iPedia Free Information Center

Information about Aspartic Acid




Chemical structure of L-aspartic acid

Aspartic acid

Systematic (IUPAC) name
(2S)-2-aminobutanedioic acid
Identifiers
CAS number56-84-8
PubChem        5960
Chemical data
FormulaC4H7NO4 
Mol. weight133.10 g/mol
SMILESN[C@@H](CC(O)=O)C(O)=O
Complete data


Aspartic acid or aspartate (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 L-isomer is a protonated varient of 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.

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.

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.

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). [1]

See also


 •  • [ e]
Major families of biochemicals
Peptides | Amino acids | Nucleic acids | Carbohydrates | Lipids | Terpenes | Carotenoids | Tetrapyrroles | Enzyme cofactors | Steroids | Flavonoids | Alkaloids | Polyketides | Glycosides
Analogues of nucleic acids:The 20 Common Amino AcidsAnalogues 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)
IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. It is developed and kept up to date under the auspices of the International Union of Pure and Applied Chemistry (IUPAC).
..... Click the link for more information.
CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. They are also referred to as CAS numbers, CAS RNs or CAS #s.
..... Click the link for more information.
PubChem is a database of chemical molecules. The system is maintained by the National Center for Biotechnology Information (NCBI), a component of the National Library of Medicine, which is part of the United States National Institutes of Health (NIH).
..... Click the link for more information.
A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. A chemical formula is also a short way of showing how a chemical reaction occurs.
..... Click the link for more information.
4, 2
(mildly acidic oxide)
Electronegativity 2.55 (Pauling scale)
Ionization energies
(more) 1st: 1086.5 kJmol−1
2nd: 2352.6 kJmol−1
3rd: 4620.5 kJmol−1

Atomic radius 70 pm
Atomic radius (calc.
..... Click the link for more information.
1, −1
(amphoteric oxide)
Electronegativity 2.20 (Pauling scale) More

Atomic radius 25 pm
Atomic radius (calc.) 53 pm
Covalent radius 37 pm
Van der Waals radius 120 pm
Miscellaneous

Thermal conductivity (300 K) 180.
..... Click the link for more information.
3, 5, 4, 2
(strongly acidic oxide)
Electronegativity 3.04 (Pauling scale)
Ionization energies
(more) 1st: 1402.3 kJmol−1
2nd: 2856 kJmol−1
3rd: 4578.1 kJmol−1

Atomic radius 65 pm
Atomic radius (calc.
..... Click the link for more information.
2, −1
(neutral oxide)
Electronegativity 3.44 (Pauling scale)
Ionization energies
(more) 1st: 1313.9 kJmol−1
2nd: 3388.3 kJmol−1
3rd: 5300.5 kJmol−1

Atomic radius 60 pm
Atomic radius (calc.
..... Click the link for more information.
molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12).
..... Click the link for more information.
smiles

File extension: .smi
Type of format: chemical file format

The simplified molecular input line entry specification or SMILES
..... Click the link for more information.

..... Click the link for more information.
For other articles using the abbreviation or acronym asn see ASN.


Asparagine (abbreviated as Asn or N; Asx or B
..... Click the link for more information.
amino acid is a molecule that contains both amine and carboxyl functional groups. In biochemistry, this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent.
..... Click the link for more information.
A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. A chemical formula is also a short way of showing how a chemical reaction occurs.
..... Click the link for more information.
Proteinogenic amino acids, also known as standard, normal, or primary amino acids, are those 20 amino acids that are found in proteins and that are coded for in the standard genetic code. Proteinogenic literally means protein building.
..... Click the link for more information.
Proteins are large organic compounds made of amino acids arranged in a linear chain and joined together by peptide bonds between the carboxyl and amino groups of adjacent amino acid residues.
..... Click the link for more information.
Glutamic acid or glutamate (abbreviated as Glu or E; Glx or Z represents either glutamic acid or glutamine), is the protonated form of glutamate (the anion). Glutamate is one of the 20 proteinogenic amino acids.
..... Click the link for more information.
Mammalia
Linnaeus, 1758

Subclasses & Infraclasses
  • Subclass †Allotheria*
  • Subclass Prototheria
  • Subclass Theria

..... Click the link for more information.
Oxaloacetic acid is an organic compound with the chemical formula HO2CC(O)CH2CO2H. It also has other names (see Table) and its conjugate base is called "oxaloacetate.
..... Click the link for more information.
Transamination (or aminotransfer) is the reaction between an amino acid and an alpha-keto acid. The amino group is transferred from the former to the latter; this results in the amino acid being converted to the corresponding α-keto acid, while the reactant α-keto acid is
..... Click the link for more information.
Methionine (abbreviated as Met or M)[1] is an α-amino acid with the chemical formula HO2CCH(NH2)CH2CH2SCH3. This essential amino acid is classified as nonpolar.
..... Click the link for more information.
Threonine (abbreviated as Thr or T)[1] is an α-amino acid with the chemical formula HO2CCH(NH2)CH(OH)CH3. Its codons are ACU and ACA. This essential amino acid is classified as polar.
..... Click the link for more information.
Isoleucine (abbreviated as Ile or I)[1] is an α-amino acid with the chemical formula HO2CCH(NH2)CH(CH3)CH2CH3.
..... Click the link for more information.
Lysine (abbreviated as Lys or K)[1] is an α-amino acid with the chemical formula HO2CCH(NH2)(CH2)4NH2.
..... Click the link for more information.
For other articles using the abbreviation or acronym asn see ASN.


Asparagine (abbreviated as Asn or N; Asx or B
..... Click the link for more information.
Glutamine (abbreviated as Gln or Q; Glx or Z represents either glutamine or glutamic acid) is one of the 20 amino acids encoded by the standard genetic code.
..... Click the link for more information.
Glutamic acid or glutamate (abbreviated as Glu or E; Glx or Z represents either glutamic acid or glutamine), is the protonated form of glutamate (the anion). Glutamate is one of the 20 proteinogenic amino acids.
..... Click the link for more information.
Metabolomics is the "systematic study of the unique chemical fingerprints that specific cellular processes leave behind" - specifically, the study of their small-molecule metabolite profiles.
..... Click the link for more information.
The urea cycle (also known as the ornithine cycle) is a cycle of biochemical reactions occurring in many animals that produces urea from ammonia (NH3). This cycle was the first metabolic cycle discovered (Krebs and Kurt Henseleit, 1932).
..... Click the link for more information.
Gluconeogenesis is the generation of glucose from non-sugar carbon substrates like pyruvate, lactate, glycerol, and glucogenic amino acids (primarily alanine and glutamine).
..... Click the link for more information.


This article is copied from an article on Wikipedia.org - the free encyclopedia created and edited by online user community. The text was not checked or edited by anyone on our staff. Although the vast majority of the wikipedia encyclopedia articles provide accurate and timely information please do not assume the accuracy of any particular article. This article is distributed under the terms of GNU Free Documentation License.
Herod_Archelaus


page counter