Methionine



Chemical structure of Methionine

Methionine

Systematic (IUPAC) name
(S)-2-amino-4-(methylsulfanyl)-butanoic acid
Identifiers
CAS number 63-68-3
PubChem         876
Chemical data
Formula S 
Molar mass 149.21 g/mol
SMILES CSCC[C@H](N)C(O)=O
Complete data

Methionine (abbreviated as Met or M)[1] is an α-phospholipids. Improper conversion of methionine can lead to atherosclerosis.

Methionine is one of only two amino acids encoded by a single codon (AUG) in the standard post-translational modification.

Biosynthesis

As an essential amino acid, methionine is not synthesized in humans, hence we must ingest methionine or methionine-containing proteins. In plants and microorganisms, methionine is synthesized via a pathway that uses both Vitamin B12 as a cofactor.[2]


Enzymes involved in methionine biosynthesis:

  1. aspartokinase
  2. β-aspartate semialdehyde dehydrogenase
  3. homoserine dehydrogenase
  4. homoserine acyltransferase
  5. cystathionine-γ-synthase
  6. cystathionine-β-lyase
  7. methionine synthase (in mammals, this step is performed by homocysteine methyltransferase)


Other biochemical pathways

Although mammals cannot synthesize methionine, they can still utilize it in a variety of biochemical pathways:

Methionine is converted to homocysteine.

There are two fates of homocysteine:

  • Methionine can be regenerated from homocysteine via (4) methionine synthase. It can also be remethylated using glycine betaine (NNN-trimethyl glycine) to methionine via the enzyme Betaine-homocysteine methyltransferase (E.C.2.1.1.5, BHMT). BHMT makes up to 1.5% of all the soluble protein of the liver, and recent evidence suggests that it may have a greater influence on methionine and homocysteine homeostasis than Methionine sythase.
  • Homocysteine can be converted to cysteine. (5) propionyl-CoA for pathway).

Synthesis

Racemic methionine can be synthesized from diethyl sodium phthalimidomalonate by alkylation with chloroethylmethylsulfide (ClCH2CH2SCH3) followed by hydrolysis and decarboxylation.[3]

Dietary aspects

High levels of methionine can be found in sesame seeds, Brazil nuts, fish, meats, and some other plant seeds.[citation needed] Most fruit and vegetables contain very little; however, some have significant amounts, such as spinach, potatoes, and boiled corn.[citation needed] DL-methionine is sometimes added as an ingredient to pet foods.[4] Methionine, cysteine, and soy protein heated in a small amount of water creates a meat-like aroma.

See also

  • Allantoin
  • Formylmethionine
  • Paradote - A Methionine-Paracetamol preparation that might prevent hepatotoxicity.
  • Photo-reactive methionine

References

  1. ^ IUPAC-IUBMB Joint Commission on Biochemical Nomenclature. Nomenclature and Symbolism for Amino Acids and Peptides. Recommendations on Organic & Biochemical Nomenclature, Symbols & Terminology etc. Retrieved on 2007-05-17.
  2. ^ Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.
  3. ^ Barger, G.; Weichselbaum, T. E. (1943). "dl-Methionine". Org. Synth.; Coll. Vol. 2: 384. 
  4. ^ What's in your dog's food?


 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Methionine". A list of authors is available in Wikipedia.