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Escherichia coli K-12 substr. MG1655 Compound: L-methionine

Abbrev Name: met

Synonyms: M, met, methionine, L-met

Superclasses: an acid all carboxy acids a carboxylate an amino acid a non-polar amino acid
an acid all carboxy acids a carboxylate an amino acid an alpha amino acid a standard alpha amino acid
an acid all carboxy acids a carboxylate an amino acid an L-amino acid
an amino acid or its derivative an amino acid a non-polar amino acid
an amino acid or its derivative an amino acid an alpha amino acid a standard alpha amino acid
an amino acid or its derivative an amino acid an L-amino acid

Summary from MetaCyc:
L-methionine (met) is an essential amino acid and is required for a number of important cellular functions, including the initiation of protein synthesis, the methylation of DNA, rRNA and xenobiotics, and the biosynthesis of cysteine, phospholipids and polyamines.

Chemical Formula: C5H11NO2S

Molecular Weight: 149.21 Daltons

Monoisotopic Molecular Weight: 149.0510492925 Daltons

L-methionine compound structure

SMILES: CSCCC([N+])C([O-])=O

InChI: InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1

InChIKey: InChIKey=FFEARJCKVFRZRR-BYPYZUCNSA-N

Unification Links: CAS:63-68-3 , ChEBI:57844 , HMDB:HMDB00696 , IAF1260:33753 , KEGG:C00073 , MetaboLights:MTBLC57844 , PubChem:6992087

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -75.91

Reactions known to consume the compound:

S-adenosyl-L-methionine biosynthesis :
ATP + L-methionine + H2O → S-adenosyl-L-methionine + phosphate + diphosphate

tRNA charging :
initiator tRNAmet + L-methionine + ATP + H+ → an L-methionyl-[initiator tRNAmet] + AMP + diphosphate
elongator tRNAmet + L-methionine + ATP + H+ → an L-methionyl-[elongator tRNAmet] + AMP + diphosphate

Not in pathways:
L-methionine + hydrogen peroxide → L-methionine S-oxide + H2O

Reactions known to produce the compound:

4-amino-2-methyl-5-diphosphomethylpyrimidine biosynthesis :
5-amino-1-(5-phospho-β-D-ribosyl)imidazole + S-adenosyl-L-methionine → 4-amino-2-methyl-5-phosphomethylpyrimidine + 5'-deoxyadenosine + L-methionine + formate + carbon monoxide + 3 H+

biotin biosynthesis from 8-amino-7-oxononanoate I :
a sulfurated [sulfur carrier] + dethiobiotin + 2 S-adenosyl-L-methionine + 2 a reduced [2Fe-2S] ferredoxin → an unsulfurated [sulfur carrier] + biotin + 2 5'-deoxyadenosine + 2 L-methionine + 2 an oxidized [2Fe-2S] ferredoxin

heme biosynthesis II (anaerobic) :
coproporphyrinogen III + 2 S-adenosyl-L-methionine → protoporphyrinogen IX + 2 CO2 + 2 L-methionine + 2 5'-deoxyadenosine

L-methionine biosynthesis I :
L-homocysteine + N5-methyl--tetrahydropteroyl tri-L-glutamate → L-methionine + tetrahydropteroyl tri-L-glutamate
L-homocysteine + an N5-methyl-tetrahydrofolate → L-methionine + a tetrahydrofolate

lipoate biosynthesis and incorporation I , lipoate biosynthesis and incorporation II :
a [lipoyl-carrier protein] N6-octanoyl-L-lysine + 2 S-adenosyl-L-methionine + 2 a sulfurated [sulfur carrier] + 2 a reduced [2Fe-2S] ferredoxin → a [lipoyl-carrier protein] N6-lipoyl-L-lysine + 2 5'-deoxyadenosine + 2 L-methionine + 2 an unsulfurated [sulfur carrier] + 2 an oxidized [2Fe-2S] ferredoxin

N10-formyl-tetrahydrofolate biosynthesis :
L-homocysteine + an N5-methyl-tetrahydrofolate → L-methionine + a tetrahydrofolate

queuosine biosynthesis :
a 7-aminomethyl-7-deazaguanosine34 in tRNA + S-adenosyl-L-methionine → an epoxyqueuosine34 in tRNA + adenine + L-methionine + H+

S-adenosyl-L-methionine cycle I :
L-homocysteine + N5-methyl--tetrahydropteroyl tri-L-glutamate → L-methionine + tetrahydropteroyl tri-L-glutamate

thiazole biosynthesis I (E. coli) :
L-tyrosine + S-adenosyl-L-methionine + NADPH → 2-iminoacetate + 4-methylphenol + 5'-deoxyadenosine + L-methionine + NADP+ + H+

Not in pathways:
L-homocysteine + S-adenosyl-L-methionine → L-methionine + S-adenosyl-L-homocysteine + H+
glycyl-L-methionine + H2O → glycine + L-methionine
L-methionyl-L-alanine dipeptide + H2O → L-methionine + L-alanine
pyruvate formate-lyase (inactive) + a reduced flavodoxin + S-adenosyl-L-methionine → 5'-deoxyadenosine + L-methionine + pyruvate formate-lyase / 2-ketobutyrate formate-lyase + an oxidized flavodoxin
2 S-adenosyl-L-methionine + an adenine37 in tRNA + 2 a reduced [2Fe-2S] ferredoxin → S-adenosyl-L-homocysteine + L-methionine + 5'-deoxyadenosine + a 2-methyladenine37 in tRNA + 2 an oxidized [2Fe-2S] ferredoxin
2 S-adenosyl-L-methionine + adenine2503 in 23S rRNA + 2 a reduced [2Fe-2S] ferredoxin → S-adenosyl-L-homocysteine + L-methionine + 5'-deoxyadenosine + 2-methyladenine2503 in 23S rRNA + 2 an oxidized [2Fe-2S] ferredoxin
a [ribosomal protein S12] L-aspartate89 + 2 S-adenosyl-L-methionine + a sulfurated [sulfur carrier] + an reduced unknown electron acceptor → a [ribosomal protein S12] 3-methylthio-L-aspartate89 + S-adenosyl-L-homocysteine + an unsulfurated [sulfur carrier] + L-methionine + 5'-deoxyadenosine + an oxidized unknown electron acceptor + 2 H+
a peptide with an N-terminal L-methionine + H2O → L-methionine + a peptide + H+
N6-dimethylallyladenosine37 in tRNA + 2 S-adenosyl-L-methionine + a sulfurated [sulfur carrier] + an reduced unknown electron acceptor → 2-methylthio-N6-dimethylallyladenosine37 in tRNA + S-adenosyl-L-homocysteine + an unsulfurated [sulfur carrier] + 5'-deoxyadenosine + L-methionine + an oxidized unknown electron acceptor + 2 H+
L-methionine + an oxidized thioredoxin + H2O ← L-methionine-(R)-S-oxide + a reduced thioredoxin
L-methionine + an oxidized thioredoxin + H2O ← L-methionine-(S)-S-oxide + a reduced thioredoxin

Not in pathways:
a peptide with an N-terminal X-L-proline + H2O → a standard α amino acid + a peptide with an N-terminal L-proline + H+
a peptide + H2O → a standard α amino acid + a peptide
a protein + H2O → a peptide + a standard α amino acid
a protein + H2O → a peptide + a standard α amino acid

Reactions known to both consume and produce the compound:

Not in pathways:
S-adenosyl-L-methionine + an inactive ribonucleoside triphosphate reductase ↔ 5'-deoxyadenosine + an active ribonucleoside triphosphate reductase + L-methionine

In Reactions of unknown directionality:

Not in pathways:
S-methyl-L-methionine + L-homocysteine = 2 L-methionine + H+
N6-dimethylallyladenosine37 in tRNA + a sulfurated [sulfur carrier] + S-adenosyl-L-methionine + an reduced unknown electron acceptor = 2-thio-N6-dimethylallyladenosine37 in tRNA + an unsulfurated [sulfur carrier] + 5'-deoxyadenosine + L-methionine + an oxidized unknown electron acceptor + H+
L-methionine + a 2-oxo carboxylate = 2-oxo-4-methylthiobutanoate + a standard α amino acid
L-methionine + acetyl-CoA = N-α-acetyl-L-methionine + coenzyme A + H+

Not in pathways:
a 5-L-glutamyl-[peptide][periplasmic space] + an amino acid[periplasmic space] = a 5-L-glutamyl-amino acid[periplasmic space] + a peptide[periplasmic space]

Not in pathways:
a 2-acyl 1-lyso-phosphatidylcholine + H2O = a carboxylate + sn-glycero-3-phosphocholine + H+
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]

In Transport reactions:
ATP + L-methionine[periplasmic space] + H2O → ADP + L-methionine[cytosol] + phosphate + H+ ,
L-methionine[cytosol] + H+[periplasmic space]L-methionine[periplasmic space] + H+[cytosol]

Enzymes activated by L-methionine, sorted by the type of activation, are:

Activator (Mechanism unknown) of: formyltetrahydrofolate deformylase [Nagy95]

Enzymes inhibited by L-methionine, sorted by the type of inhibition, are:

Inhibitor (Allosteric) of: homoserine O-succinyltransferase [Comment 1]

Inhibitor (Mechanism unknown) of: biotin synthase [Farrar10] , L-glutamate:NADP+ oxidoreductase (transaminating) [Miller72]

Inhibitor (Other types) of: methionine synthase [Banerjee90]

This compound has been characterized as an alternative substrate of the following enzymes: leucine efflux transporter

In Growth Media: Neidhardt EZ rich defined medium , Davis and Mingioli medium A , PMA sulfur source test + met , PMA nitrogen source test + met , PMA carbon source test + met


References

Banerjee90: Banerjee RV, Frasca V, Ballou DP, Matthews RG (1990). "Participation of cob(I) alamin in the reaction catalyzed by methionine synthase from Escherichia coli: a steady-state and rapid reaction kinetic analysis." Biochemistry 1990;29(50);11101-9. PMID: 2271698

Farrar10: Farrar CE, Siu KK, Howell PL, Jarrett JT (2010). "Biotin synthase exhibits burst kinetics and multiple turnovers in the absence of inhibition by products and product-related biomolecules." Biochemistry 49(46);9985-96. PMID: 20961145

Lee66: Lee LW, Ravel JM, Shive W (1966). "Multimetabolite control of a biosynthetic pathway by sequential metabolites." J Biol Chem 1966;241(22);5479-80. PMID: 5333667

Miller72: Miller RE, Stadtman ER (1972). "Glutamate synthase from Escherichia coli. An iron-sulfide flavoprotein." J Biol Chem 247(22);7407-19. PMID: 4565085

Nagy95: Nagy PL, Marolewski A, Benkovic SJ, Zalkin H (1995). "Formyltetrahydrofolate hydrolase, a regulatory enzyme that functions to balance pools of tetrahydrofolate and one-carbon tetrahydrofolate adducts in Escherichia coli." J Bacteriol 1995;177(5);1292-8. PMID: 7868604


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by SRI International Pathway Tools version 19.0 on Thu Sep 3, 2015, biocyc13.