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Methionine

From an article in Wikipedia Mar 5, 2009

Methionine abbreviated as Met or M) is an α-amino acid with the chemical formula HO2CCH(NH2)CH2CH2SCH3.

This essential amino acid is classified as nonpolar.

Together with cysteine, methionine is one of two sulfur-containing proteinogenic amino acids.

Its derivative S-adenosyl methionine (SAM) serves as a methyl donor.

Methionine is an intermediate in the biosynthesis of cysteine, carnitine, taurine, lecithin, phosphatidylcholine, and other 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 genetic code (tryptophan, encoded by UGG, is the other).

The codon AUG is also the "Start" message for a ribosome that signals the initiation of protein translation from mRNA.

As a consequence, methionine is incorporated into the N-terminal position of all proteins in eukaryotes and archaea during translation, although it is usually removed by post-translational modification.

Dietary aspects

High levels of methionine can be found in sesame seeds, Brazil nuts, fish, meats, and some other plant seeds.

Most fruits and vegetables contain very little of it; however, some have significant amounts, such as spinach, potatoes, and boiled corn.

Most legumes, though high in protein, are also low in methionine.

DL-methionine is sometimes added as an ingredient to pet foods.

Methionine, cysteine, and soy protein heated in a small amount of water creates a meat-like aroma.

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 aspartic acid and cysteine.

First, aspartic acid is converted via β-aspartyl-semialdehyde into homoserine, introducing the pair of contiguous methylene groups.

Homoserine converts to O-succinyl homoserine, which then reacts with cysteine to produce cystathionine, which is cleaved to yield homocysteine.

Subsequent methylation of the thiol group by folates affords methionine.

Both cystathionine-γ-synthase and cystathionine-β-lyase require Pyridoxyl-5'-phosphate as a cofactor, whereas homocysteine methyltransferase requires Vitamin B12 as a cofactor.

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)

*

Methionine
IUPAC name	(S)-2-amino-4-(methylsulfanyl)-butanoic acid
Identifiers
Abbreviations	Met, M
CAS number	(L) 63-68-3, 59-51-8 (racemic)
PubChem	876
SMILES	CSCC[C@H](N)C(O)=O
Properties
Molecular formula	C5H11NO2S
Molar mass	149.21 g mol−1
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references

*

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Read the complaete Article in Wikipedia, Mar 5, 2009

* Methionine. (2009, February 19). In Wikipedia, The Free Encyclopedia.

Retrieved 17:30, March 5, 2009, from

http://en.wikipedia.org/w/index.php?title=

Methionine&oldid=271838928

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Read the complaete Article in Wikipedia June 18 2011

** Methionine. (2011, June 12). In Wikipedia, The Free Encyclopedia.

Retrieved 00:28, June 18, 2011, from

http://en.wikipedia.org/w/index.php?title=

Methionine&oldid=433920714

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