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

Abbrev Name: SAM

Synonyms: AdoMet, SAM, 2-S-adenosyl-L-methionine, S-adenosyl-methionine, adenosylmethionine, S-adenosylmethionine

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

Component of: MetJ-S-adenosylmethionine

Summary from MetaCyc:
S-adenosyl-L-methionine (AdoMet) is a sulfonium compound in which each of the carbons attached to the sulfur is activated toward nucleophilic attack.

Chemical Formula: C15H23N6O5S

Molecular Weight: 399.44 Daltons

Monoisotopic Molecular Weight: 399.14506357 Daltons

<i>S</i>-adenosyl-L-methionine compound structure

SMILES: C[S+](CC3(C(O)C(O)C(N2(C1(N=CN=C(N)C=1N=C2)))O3))CCC(C([O-])=O)[N+]

InChI: InChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/p+1/t7-,8+,10+,11+,14+,27?/m0/s1

InChIKey: InChIKey=MEFKEPWMEQBLKI-AIRLBKTGSA-O

Unification Links: CAS:29908-03-0 , ChEBI:59789 , HMDB:HMDB01185 , IAF1260:33530 , KEGG:C00019 , MetaboLights:MTBLC59789 , PubChem:24762165

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -111.889

Reactions known to consume 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+

5-(carboxymethoxy)uridine biosynthesis :
prephenate + S-adenosyl-L-methionine → 2-oxo-3-phenylpropanoate + carboxy-S-adenosyl-L-methionine + H2O

8-amino-7-oxononanoate biosynthesis I :
a malonyl-[acp] + S-adenosyl-L-methionine → a malonyl-[acp] methyl ester + S-adenosyl-L-homocysteine

autoinducer AI-2 biosynthesis I , S-adenosyl-L-methionine cycle I :
S-adenosyl-L-methionine + a demethylated methyl donor → S-adenosyl-L-homocysteine + a methylated methyl donor + 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

cyclopropane fatty acid (CFA) biosynthesis :
a [phospholipid] olefinic fatty acid + S-adenosyl-L-methionine → a [phospholipid] cyclopropane fatty acid + S-adenosyl-L-homocysteine + H+

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

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

menaquinol-8 biosynthesis :
S-adenosyl-L-methionine + demethylmenaquinol-8 → S-adenosyl-L-homocysteine + menaquinol-8 + H+

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

siroheme biosynthesis :
S-adenosyl-L-methionine + precorrin-1 → S-adenosyl-L-homocysteine + precorrin-2
S-adenosyl-L-methionine + uroporphyrinogen-III → S-adenosyl-L-homocysteine + precorrin-1 + H+

spermidine biosynthesis I :
S-adenosyl-L-methionine + H+ → CO2 + S-adenosyl 3-(methylthio)propylamine

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

ubiquinol-8 biosynthesis (prokaryotic) :
2-methoxy-6-all trans-octaprenyl-2-methoxy-1,4-benzoquinol + S-adenosyl-L-methionine → 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol + S-adenosyl-L-homocysteine + H+
3-(all-trans-octaprenyl)benzene-1,2-diol + S-adenosyl-L-methionine → 2-methoxy-6-(all-trans-octaprenyl)phenol + S-adenosyl-L-homocysteine + H+
S-adenosyl-L-methionine + 3-demethylubiquinol-8S-adenosyl-L-homocysteine + ubiquinol-8 + H+

Not in pathways:
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+
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+
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
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
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
N6-L-threonylcarbamoyladenine37 in tRNA + S-adenosyl-L-methionineN6-methyl-threonylcarbamoyladenosine 37 in tRNA + S-adenosyl-L-homocysteine + H+
rRNA + S-adenosyl-L-methionine → rRNA containing N6,N6-dimethyladenine + S-adenosyl-L-homocysteine
a [ribosomal protein L3]-L-glutamine + S-adenosyl-L-methionine → a [ribosomal protein L3]-N5-methyl-L-glutamine + S-adenosyl-L-homocysteine + H+

Reactions known to produce the compound:

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

Not in pathways:
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+
an acyl phosphate + H2O → a carboxylate + phosphate + H+
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
a 1-acyl 2-lyso-phosphatidylcholine + H2O → a carboxylate + sn-glycero-3-phosphocholine + H+

Reactions known to both consume and produce the compound:

biotin biosynthesis from 8-amino-7-oxononanoate I :
S-adenosyl-L-methionine + 8-amino-7-oxononanoate ↔ S-adenosyl-4-methylthio-2-oxobutanoate + 7,8-diaminopelargonate

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:
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+
MetJ + S-adenosyl-L-methionine = MetJ-S-adenosylmethionine
S-adenosyl-L-methionine + a protein = a methylated protein
2-ketobutyrate formate-lyase/pyruvate formate-lyase 4, inactive + a reduced flavodoxin + S-adenosyl-L-methionine = 5'-deoxyadenosine + 2-ketobutyrate formate-lyase / pyruvate formate-lyase 4 + an oxidized flavodoxin

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]

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

Inhibitor (Competitive) of: methionine adenosyltransferase [Markham80]

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

This compound has been characterized as a cofactor or prosthetic group of the following enzymes: lysine 2,3-aminomutase , HMP-P synthase

This compound has been characterized as an alternative substrate of the following enzymes: homocysteine S-methyltransferase

Regulated Transcription Units (1 total): ?

Notes:

Transcription-unit diagram


References

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

Markham80: Markham GD, Hafner EW, Tabor CW, Tabor H (1980). "S-Adenosylmethionine synthetase from Escherichia coli." J Biol Chem 1980;255(19);9082-92. PMID: 6251075


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 Tue Sep 1, 2015, BIOCYC14B.