Common NameD-glutamate
DescriptionThere are two forms of glutamic acid found in nature: L-glutamic acid and D-glutamic acid. D-glutamic acid, is not endogenously produced in higher mammals. It is found naturally primarily in the cell walls of certain bacteria. D-glutamate is also present in certain foods e.g., soybeans and also arises from the turnover of the intestinal tract microflora, whose cell walls contain significant D-glutamate. Unlike other D-amino acids, D-glutamate is not oxidized by the D-amino acid oxidases, and therefore this detoxification pathway is not available for handling D-glutamate. Likewise, D-glutamic acid, when ingested, largely escapes most deamination reactions (unlike the L-counterpart). Free D-glutamate is found in mammalian tissue at surprisingly high levels, with D-glutamate accounting for 9% of the total glutamate present in liver. D-glutamate is the most potent natural inhibitor of glutathione synthesis identified to date and this may account for its localization to the liver, since circulating D-glutamate may alter redox stabiity (PMID 11158923 ). Certain eels are known to use D-glutamic acid as a phermone for chemical communication. D-Glutamic acid has been found to be a metabolite of Lactobacillus (PMID: 22754309 ).
Structure
Molecular FormulaC5H9NO4
Average Mass147.12930
Monoisotopic Mass147.05316
IUPAC Name(2R)-2-aminopentanedioic acid
Traditional NameD-glutamic acid
CAS Registry Number6893-26-1
SMILES[NH3+][C@H](CCC(=O)[O-])C(=O)[O-]
InChI IdentifierInChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m1/s1
InChI KeyWHUUTDBJXJRKMK-GSVOUGTGSA-N
CHEBI IDCHEBI:29986
HMDB IDHMDB0003339
StateSolid
Water Solubility8.06e+01 g/l
logP-3.54
logS-0.26
pKa (Strongest Acidic)1.88
pKa (Strongest Basic)9.54
Hydrogen Acceptor Count5
Hydrogen Donor Count3
Polar Surface Area100.62 Ų
Rotatable Bond Count4
Physiological Charge-1
Formal Charge0
Refractivity31.29 m³·mol⁻¹
Polarizability13.19

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