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

Abbrev Name: SAH

Synonyms: S-adenosylhomocysteine, 2-S-adenosyl-L-homocysteine, AdoHcy, 2-S-adenosyl-L-homocysteine, S-adenosyl-homocysteine, S-adenosylhomocysteine, adenosyl-homo-cys, adenosylhomocysteine, adenosylhomo-cys, SAH

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

Chemical Formula: C14H20N6O5S

Molecular Weight: 384.41 Daltons

Monoisotopic Molecular Weight: 384.1215884737 Daltons

SMILES: C(SCC3(C(O)C(O)C(N2(C1(N=CN=C(N)C=1N=C2)))O3))CC(C([O-])=O)[N+]

InChI: InChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1

InChIKey: InChIKey=ZJUKTBDSGOFHSH-WFMPWKQPSA-N

Unification Links: CAS:979-92-0 , ChEBI:57856 , HMDB:HMDB00939 , IAF1260:33543 , KEGG:C00021 , MetaboLights:MTBLC57856 , PubChem:50986259

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -121.369

Reactions known to consume the compound:

autoinducer AI-2 biosynthesis I , S-adenosyl-L-methionine cycle I :
S-adenosyl-L-homocysteine + H2O ← S-ribosyl-L-homocysteine + adenine

Reactions known to produce the compound:

5-(carboxymethoxy)uridine biosynthesis :
a 5-hydroxyuridine34 in tRNA + carboxy-S-adenosyl-L-methionine → a 5-(carboxymethoxy)uridine34 in tRNA + S-adenosyl-L-homocysteine + H+

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 acceptor → S-adenosyl-L-homocysteine + a methylated methyl acceptor + 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+

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

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:
a [protein]-α-L-glutamate + S-adenosyl-L-methionine → a [protein]-L-glutamate-O5-methyl-ester + S-adenosyl-L-homocysteine
S-adenosyl-L-methionine + TargluS-adenosyl-L-homocysteine + Targlu-Me
S-adenosyl-L-methionine + TsrgluS-adenosyl-L-homocysteine + Tsrglu-Me
S-adenosyl-L-methionine + TrggluS-adenosyl-L-homocysteine + Trgglu-Me
S-adenosyl-L-methionine + TapgluS-adenosyl-L-homocysteine + Tapglu-Me
L-homocysteine + S-adenosyl-L-methionine → L-methionine + S-adenosyl-L-homocysteine + H+
trans-aconitate + S-adenosyl-L-methionine → (E)-3-(methoxycarbonyl)pent-2-enedioate + S-adenosyl-L-homocysteine
rRNA + S-adenosyl-L-methionine → rRNA containing N6,N6-dimethyladenine + S-adenosyl-L-homocysteine
a non-methylated ribosomal protein L11 + S-adenosyl-L-methionine → a methylated ribosomal protein L11 + S-adenosyl-L-homocysteine
S-adenosyl-L-methionine + guanine527 in 16S rRNA → S-adenosyl-L-homocysteine + N7-methylguanine527 in 16S rRNA
an rRNA + S-adenosyl-L-methionine → rRNA containing 2-methyladenine + S-adenosyl-L-homocysteine
tellurite + S-adenosyl-L-methionine → methanetelluronate + S-adenosyl-L-homocysteine
guanine46 in tRNA + S-adenosyl-L-methionine → N7-methylguanine46 in tRNA + S-adenosyl-L-homocysteine
a DNA adenine + S-adenosyl-L-methionine → S-adenosyl-L-homocysteine + a DNA 6-methylaminopurine + H+
guanine2069 in 23S rRNA + S-adenosyl-L-methionine → N7-methylguanine2069 in 23S rRNA + S-adenosyl-L-homocysteine
2 S-adenosyl-L-methionine + adenine2503 in 23S rRNA → S-adenosyl-L-homocysteine + L-methionine + 5'-deoxyadenosine + 2-methyladenine2503 in 23S rRNA
a uracil54 in tRNA + S-adenosyl-L-methionine → a 5-methyluracil54 in tRNA + S-adenosyl-L-homocysteine + H+
a guanine1516 in 16S rRNA + S-adenosyl-L-methionine → an N2-methylguanine1516 in 16S rRNA + S-adenosyl-L-homocysteine + H+
S-adenosyl-L-methionine + guanine966 in 16S rRNA → S-adenosyl-L-homocysteine + N2-methylguanine966 in 16S rRNA + H+
S-adenosyl-L-methionine + adenine37 in tRNA1valS-adenosyl-L-homocysteine + N6-methyladenine37 in tRNA1val + H+
guanine37 in tRNA + S-adenosyl-L-methionine → N1-methylguanine37 in tRNA + S-adenosyl-L-homocysteine + H+
a uridine32 in tRNA + S-adenosyl-L-methionine → a 2'-O-methyluridine32 in tRNA + S-adenosyl-L-homocysteine + H+
a cytidine 32 in tRNA + S-adenosyl-L-methionine → a 2'-O-methylcytidine32 in tRNA + S-adenosyl-L-homocysteine + H+
a 5-carboxymethylaminomethyluridine34 in tRNALeu + S-adenosyl-L-methionine → a 5-carboxymethylaminomethyl-2'-O-methyluridine34 in tRNALeu + S-adenosyl-L-homocysteine + H+
a cytidine34 in tRNA + S-adenosyl-L-methionine → a 2'-O-methylcytidine34 in tRNA + S-adenosyl-L-homocysteine + H+
uridine2552 in 23S rRNA + S-adenosyl-L-methionine → 2-O-methyluridine2552 in 23S rRNA + S-adenosyl-L-homocysteine + H+
S-adenosyl-L-methionine + cytidine1402 in 16S rRNA → S-adenosyl-L-homocysteine + N4-methylcytidine1402 in 16S rRNA + H+
S-adenosyl-L-methionine + cytidine1402 in 16S rRNA → S-adenosyl-L-homocysteine + 2'-O-methylcytidine1402 in 16S rRNA + H+
S-adenosyl-L-methionine + guanine1835 in 23S rRNA → S-adenosyl-L-homocysteine + N2-methylguanine1835 in 23S rRNA + H+
cytosine1962 in 23S rRNA + S-adenosyl-L-methionine → 5-methylcytosine1962 in 23S rRNA + S-adenosyl-L-homocysteine + H+
a uracil1939 in 23S rRNA + S-adenosyl-L-methionine → a 5-methyluracil1939 in 23S rRNA + S-adenosyl-L-homocysteine + H+
a uracil747 in 23S rRNA + S-adenosyl-L-methionine → a 5-methyluracil747 in 23S rRNA + S-adenosyl-L-homocysteine + H+
S-adenosyl-L-methionine + uracil1498 in 16S rRNA → S-adenosyl-L-homocysteine + N3-methyluracil1498 in 16S rRNA + H+
S-adenosyl-L-methionine + cytosine1407 in 16S rRNA → S-adenosyl-L-homocysteine + 5-methylcytosine1407 in 16S rRNA + H+
S-adenosyl-L-methionine + a pseudouridine1915 in 23S rRNA → S-adenosyl-L-homocysteine + an N3-methylpseudouridine1915 in 23S rRNA + H+
cytosine967 in 16S rRNA + S-adenosyl-L-methionine → 5-methylcytosine967 in 16S rRNA + S-adenosyl-L-homocysteine + H+
cytidine2498 in 23S rRNA + S-adenosyl-L-methionine → 2-O-methylcytidine2498 in 23S rRNA + S-adenosyl-L-homocysteine + H+
guanosine2251 in 23S rRNA + S-adenosyl-L-methionine → 2-O-methylguanosine2251 in 23S rRNA + S-adenosyl-L-homocysteine + H+
S-adenosyl-L-methionine + guanine1207 in 16S rRNA → S-adenosyl-L-homocysteine + N2-methylguanine1207 in 16S rRNA + H+
S-adenosyl-L-methionine + guanine2445 in 23S rRNA → S-adenosyl-L-homocysteine + N2-methylguanine2445 in 23S rRNA + H+
guanine745 in 23S rRNA + S-adenosyl-L-methionine → N1-methylguanine745 in 23S rRNA + S-adenosyl-L-homocysteine + H+
a guanosine18 in tRNA + S-adenosyl-L-methionine → a 2'-O-methylguanosine18 in tRNA + S-adenosyl-L-homocysteine + H+
2 S-adenosyl-L-methionine + an adenine37 in tRNA → S-adenosyl-L-homocysteine + L-methionine + 5'-deoxyadenosine + a 2-methyladenine37 in tRNA
adenine2030 in 23S rRNA + S-adenosyl-L-methionine → N6-methyladenine2030 in 23S rRNA + S-adenosyl-L-homocysteine + H+
a cytosine in DNA + S-adenosyl-L-methionine → a DNA 5-methylcytosine + S-adenosyl-L-homocysteine + H+
N6-dimethylallyladenosine37 in tRNA + 2 S-adenosyl-L-methionine + a sulfurated [sulfur carrier] → 2-methylthio-N6-dimethylallyladenosine37 in tRNA + S-adenosyl-L-homocysteine + L-methionine + 5'-deoxyadenosine + an unsulfurated [sulfur carrier] + H+
S-adenosyl-L-methionine + a [protein]-L-β-isoaspartate → S-adenosyl-L-homocysteine + a protein L-β-isoaspartate α-methyl ester
2-thio-N6-dimethylallyladenosine37 in tRNA + S-adenosyl-L-methionine → 2-methylthio-N6-dimethylallyladenosine37 in tRNA + S-adenosyl-L-homocysteine + H+
a [ribosomal protein S12] L-aspartate89 + 2 S-adenosyl-L-methionine + a sulfurated [sulfur carrier] → a [ribosomal protein S12] 3-methylthio-L-aspartate89 + S-adenosyl-L-homocysteine + an unsulfurated [sulfur carrier] + L-methionine + 5'-deoxyadenosine + H+
a tRNA containing 5-aminomethyl-2-thiouridine + S-adenosyl-L-methionine → S-adenosyl-L-homocysteine + a 5-methylaminomethyl-2-thiouridine in tRNA + 2 H+
adenine1518/adenine1519 in 16S rRNA + 4 S-adenosyl-L-methionine → N6-dimethyladenine1518/N6-dimethyladenine1519in 16S rRNA + 4 S-adenosyl-L-homocysteine + 4 H+
adenine1618 in 23S rRNA + S-adenosyl-L-methionine → N6-methyladenine1618 in 23S rRNA + S-adenosyl-L-homocysteine + H+
a [release factor]-L-glutamine + S-adenosyl-L-methionine → a [release factor]-N5-methyl-L-glutamine + S-adenosyl-L-homocysteine + H+
a [ribosomal protein L3]-L-glutamine + S-adenosyl-L-methionine → a [ribosomal protein L3]-N5-methyl-L-glutamine + S-adenosyl-L-homocysteine + H+
N6-L-threonylcarbamoyladenine37 in tRNA + S-adenosyl-L-methionine → N6-methyl-threonylcarbamoyladenosine 37 in tRNA + S-adenosyl-L-homocysteine + H+

In Reactions of unknown directionality:

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]

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

Inhibitor (Competitive) of: S-adenosylmethionine:tRNA ribosyltransferase-isomerase [Van03] , chemotaxis protein methyltransferase [Neidhardt96] , pyruvate formate-lyase activating enzyme [Knappe90, Comment 1] , cyclopropane fatty acyl phospholipid synthase [Grogan97, Taylor79, Guerard04] , DNA-cytosine methyltransferase [Crooks84] , tRNA m1G37 methyltransferase [Hjalmarsson83, Lahoud11]

Inhibitor (Mechanism unknown) of: biotin synthase [Farrar10] , 5'-methylthioadenosine nucleosidase [Cornell98] , trans-aconitate 2-methyltransferase [Cai99] , ribonucleoside-triphosphate reductase [Eliasson92]


References

Cai99: Cai H, Clarke S (1999). "A novel methyltransferase catalyzes the methyl esterification of trans-aconitate in Escherichia coli." J Biol Chem 274(19);13470-9. PMID: 10224113

Cornell98: Cornell KA, Riscoe MK (1998). "Cloning and expression of Escherichia coli 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase: identification of the pfs gene product." Biochim Biophys Acta 1396(1);8-14. PMID: 9524204

Crooks84: Crooks PA, Tribe MJ, Pinney RJ (1984). "Inhibition of bacterial DNA cytosine-5-methyltransferase by S-adenosyl-L-homocysteine and some related compounds." J Pharm Pharmacol 36(2);85-9. PMID: 6143811

Eliasson92: Eliasson R, Pontis E, Fontecave M, Gerez C, Harder J, Jornvall H, Krook M, Reichard P (1992). "Characterization of components of the anaerobic ribonucleotide reductase system from Escherichia coli." J Biol Chem 267(35);25541-7. PMID: 1460049

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

Grogan97: Grogan DW, Cronan JE (1997). "Cyclopropane ring formation in membrane lipids of bacteria." Microbiol Mol Biol Rev 1997;61(4);429-41. PMID: 9409147

Guerard04: Guerard C, Breard M, Courtois F, Drujon T, Ploux O (2004). "Synthesis and evaluation of analogues of S-adenosyl-L-methionine, as inhibitors of the E. coli cyclopropane fatty acid synthase." Bioorg Med Chem Lett 14(7);1661-4. PMID: 15026045

Hjalmarsson83: Hjalmarsson KJ, Bystrom AS, Bjork GR (1983). "Purification and characterization of transfer RNA (guanine-1)methyltransferase from Escherichia coli." J Biol Chem 258(2);1343-51. PMID: 6337136

Knappe90: Knappe J, Sawers G (1990). "A radical-chemical route to acetyl-CoA: the anaerobically induced pyruvate formate-lyase system of Escherichia coli." FEMS Microbiol Rev 1990;6(4);383-98. PMID: 2248795

Lahoud11: Lahoud G, Goto-Ito S, Yoshida K, Ito T, Yokoyama S, Hou YM (2011). "Differentiating analogous tRNA methyltransferases by fragments of the methyl donor." RNA 17(7);1236-46. PMID: 21602303

Neidhardt96: Neidhardt FC, Curtiss III R, Ingraham JL, Lin ECC, Low Jr KB, Magasanik B, Reznikoff WS, Riley M, Schaechter M, Umbarger HE "Escherichia coli and Salmonella, Cellular and Molecular Biology, Second Edition." American Society for Microbiology, Washington, D.C., 1996.

Taylor79: Taylor FR, Cronan JE (1979). "Cyclopropane fatty acid synthase of Escherichia coli. Stabilization, purification, and interaction with phospholipid vesicles." Biochemistry 1979;18(15);3292-300. PMID: 380648

Van03: Van Lanen SG, Iwata-Reuyl D (2003). "Kinetic mechanism of the tRNA-modifying enzyme S-adenosylmethionine:tRNA ribosyltransferase-isomerase (QueA)." Biochemistry 42(18);5312-20. PMID: 12731872


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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 18.5 on Sat Dec 20, 2014, BIOCYC14B.