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aspartic acid

 
Dictionary: as·par·tic acid   (ə-spär'tĭk) pronunciation
n.
A nonessential amino acid, C4H7NO4, found especially in young sugar cane and sugar-beet molasses.

[From ASPARAGUS (from its being obtained from an amino acid found in asparagus).]


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One of the nonessential amino acids, found in many proteins and closely related to asparagine. It is used in medical and biochemical research, as an organic intermediate, and in various industrial applications. It is one of the two components of aspartame.

For more information on aspartic acid, visit Britannica.com.

Food and Nutrition: aspartic acid
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aspartate

A non-essential amino acid.

 
Columbia Encyclopedia: aspartic acid
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aspartic acid (əspär'tĭk), organic compound, one of the 20 amino acids commonly found in animal proteins. Only the L-stereoisomer participates in the biosynthesis of proteins. Its acidic side chain adds a negative charge and hence a greater degree of water-solubility to proteins in neutral solution and has been shown to be near the active sites of some enzymes (see pepsin). Aspartic acid is not essential to the human diet. It was discovered in protein in 1868.


Veterinary Dictionary: aspartic acid
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A nonessential dicarboxylic amino acid, widely distributed in proteins.

Wikipedia: Aspartic acid
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Aspartic acid
Asparaginsäure - Aspartic acid.svg
IUPAC name
Other names 2-Aminobutanedioic acid
Identifiers
CAS number 617-45-8 Yes check.svgY,
56-84-8 (L-isomer)
1783-96-6 (D-isomer)
PubChem 424
EC-number 200-291-6
SMILES
InChI
InChI key CKLJMWTZIZZHCS-UHFFFAOYAE
ChemSpider ID 411
Properties
Molecular formula C4H7NO4
Molar mass 133.1 g mol−1
Hazards
MSDS External MSDS
EU Index not listed
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Aspartic acid (abbreviated as Asp or D; Asx or B represent either aspartic acid or asparagine)[1] is an α-amino acid with the chemical formula HO2CCH(NH2)CH2CO2H. The carboxylate anion of aspartic acid is known as aspartate. The L-isomer of aspartate is one of the 20 proteinogenic amino acids, i.e., the building blocks of proteins. Its codons are GAU and GAC.

Aspartic acid is, together with glutamic acid, classified as an acidic amino acid with a pKa of 4.0. 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.

Contents

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

A representation of the structure of L-aspartic acid.

Aspartate 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.

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. Aspartic acid is found in:

Chemical synthesis

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

References

  1. ^ "Nomenclature and symbolism for amino acids and peptides (IUPAC-IUB Recommendations 1983)", Pure Appl. Chem. 56 (5): 595–624, 1984, doi:10.1351/pac198456050595 .
  2. ^ Lehninger, Albert L.; Nelson, David L.; Cox, Michael M. (2000), Principles of Biochemistry (3rd ed.), New York: W. H. Freeman, ISBN 1-57259-153-6 .
  3. ^ Chen, Philip E.; Geballe, Matthew T.; Stansfeld, Phillip J.; Johnston, Alexander R.; Yuan, Hongjie; Jacob, Amanda L.; Snyder, James P.; Traynelis, Stephen F. et al. (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", Mol. Pharmacol. 67 (5): 1470–84, doi:10.1124/mol.104.008185, http://molpharm.aspetjournals.org/cgi/content/full/67/5/1470 .
  4. ^ Dunn, M. S.; Smart, B. W. (1950), "DL-Aspartic Acid", Org. Synth. 30: 7, http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV4P0055 ; Coll. Vol. 4: 55 .

See also


 
 

 

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Dictionary. The American Heritage® Dictionary of the English Language, Fourth Edition Copyright © 2007, 2000 by Houghton Mifflin Company. Updated in 2009. Published by Houghton Mifflin Company. All rights reserved.  Read more
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Food and Nutrition. A Dictionary of Food and Nutrition. Copyright © 1995, 2003, 2005 by A. E. Bender and D. A. Bender. All rights reserved.  Read more
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Veterinary Dictionary. Saunders Comprehensive Veterinary Dictionary 3rd Edition. Copyright © 2007 by D.C. Blood, V.P. Studdert and C.C. Gay, Elsevier. All rights reserved.  Read more
Wikipedia. This article is licensed under the Creative Commons Attribution/Share-Alike License. It uses material from the Wikipedia article "Aspartic acid" Read more