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Escherichia coli K-12 substr. MG1655 Compound: D-glutamate

Abbrev Name: D-glt

Synonyms: D-glutamic acid, D-glu

Superclasses: an acid all carboxy acids a carboxylate an amino acid a D-amino acid
an acid all carboxy acids a carboxylate an amino acid a glutamate
an amino acid or its derivative an amino acid a D-amino acid
an amino acid or its derivative an amino acid a glutamate

Chemical Formula: C5H8NO4

Molecular Weight: 146.12 Daltons

Monoisotopic Molecular Weight: 147.0531577825 Daltons

D-glutamate compound structure

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

InChI: InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/p-1/t3-/m1/s1

InChIKey: InChIKey=WHUUTDBJXJRKMK-GSVOUGTGSA-M

Unification Links: CAS:6893-26-1 , ChEBI:29986 , HMDB:HMDB03339 , IAF1260:34285 , KEGG:C00217 , PubChem:5460297

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -166.7

Reactions known to consume the compound:

UDP-N-acetylmuramoyl-pentapeptide biosynthesis I (meso-diaminopimelate containing) :
D-glutamate + UDP-N-acetyl-α-D-muramoyl-L-alanine + ATP → UDP-N-acetyl-α-D-muramoyl-L-alanyl-D-glutamate + ADP + phosphate + H+

Not in pathways:
a D-amino acid + an electron-transfer quinone[inner membrane] + H2O → ammonium + a 2-oxo carboxylate + an electron-transfer quinol[inner membrane]

Reactions known to produce the compound:

Not in pathways:
a D-aminoacyl-[tRNA] + H2O → a D-amino acid + an uncharged tRNA + 2 H+

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:

UDP-N-acetylmuramoyl-pentapeptide biosynthesis I (meso-diaminopimelate containing) :
L-glutamate ↔ D-glutamate

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]

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 Redox half-reactions:
a 2-oxo carboxylate[in] + ammonium[in] + 2 H+[in] + 2 e-[membrane]a D-amino acid[in] + H2O[in]

Enzymes inhibited by D-glutamate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: glutamate dehydrogenase [McPherson88]

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

This compound has been characterized as an alternative substrate of the following enzymes: transport of glutamate , glutamate-cysteine ligase

In Growth Media: PMA nitrogen source test + D-glutamate


References

McPherson88: McPherson MJ, Baron AJ, Jones KM, Price GJ, Wootton JC (1988). "Multiple interactions of lysine-128 of Escherichia coli glutamate dehydrogenase revealed by site-directed mutagenesis studies." Protein Eng 2(2);147-52. PMID: 3149742

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


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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 19.0 on Thu Jul 2, 2015, biocyc12.