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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
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discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: S-adenosyl-L-methionine

Abbrev Name: SAM

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

Superclasses: an amino acid or its derivative an amino acid an alpha amino acid a non-standard alpha amino acid

Summary:
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

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:44229224

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 124.03472 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

(S)-reticuline biosynthesis I :
(S)-coclaurine + S-adenosyl-L-methionine → (S)-N-methylcoclaurine + S-adenosyl-L-homocysteine + H+
3'-hydroxy-N-methyl-(S)-coclaurine + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + (S)-reticuline + H+
(S)-norcoclaurine + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + (S)-coclaurine + H+

(S)-reticuline biosynthesis II :
S-norlaudanosoline + 3 S-adenosyl-L-methionine → (S)-reticuline + 3 S-adenosyl-L-homocysteine + 3 H+

1,3,5-trimethoxybenzene biosynthesis :
3,5-dimethoxyphenol + S-adenosyl-L-methionine → 1,3,5-trimethoxybenzene + S-adenosyl-L-homocysteine + H+
3,5-dihydroxyanisole + S-adenosyl-L-methionine → 3,5-dimethoxyphenol + S-adenosyl-L-homocysteine + H+
phloroglucinol + S-adenosyl-L-methionine → 3,5-dihydroxyanisole + S-adenosyl-L-homocysteine + H+

1,4-dihydroxy-6-naphthoate biosynthesis I :
3-[(1-carboxyvinyl)oxy]benzoate + S-adenosyl-L-methionine + H2O → 6-amino-6-deoxyfutalosine + L-methionine + hydrogen carbonate + H+
dehypoxanthine futalosine + S-adenosyl-L-methionine → cyclic dehypoxanthine futalosine + L-methionine + 5'-deoxyadenosyl radical + 2 H+

1,4-dihydroxy-6-naphthoate biosynthesis II :
3-[(1-carboxyvinyl)oxy]benzoate + S-adenosyl-L-methionine + H2O → 6-amino-6-deoxyfutalosine + L-methionine + hydrogen carbonate + H+
dehypoxanthine futalosine + S-adenosyl-L-methionine → cyclic dehypoxanthine futalosine + L-methionine + 5'-deoxyadenosyl radical + 2 H+

2'-deoxymugineic acid phytosiderophore biosynthesis , nicotianamine biosynthesis :
3 S-adenosyl-L-methionine → nicotianamine + 3 S-methyl-5'-thioadenosine + 3 H+

2-methylisoborneol biosynthesis :
S-adenosyl-L-methionine + geranyl diphosphate → S-adenosyl-L-homocysteine + (E)-2-methylgeranyl diphosphate + H+

26,27-dehydrozymosterol metabolism :
26,27-dehydrozymosterol + methanol + S-adenosyl-L-methionine + H+ → 24-alkyl sterol 3 + S-adenosyl-L-homocysteine + methyl-group
26,27-dehydrozymosterol + methanol + S-adenosyl-L-methionine + H+ → 24-alkyl sterol 2 + S-adenosyl-L-homocysteine + methyl-group
26,27-dehydrozymosterol + S-adenosyl-L-methionine → 24-alkyl sterol 1 + S-adenosyl-L-homocysteine

3,5-dimethoxytoluene biosynthesis :
orcinol + S-adenosyl-L-methionine → 3-methoxy-5-hydroxytoluene + S-adenosyl-L-homocysteine + H+
3-methoxy-5-hydroxytoluene + S-adenosyl-L-methionine → 3,5-dimethoxytoluene + S-adenosyl-L-homocysteine + H+

3-methylarginine biosynthesis :
2-ketoarginine + S-adenosyl-L-methionine → 5-guanidino-3-methyl-2-oxo-pentanoate + S-adenosyl-L-homocysteine + H+

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

6-gingerol biosynthesis :
1-(3,4-dihydroxyphenyl)-5-hydroxy-3-decanone + S-adenosyl-L-methionine → 6-gingerol + S-adenosyl-L-homocysteine + H+

6-methoxymellein biosynthesis :
6-hydroxymellein + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + 6-methoxymellein + H+

7-(3-amino-3-carboxypropyl)-wyosine biosynthesis :
N1-methylguanine37 in tRNAPhe + pyruvate + S-adenosyl-L-methionine → 4-demethylwyosine37 in tRNAPhe + L-methionine + 5'-deoxyadenosine + CO2 + H2O
S-adenosyl-L-methionine + 7-[(3S)-3-amino-3-carboxypropyl]-4-demethylwyosine37 in tRNAPheS-adenosyl-L-homocysteine + 7-[(3S)-(3-amino-3-carboxypropyl)]-wyosine37 in tRNAPhe + H+
S-adenosyl-L-methionine + 4-demethylwyosine37 in tRNAPheS-methyl-5'-thioadenosine + 7-[(3S)-3-amino-3-carboxypropyl]-4-demethylwyosine37 in tRNAPhe + H+
guanine37 in tRNAPhe + S-adenosyl-L-methionineN1-methylguanine37 in tRNAPhe + S-adenosyl-L-homocysteine + H+

7-dehydroporiferasterol biosynthesis :
S-adenosyl-L-methionine + cycloartenol → S-adenosyl-L-homocysteine + 24-methylenecycloartanol + H+

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

acacetin biosynthesis :
apigenin + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + acacetin + H+

aclacinomycin biosynthesis :
S-adenosyl-L-methionine + aklanonate → S-adenosyl-L-homocysteine + methyl aklanonate

acridone alkaloid biosynthesis , N-methylanthraniloyl-β-D-glucopyranose biosynthesis , superpathway avenacin A biosynthesis :
anthranilate + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + N-methylanthranilate + H+

aflatoxins B1 and G1 biosynthesis :
sterigmatocystin + S-adenosyl-L-methionine → 8-O-methylsterigmatocystin + S-adenosyl-L-homocysteine + H+

aflatoxins B2 and G2 biosynthesis :
dihydrosterigmatocystin + S-adenosyl-L-methionine → 8-O-methyldihydrosterigmatocystin + S-adenosyl-L-homocysteine + H+
dihydrodemethylsterigmatocystin + S-adenosyl-L-methionine → dihydrosterigmatocystin + S-adenosyl-L-homocysteine + H+

ajmaline and sarpagine biosynthesis :
17-O-acetylnorajmaline + S-adenosyl-L-methionine → 17-O-acetylajmaline + S-adenosyl-L-homocysteine
norajmaline + S-adenosyl-L-methionine → ajmaline + S-adenosyl-L-homocysteine + H+

arsenate detoxification I (glutaredoxin) :
S-adenosyl-L-methionine + methylarsonite → S-adenosyl-L-homocysteine + cacodylate + 2 H+
arsenite + S-adenosyl-L-methionine → methylarsonate + S-adenosyl-L-homocysteine + H+

autoinducer AI-1 biosynthesis :
an acyl-[acyl-carrier protein] + S-adenosyl-L-methionine → a holo-[acyl-carrier protein] + S-methyl-5'-thioadenosine + an N-acyl-L-homoserine lactone + H+

autoinducer AI-2 biosynthesis I , autoinducer AI-2 biosynthesis II (Vibrio) , methionine degradation I (to homocysteine) , S-adenosyl-L-methionine cycle I , S-adenosyl-L-methionine cycle II :
S-adenosyl-L-methionine + a demethylated methyl acceptor → S-adenosyl-L-homocysteine + a methylated methyl acceptor + H+

berberine biosynthesis :
(S)-scoulerine + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + S-tetrahydrocolumbamine + H+

β-alanine betaine biosynthesis :
N,N-dimethyl-β-alanine + S-adenosyl-L-methionine → β-alanine betaine + S-adenosyl-L-homocysteine + H+
N-methyl-β-alanine + S-adenosyl-L-methionine → N,N-dimethyl-β-alanine + S-adenosyl-L-homocysteine + H+
β-alanine + S-adenosyl-L-methionine → N-methyl-β-alanine + S-adenosyl-L-homocysteine + H+

betaxanthin biosynthesis :
S-adenosyl-L-methionine + dopamine → S-adenosyl-L-homocysteine + 3-methoxytyramine + H+

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

bixin biosynthesis :
bixin + S-adenosyl-L-methionine → bixin dimethyl ester + S-adenosyl-L-homocysteine
norbixin + S-adenosyl-L-methionine → bixin + S-adenosyl-L-homocysteine

botryococcenes and methylated squalene biosynthesis :
showacene + S-adenosyl-L-methionine → 3,20-dimethyl-1,2,21,22-tetradehydro-2,3,20,21-tetrahydrobotryococcene + S-adenosyl-L-homocysteine + H+
C30 botryococcene + S-adenosyl-L-methionine → showacene + S-adenosyl-L-homocysteine + H+
3-methyl-1,2-didehydro-2,3-dihydrosqualene + S-adenosyl-L-methionine → 3,22-dimethyl-1,2,23,24-tetradehydro-2,3,22,23-tetrahydrosqualene + S-adenosyl-L-homocysteine + H+
squalene + S-adenosyl-L-methionine → 3-methyl-1,2-didehydro-2,3-dihydrosqualene + S-adenosyl-L-homocysteine + H+
3,20-dimethyl-1,2,21,22-tetradehydro-2,3,20,21-tetrahydrobotryococcene + S-adenosyl-L-methionine → C33 botryococcene + S-adenosyl-L-homocysteine + H+
C33 botryococcene + S-adenosyl-L-methionine → a C34 botryococcenes + S-adenosyl-L-homocysteine + H+

brassicicene C biosynthesis :
fusicocca-1,10(14)-diene-3,8β,16-triol + S-adenosyl-L-methionine → fusicocca-1,10(14)-diene-16-(hydroxymethyl)-3,8β-diol + S-adenosyl-L-homocysteine + H+

caffeine biosynthesis I :
theobromine + S-adenosyl-L-methionine → caffeine + S-adenosyl-L-homocysteine + H+
7-methylxanthine + S-adenosyl-L-methionine → theobromine + S-adenosyl-L-homocysteine + H+
xanthosine + S-adenosyl-L-methionine → 7-methylxanthosine + S-adenosyl-L-homocysteine + H+

caffeine biosynthesis II (via paraxanthine) :
paraxanthine + S-adenosyl-L-methionine → caffeine + S-adenosyl-L-homocysteine + H+
7-methylxanthine + S-adenosyl-L-methionine → paraxanthine + S-adenosyl-L-homocysteine + H+
xanthosine + S-adenosyl-L-methionine → 7-methylxanthosine + S-adenosyl-L-homocysteine + H+

capsaicin biosynthesis , chlorogenic acid biosynthesis I , coumarins biosynthesis (engineered) , scopoletin biosynthesis :
caffeoyl-CoA + S-adenosyl-L-methionine → feruloyl-CoA + S-adenosyl-L-homocysteine + H+

catecholamine biosynthesis :
S-adenosyl-L-methionine + (R)-noradrenaline → S-adenosyl-L-homocysteine + (R)-adrenaline + H+

cephamycin C biosynthesis :
7-α-hydroxy-O-carbamoyl-deacetylcephalosporin C + S-adenosyl-L-methionine → cephamycin C + S-adenosyl-L-homocysteine + H+

chanoclavine I aldehyde biosynthesis :
4-(3-methylbut-2-enyl)-L-tryptophan + S-adenosyl-L-methionine → 4-(3-methylbut-2-enyl)-L-abrine + S-adenosyl-L-homocysteine + H+

chlorophyllide a biosynthesis I (aerobic, light-dependent) , chlorophyllide a biosynthesis II (anaerobic) , chlorophyllide a biosynthesis III (aerobic, light independent) :
Mg-protoporphyrin + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + magnesium-protoporphyrin IX 13-monomethyl ester

choline biosynthesis I :
N-dimethylethanolamine phosphate + S-adenosyl-L-methionine → phosphocholine + S-adenosyl-L-homocysteine + H+
N-methylethanolamine phosphate + S-adenosyl-L-methionine → N-dimethylethanolamine phosphate + S-adenosyl-L-homocysteine + H+
phosphoryl-ethanolamine + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + N-methylethanolamine phosphate + H+

choline biosynthesis II :
N-dimethylethanolamine + S-adenosyl-L-methionine → choline + S-adenosyl-L-homocysteine + H+
N-monomethylethanolamine + S-adenosyl-L-methionineN-dimethylethanolamine + S-adenosyl-L-homocysteine + H+
ethanolamine + S-adenosyl-L-methionineN-monomethylethanolamine + S-adenosyl-L-homocysteine + H+

chrysoeriol biosynthesis :
luteolin + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + chrysoeriol + H+

cob(II)yrinate a,c-diamide biosynthesis I (early cobalt insertion) :
S-adenosyl-L-methionine + cobalt-precorrin-4 → S-adenosyl-L-homocysteine + cobalt-precorrin-5A + H+
cobalt-precorrin-7 + S-adenosyl-L-methionine → cobalt-precorrin-8 + S-adenosyl-L-homocysteine
cobalt-precorrin-3 + S-adenosyl-L-methionine → cobalt-precorrin-4 + S-adenosyl-L-homocysteine
cobalt-precorrin-5B + S-adenosyl-L-methionine → cobalt-precorrin-6A + S-adenosyl-L-homocysteine
cobalt-precorrin-6B + S-adenosyl-L-methionine + H+ → cobalt-precorrin-7 + S-adenosyl-L-homocysteine + CO2
S-adenosyl-L-methionine + uroporphyrinogen-III → S-adenosyl-L-homocysteine + precorrin-1 + H+
S-adenosyl-L-methionine + precorrin-1 → S-adenosyl-L-homocysteine + precorrin-2
S-adenosyl-L-methionine + cobalt-sirohydrochlorin → S-adenosyl-L-homocysteine + cobalt-factor III + H+

cob(II)yrinate a,c-diamide biosynthesis II (late cobalt incorporation) :
precorrin-6B + S-adenosyl-L-methionine + H+ → precorrin-7 + S-adenosyl-L-homocysteine + CO2
precorrin-4 + S-adenosyl-L-methionine → precorrin-5 + S-adenosyl-L-homocysteine + H+
precorrin-7 + S-adenosyl-L-methionine → precorrin-8x + S-adenosyl-L-homocysteine + 2 H+
S-adenosyl-L-methionine + uroporphyrinogen-III → S-adenosyl-L-homocysteine + precorrin-1 + H+
S-adenosyl-L-methionine + precorrin-1 → S-adenosyl-L-homocysteine + precorrin-2
precorrin-5 + S-adenosyl-L-methionine + H2O → precorrin-6A + S-adenosyl-L-homocysteine + acetate + 2 H+
precorrin-2 + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + precorrin-3A + H+
precorrin-3B + S-adenosyl-L-methionine → precorrin-4 + S-adenosyl-L-homocysteine + 2 H+

colchicine biosynthesis :
(S)-isoandrocymbine + S-adenosyl-L-methionine → O-methylandrocymbine + S-adenosyl-L-homocysteine + H+

creatine biosynthesis :
guanidinoacetate + S-adenosyl-L-methionineS-adenosyl-L-homocysteine + creatine + H+

cyclopropane and cyclopropene fatty acid biosynthesis :
oleate + S-adenosyl-L-methionine → dihydrosterculate + S-adenosyl-L-homocysteine + H+

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

daphnetin modification :
S-adenosyl-L-methionine + daphnetin → S-adenosyl-L-homocysteine + 7-hydroxy-8-methoxycoumarin + H+

daunorubicin biosynthesis :
S-adenosyl-L-methionine + aklanonate → S-adenosyl-L-homocysteine + methyl aklanonate
13-deoxycarminomycin + S-adenosyl-L-methionine → 13-deoxydaunorubicin + S-adenosyl-L-homocysteine + H+

dehydrophos biosynthesis :
desmethyl dehydrophos + S-adenosyl-L-methionine → dehydrophos + S-adenosyl-L-homocysteine

diacylglyceryl-N,N,N-trimethylhomoserine biosynthesis :
S-adenosyl-L-methionine + a 1,2-diacyl-sn-glycerol → a diacylglycerolhomoserine + S-methyl-5'-thioadenosine + H+
a diacylglycerolhomoserine + 3 S-adenosyl-L-methionine → a diacylglyceryl-N,N,N-trimethylhomoserine + 3 S-adenosyl-L-homocysteine + 3 H+

DIMBOA-glucoside biosynthesis :
TRIBOA-β-D-glucoside + S-adenosyl-L-methionine → DIMBOA-β-D-glucoside + S-adenosyl-L-homocysteine + H+

Reactions known to produce the compound:

2'-deoxymugineic acid phytosiderophore biosynthesis , ethylene biosynthesis I (plants) , methionine degradation I (to homocysteine) , S-adenosyl-L-methionine biosynthesis , S-adenosyl-L-methionine cycle II :
ATP + L-methionine + H2O → S-adenosyl-L-methionine + phosphate + diphosphate

Not in pathways:
amino acids(n) + H2O → amino acids(n-1) + an α amino acid
an α amino acid ester + H2O → an alcohol + an α amino acid + H+
a protein + H2O → a protein + an α amino acid

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

salinosporamide A biosynthesis :
S-adenosyl-L-methionine + chloride ↔ 5'-deoxy-5'-chloroadenosine + L-methionine

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

In Reactions of unknown directionality:

Not in pathways:
mercaptohistidine + S-adenosyl-L-methionine = ovothiol + S-adenosyl-L-homocysteine + H+
S-adenosyl-L-methionine + a uracil2634 in 25S rRNA = S-adenosyl-L-homocysteine + N3-methyluracil2634 in 25S rRNA + H+
S-adenosyl-L-methionine + a uracil2843 in 25S rRNA = S-adenosyl-L-homocysteine + N3-methyluracil2843 in 25S rRNA + H+
S-adenosyl-L-methionine + cytosine2278 in 25S rRNA = S-adenosyl-L-homocysteine + 5-methylcytosine2278 in 25S rRNA + H+
S-adenosyl-L-methionine + cytosine2870 in 25S rRNA = S-adenosyl-L-homocysteine + 5-methylcytosine2870 in 25S rRNA + H+
S-adenosyl-L-methionine + a guanine1575 in 18S tRNA = S-adenosyl-L-homocysteine + N7-methylguanine1575 in 18S rRNA
N6-dimethylallyladenosine37 in tRNA + S-adenosyl-L-methionine + a sulfurated [sulfur carrier] = 2-thio-N6-dimethylallyladenosine37 in tRNA + an unsulfurated [sulfur carrier] + L-methionine + 5'-deoxyadenosine
a CpG site + S-adenosyl-L-methionine = a 5-methyl-CpG site + S-adenosyl-L-homocysteine + H+
4-coumaryl-CoA + S-adenosyl-L-methionine = S-methyl-5'-thioadenosine + N-4-coumaryl-L-homoserine lactone + coenzyme A + H+
isovaleryl-CoA + S-adenosyl-L-methionine = S-methyl-5'-thioadenosine + N-isovaleryl-L-homoserine lactone + coenzyme A + H+
S-adenosyl-L-methionine = L-homoserine lactone + S-methyl-5'-thioadenosine
a (R)-3-hydroxybutanoyl-[acp] + S-adenosyl-L-methionine = a holo-[acyl-carrier protein] + S-methyl-5'-thioadenosine + HAI-1 + H+
an octanoyl-[acp] + S-adenosyl-L-methionine = a holo-[acyl-carrier protein] + S-methyl-5'-thioadenosine + VAI-2 + H+
a butyryl-[acp] + S-adenosyl-L-methionine = a holo-[acyl-carrier protein] + S-methyl-5'-thioadenosine + PAI-2 + H+
a 3-oxo-dodecanoyl-[acp] + S-adenosyl-L-methionine = a holo-[acyl-carrier protein] + S-methyl-5'-thioadenosine + PAI-1 + H+
a 3-oxo-hexanoyl-[acp] + S-adenosyl-L-methionine = a holo-[acyl-carrier protein] + S-methyl-5'-thioadenosine + VAI-1 + H+
a 3-oxo-octanoyl-[acp] + S-adenosyl-L-methionine = a holo-[acyl-carrier protein] + S-methyl-5'-thioadenosine + AAI + H+
a uridine in tRNA + S-adenosyl-L-methionine = a tRNA 3-(3-amino-3-carboxypropyl)-uridine + S-methyl-5'-thioadenosine + H+
S-adenosyl-L-methionine + a protein = a methylated protein
nocardicin E + S-adenosyl-L-methionine = isonocardicin A + S-methyl-5'-thioadenosine + H+
a [formate C acetyltransferase]-glycine + S-adenosyl-L-methionine + a reduced flavodoxin = a [formate C acetyltransferase]-glycin -2-yl radical + 5'-deoxyadenosine + L-methionine + a flavodoxin semiquinone
N6-dimethylallyladenine + S-adenosyl-L-methionine = discadenine + S-methyl-5'-thioadenosine + H+
S-adenosyl-L-methionine + H2O = L-homoserine + S-methyl-5'-thioadenosine + H+


a 5-L-glutamyl-[peptide] + an amino acid = a 5-L-glutamyl-amino acid + a peptide

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

Activator (Mechanism unknown) of: methionine adenosyltransferase [Comment 1]

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

Inhibitor (Competitive) of: methionine adenosyltransferase [Markham80]

Inhibitor (Noncompetitive) of: homoserine O-acetyltransferase [Shiio81]

Inhibitor (Allosteric) of: homoserine O-succinyltransferase [Comment 2]

Inhibitor (Mechanism unknown) of: S-methyl-L-methionine decarboxylase [Kocsis00] , methionine adenosyltransferase [Comment 3] , O-acetylhomoserine sulfhydrylase [Belfaiza98] , homoserine O-acetyltransferase [Yamagata87a] , methionine adenosyltransferase [Cabrero87] , S-adenosylmethionine synthetase [Schroder97]

This compound has been characterized as a cofactor or prosthetic group of the following enzymes: HMP-P synthase , lysine 2,3-aminomutase , 15-demethoxy-ε-rhodomycinone 10-hydroxylase , 15-demethoxyaclacinomycin T decarboxylase , 15-demethoxyaclacinomycin A decarboxylase , (2R,3R)-3-methylornithine synthase , nicotine N-methyltransferase , 2-hydroxyethylphosphonate methylase , lysine 2,3-aminomutase


References

Belfaiza98: Belfaiza J, Martel A, Margarita D, Saint Girons I (1998). "Direct sulfhydrylation for methionine biosynthesis in Leptospira meyeri." J Bacteriol 180(2);250-5. PMID: 9440513

Cabrero87: Cabrero C, Puerta J, Alemany S (1987). "Purification and comparison of two forms of S-adenosyl-L-methionine synthetase from rat liver." Eur J Biochem 170(1-2);299-304. PMID: 3121322

Chou72: Chou TC, Talalay P (1972). "The mechanism of S-adenosyl-L-methionine synthesis by purified preparations of bakers' yeast." Biochemistry 1972;11(6);1065-73. PMID: 4552214

Kocsis00: Kocsis MG, Hanson AD (2000). "Biochemical evidence for two novel enzymes in the biosynthesis of 3-dimethylsulfoniopropionate in Spartina alterniflora." Plant Physiol 123(3);1153-61. PMID: 10889264

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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