Aspartate

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Structural formula of aspartic acid

3D stick model of aspartic acid
Chemical structure of L-aspartic acid

Aspartate

Systematic (IUPAC) name
(2S)-2-aminobutanedioic acid
Identifiers
CAS number 56-84-8
PubChem         5960
Chemical data
Formula C4H7NO4 
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-amino acid with the chemical formula HO2CCH(NH2)CH2CO2H. The L-isomer is one of the 20 proteinogenic amino acids, i.e. the building blocks of proteins. Its codons are GAU and GAC. It is classified as an acidic amino acid, together with glutamic acid. Aspartic acid is pervasive in biosynthesis. Like 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 oxaloacetate by transamination. In plants and microorganisms, aspartic acid is the precursor to several amino acids, including four that are essential: methionine, threonine, isoleucine, and lysine. The conversion of aspartic acid to these other amino acids begins with reduction of aspartic acid to its "semialdehyde," HO2CCH(NH2)CH2CHO.[2] 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 glutamine and glutamic acid, respectively)

Other biochemical roles

Aspartic acid is also a metabolite in the urea cycle and participates in gluconeogenesis. It carries reducing equivalents in the malate-aspartate shuttle, which utilizes the ready interconversion of aspartate and oxaloacetate, which is the oxidized (dehydrogenated) derivative of malic acid. Aspartic acid donates one nitrogen atom in the biosynthesis of inositol, the precursor to the purine bases.

Neurotransmitter

Aspartate (the conjugate base of aspartic acid) stimulates NMDA receptors, though not as strongly as the amino acid neurotransmitter glutamate does.[3] It serves as an excitatory neurotransmitter in the brain and is an excitotoxin Template:Fix/category[citation needed].

As a neurotransmitter, aspartic acid may provide resistance to fatigue and thus lead 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 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


v  d  e
Major families of biochemicals
Peptides | Amino acids | Nucleic acids | Carbohydrates | Nucleotide sugars | Lipids | Terpenes | Carotenoids | Tetrapyrroles | Enzyme cofactors | Steroids | Flavonoids | Alkaloids | Polyketides | Glycosides
Analogues of nucleic acids:The 20 Common Amino Acids ("dp" = data page)Analogues of nucleic acids:
Alanine (dp) | Arginine (dp) | Asparagine (dp) | Aspartic acid (dp) | Cysteine (dp) | Glutamic acid (dp) | Glutamine (dp) | Glycine (dp) | Histidine (dp) | Isoleucine (dp) | Leucine (dp) | Lysine (dp) | Methionine (dp) | Phenylalanine (dp) | Proline (dp) | Serine (dp) | Threonine (dp) | Tryptophan (dp) | Tyrosine (dp) | Valine (dp)

bn:অ্যাস্পার্টিক অ্যাসিড ca:Àcid aspàrtic cs:Kyselina asparagová de:Asparaginsäure eo:Asparta acido ko:아스파르트산 id:Asam aspartat it:Acido aspartico he:חומצה אספרטית lv:Asparagīnskābe lb:Aspartat lt:Asparto rūgštis hu:Aszparaginsav nl:Asparaginezuur fi:Asparagiinihappo sv:Asparaginsyra uk:Аспарагінова кислота


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