in the metabolism and health of many species, including humans. Methionine is also involved in angiogenesis and various processes related to DNA transcription, epigenetic expression, and gene regulation.

Methionine was first isolated in 1921 by John Howard Mueller.[5] It is encoded by the codon AUG. It was named by Satoru Odake in 1925, as an abbreviation of its structural description 2-amino-4-(methylthio)butanoic acid.[6]

  1. ^ Dawson RM, Elliott DC, Elliott WH, Jones KM (1959). Data for Biochemical Research. Oxford: Clarendon Press.
  2. ^ Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-374. ISBN 0-8493-0462-8..
  3. ^ "Nomenclature and Symbolism for Amino Acids and Peptides". IUPAC-IUB Joint Commission on Biochemical Nomenclature. 1983. Archived from the original on 9 October 2008. Retrieved 5 March 2018.
  4. ^ "Methionine". Oxford University Press. Archived from the original on January 27, 2018.
  5. ^ Pappenheimer AM (1987). "A Biographical Memoir of John Howard Mueller" (PDF). Washington D.C.: National Academy of Sciences.
  6. ^ Odake, Satoru (1925). "On the Occurrence of a Sulphur-containing Amino acid in Yeast". Bulletin of the Agricultural Chemical Society of Japan. 1 (8): 87–89. doi:10.1271/bbb1924.1.87. ISSN 1881-1272.