Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
twitter

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

Abbrev Name: ser

Synonyms: S, serine, ser, L-ser

Superclasses: an amino acid or its derivative an amino acid a neutral amino acid
an amino acid or its derivative an amino acid a polar amino acid an uncharged 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
an amino acid or its derivative an amino acid serine

Chemical Formula: C3H7NO3

Molecular Weight: 105.09 Daltons

Monoisotopic Molecular Weight: 105.0425930962 Daltons

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

InChI: InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1

InChIKey: InChIKey=MTCFGRXMJLQNBG-REOHCLBHSA-N

Unification Links: CAS:56-45-1 , ChEBI:33384 , HMDB:HMDB00187 , IAF1260:33717 , KEGG:C00065 , MetaboLights:MTBLC33384 , PubChem:6857581

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -122.1

Reactions known to consume the compound:

cysteine biosynthesis I :
L-serine + acetyl-CoA ↔ O-acetyl-L-serine + coenzyme A

enterobactin biosynthesis :
6 ATP + 3 L-serine + 3 2,3-dihydroxybenzoate → 6 AMP + enterobactin + 6 diphosphate + 3 H+

L-serine degradation :
L-serine → 2-aminoprop-2-enoate + H+ + H2O

selenocysteine biosynthesis I (bacteria) :
tRNAsec + L-serine + ATP + H+ → L-seryl-tRNAsec + AMP + diphosphate

tRNA charging :
tRNAser + L-serine + ATP + H+ → L-seryl-tRNAser + AMP + diphosphate

tryptophan biosynthesis :
indole + L-serine → L-tryptophan + H2O

Not in pathways:
L-serine → pyruvate + ammonium
(1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + L-serine → L-tryptophan + D-glyceraldehyde 3-phosphate + H2O

Reactions known to produce the compound:

serine biosynthesis :
3-phospho-L-serine + H2O → L-serine + phosphate

Not in pathways:
glycerophosphoserine + H2O → sn-glycerol 3-phosphate + L-serine + 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
a protein + H2O → a standard α amino acid + a peptide
amino acids(n) + H2O → a standard α amino acid + amino acids(n-1)
β-aspartyl dipeptide + H2O → L-aspartate + a standard α amino acid
a dipetide with L-aspartate at the N-terminal + H2O → L-aspartate + a standard α amino acid
a tripeptide + H2O → a dipeptide + a standard α amino acid
a dipeptide with proline at the C-terminal + H2O → L-proline + a standard α amino acid
a dipeptide + H2O → 2 a standard α amino acid


a polypeptide + H2O → a polypeptide + an L-amino acid

Reactions known to both consume and produce the compound:

folate polyglutamylation , glycine biosynthesis I , N10-formyl-tetrahydrofolate biosynthesis :
L-serine + a tetrahydrofolate ↔ glycine + a 5,10-methylene-tetrahydrofolate + H2O

phosphatidylethanolamine biosynthesis I :
a CDP-diacylglycerol + L-serine ↔ CMP + an L-1-phosphatidylserine + H+

Not in pathways:
ATP + L-serine ↔ L-seryl-AMP + diphosphate

In Reactions of unknown directionality:

Not in pathways:
'activated' tRNA + L-cysteine = L-serine + tRNA containing a thionucleotide
L-serine + NADP+ = 2-aminomalonate-semialdehyde + NADPH + 2 H+


L-methionine + a 2-oxo carboxylate = 2-oxo-4-methylthiobutanoate + a standard α amino acid


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

In Transport reactions:
Na+[periplasmic space] + L-serine[periplasmic space] → Na+[cytosol] + L-serine[cytosol] ,
L-serine[periplasmic space] + H+[periplasmic space]L-serine[cytosol] + H+[cytosol] ,
an L-amino acid[cytosol]an L-amino acid[periplasmic space]

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

Inhibitor (Competitive) of: D-serine ammonia-lyase [Labow66, Schnackerz99]

Inhibitor (Allosteric) of: α-ketoglutarate reductase [Zhao96] , D-3-phosphoglycerate dehydrogenase [Winicov75]

Inhibitor (Mechanism unknown) of: glutamine synthetase [Comment 1] , phosphoserine phosphatase [Pizer63, Comment 2] , serine acetyltransferase [Kredich66]

In Growth Media: Neidhardt EZ rich defined medium , PMA nitrogen source test + ser , PMA carbon source test + ser


References

Kredich66: Kredich NM, Tomkins GM (1966). "The enzymic synthesis of L-cysteine in Escherichia coli and Salmonella typhimurium." J Biol Chem 1966;241(21);4955-65. PMID: 5332668

Labow66: Labow R, Robinson WG (1966). "Crystalline D-serine dehydrase." J Biol Chem 1966;241(5);1239-43. PMID: 5327101

Pizer63: Pizer LI (1963). "The pathway and control of serine biosynthesis in Escherichia coli." J Biol Chem 1963;238:3934-3944. PMID: 14086727

Schnackerz99: Schnackerz KD, Tai CH, Potsch RK, Cook PF (1999). "Substitution of pyridoxal 5'-phosphate in D-serine dehydratase from Escherichia coli by cofactor analogues provides information on cofactor binding and catalysis." J Biol Chem 274(52);36935-43. PMID: 10601247

Umbarger63: Umbarger HE, Umbarger MA, Siu PML (1963). "Biosynthesis of serine in Escherichia coli and Salmonella typhimurium." J Bacteriol 85:1431-1439. PMID: 14047241

Winicov75: Winicov I (1975). "The mechanism of end product inhibition of serine biosynthesis. V. Mechanism of serim inhibition of phosphoglycerate dehydrogenases." J Biol Chem 250(5);1640-7. PMID: 234462

Zhao96: Zhao G, Winkler ME (1996). "A novel alpha-ketoglutarate reductase activity of the serA-encoded 3-phosphoglycerate dehydrogenase of Escherichia coli K-12 and its possible implications for human 2-hydroxyglutaric aciduria." J Bacteriol 1996;178(1);232-9. PMID: 8550422


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 18.5 on Tue Nov 25, 2014, biocyc13.