Aspartic acid






Chemical structure of L-aspartic acid

Aspartic acid

Systematic (IUPAC) name
(2S)-2-aminobutanedioic acid
Identifiers
CAS number 56-84-8
PubChem         5960
Chemical data
Formula O4 
Molar mass 133.10 g/mol
SMILES N[C@@H](CC(O)=O)C(O)=O
Complete data

Aspartic acid (abbreviated as Asp or D)[1] is an α-glutamic acid. Aspartic acid is pervasive in biosynthesis. As with all amino acids, the location of acid protons depends on the pH of the solution and the crystallization conditions.

The abbreviation Asx (or B) represent either aspartic acid or asparagine.

Role in biosynthesis of amino acids

Aspartic acid is non-essential in mammals, being produced from Asparagine is derived from aspartic acid via transamidation:

HO2CCH(NH2)CH2CO2H + GC(O)NH2 HO2CCH(NH2)CH2CONH2 + GC(O)OH

(where GC(O)NH2 and GC(O)OH are glutamic acid, respectively)

Other biochemical roles

Aspartic acid is also a purine bases.

Neurotransmitter

Aspartate (the excitotoxin[citation needed].

As a neurotransmitter, aspartic acid may provide resistance to fatigue, and, thus, leads to endurance, although the evidence to support this idea is not strong.

Sources

Dietary Sources

Aspartic acid is not an essential amino acid, which means that it can be synthesized from central metabolic pathway intermediates in humans and is not required in the diet. Aspartic acid is found in:

  • Animal sources: luncheon meats, sausage meat, wild game
  • Vegetarian sources: sprouting seeds, oat flakes, avocado, asparagus.

Chemical Synthesis

Racemic aspartic acid can be synthesized from diethyl sodium phthalimidomalonate, (C6H4(CO)2NC(CO2Et)2).[4]

References

  1. ^ IUPAC-IUBMB Joint Commission on Biochemical Nomenclature. Nomenclature and Symbolism for Amino Acids and Peptides. Recommendations on Organic & Biochemical Nomenclature, Symbols & Terminology etc. Retrieved on 2007-05-17.
  2. ^ Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.
  3. ^ Philip E. Chen, Matthew T. Geballe, Phillip J. Stansfeld, Alexander R. Johnston, Hongjie Yuan, Amanda L. Jacob, James P. Snyder, Stephen F. Traynelis, and David J. A. Wyllie. 2005. Structural Features of the Glutamate Binding Site in Recombinant NR1/NR2A N-Methyl-D-aspartate Receptors Determined by Site-Directed Mutagenesis and Molecular Modeling. Molecular Pharmacology. Volume 67, Pages 1470-1484.
  4. ^ Dunn, M. S.; Smart, B. W. “DL-Aspartic Acid”Organic Syntheses, Collected Volume 4, p.55 (1963). http://www.orgsyn.org/orgsyn/pdfs/CV4P0055.pdf

See also

  • Aspartate transaminase
  • Sodium poly(aspartate), a synthetic polyamide
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Aspartic_acid". A list of authors is available in Wikipedia.