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Aspartic acid (abbreviated as Asp or D; Asx or B represent either aspartic acid or asparagine
Asparagine

Asparagine is one of the 20 most common natural amino acids on Earth. It has carboxamide as the side chain's functional group. It is not an essential amino acid....
) is an a-amino acid
Amino acid

In chemistry, an amino acid is a molecule containing both amine and carboxyl functional groups. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent....
 with the chemical formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
 HO2CCH(NH2)CH2CO2H. The carboxylate anion
Carboxylate anion

A carboxylate anion is an ion with negative chargethat contains the group -COO−. It is the conjugate base of a carboxylic acid....
 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 protein
Protein

Proteins are 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 Residue ....
s. Its codons are GAU and GAC.

Aspartic acid is, together with glutamic acid
Glutamic acid

Glutamic acid is one of the 20 proteinogenic amino acids and its codons are GAA and GAG. It is a non-essential amino acid. The carboxylate anions and salt of glutamic acid are known as glutamates....
, classified as an acidic amino acid with a pKa
PKA

PKA or pKa may be:* Protein kinase A, a cAMP activated protein kinase* pKa, the symbol for Acid dissociation constant...
 of 4.0.






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Aspartic acid (abbreviated as Asp or D; Asx or B represent either aspartic acid or asparagine
Asparagine

Asparagine is one of the 20 most common natural amino acids on Earth. It has carboxamide as the side chain's functional group. It is not an essential amino acid....
) is an a-amino acid
Amino acid

In chemistry, an amino acid is a molecule containing both amine and carboxyl functional groups. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent....
 with the chemical formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
 HO2CCH(NH2)CH2CO2H. The carboxylate anion
Carboxylate anion

A carboxylate anion is an ion with negative chargethat contains the group -COO−. It is the conjugate base of a carboxylic acid....
 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 protein
Protein

Proteins are 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 Residue ....
s. Its codons are GAU and GAC.

Aspartic acid is, together with glutamic acid
Glutamic acid

Glutamic acid is one of the 20 proteinogenic amino acids and its codons are GAA and GAG. It is a non-essential amino acid. The carboxylate anions and salt of glutamic acid are known as glutamates....
, classified as an acidic amino acid with a pKa
PKA

PKA or pKa may be:* Protein kinase A, a cAMP activated protein kinase* pKa, the symbol for Acid dissociation constant...
 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.

Role in biosynthesis of amino acids

Aspartic acid is non-essential in mammal
Mammal

Mammals are a class of vertebrate animals whose name is derived from their distinctive feature, mammary glands, with which they feed their young....
s, being produced from oxaloacetate by transamination
Transamination

There are two chemical reactions known as transamination . The first 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 a-keto acid, while the reactant a-keto acid is converted to the corresponding amin...
. In plants and microorganism
Microorganism

A microorganism or microbe is an organism that is microscopic . The study of microorganisms is called microbiology, a subject that began with Anton van Leeuwenhoek's discovery of microorganisms in 1675, using a microscope of his own design....
s, aspartic acid is the precursor to several amino acids, including four that are essential: methionine
Methionine

Methionine is an a-amino acid with the chemical formula HO2CCHCH2CH2SCH3. This Essential amino acid is classified as nonpolar....
, threonine
Threonine

Threonine is an a-amino acid with the chemical formula HO2CCHCHCH3. Its codons are ACU, ACA, ACC, and ACG. This essential amino acid is classified as Chemical polarity....
, isoleucine
Isoleucine

Isoleucine is an a-amino acid with the chemical formula HO2CCHCHCH2CH3. It is an essential amino acid, which means that humans cannot synthesize it, so it must be part of our diet....
, and lysine
Lysine

Lysine is an a-amino acid with the chemical formula HO2CCH4NH2. This amino acid is an essential amino acid, which means that humans cannot synthesize it....
. The conversion of aspartic acid to these other amino acids begins with reduction of aspartic acid to its "semialdehyde," HO2CCH(NH2)CH2CHO. Asparagine
Asparagine

Asparagine is one of the 20 most common natural amino acids on Earth. It has carboxamide as the side chain's functional group. It is not an essential amino acid....
 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
Glutamine

Glutamine is one of the 20 amino acids encoded by the standard genetic code. Its side chain is an amide formed by replacing the side-chain hydroxyl of glutamic acid with an amine functional group....
 and glutamic acid
Glutamic acid

Glutamic acid is one of the 20 proteinogenic amino acids and its codons are GAA and GAG. It is a non-essential amino acid. The carboxylate anions and salt of glutamic acid are known as glutamates....
, respectively)

Other biochemical roles

Aspartate is also a metabolite
Metabolite

Metabolites are the intermediates and products of metabolism. The term metabolite is usually restricted to small molecules. A primary metabolite is directly involved in normal growth, development, and reproduction....
 in the urea cycle
Urea cycle

The urea cycle is a cycle of biochemistry reactions occurring in many animals that produces urea 2carbonoxygen from ammonia . This cycle was the first metabolic cycle discovered ....
 and participates in gluconeogenesis
Gluconeogenesis

Gluconeogenesis is a metabolic pathway that results in the generation of glucose from non-carbohydrate carbon substrates such as lactic acid, glycerol, and glucogenic amino acids....
. It carries reducing equivalents in the malate-aspartate shuttle
Malate-aspartate shuttle

The malate-aspartate shuttle is a biochemical system for translocating electrons produced during glycolysis across the impermeable inner membrane of the mitochondrion for oxidative phosphorylation in eukaryotes....
, 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
Inositol

Inositol, , is a carbocyclic polyol that plays an important role as the structural basis for a number of secondary messengers in Eukaryote cell s, including inositol phosphates, phosphatidylinositol and phosphatidylinositol phosphate lipids....
, the precursor to the purine
Purine

Purine is a heterocyclic compound aromatic organic compound, consisting of a pyrimidine ring fused to an imidazole ring. Purines, including substituted purines and their tautomers, are the most widely distributed kind of nitrogen-containing heterocycle in nature....
 bases.

Neurotransmitter
Aspartate (the conjugate base of aspartic acid) stimulates NMDA receptor
NMDA receptor

The NMDA receptor is an ionotropic receptor for glutamate . Activation of NMDA receptors results in the opening of an ion channel that is nonselective to ion....
s, though not as strongly as the amino acid neurotransmitter glutamate
Glutamic acid

Glutamic acid is one of the 20 proteinogenic amino acids and its codons are GAA and GAG. It is a non-essential amino acid. The carboxylate anions and salt of glutamic acid are known as glutamates....
 does. It serves as an excitatory neurotransmitter
Neurotransmitter

Neurotransmitters are chemistry which relay, amplify and modulate signals between a neuron and another cell . Neurotransmitters are packaged into vesicles that cluster beneath the membrane on the presynaptic side of a synapse, and are released into the synaptic cleft, where they bind to receptors in the membrane on the postsynaptic side of...
 in the brain and is an excitotoxin.

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
Essential amino acid

File:BakedFish.jpgAn essential amino acid or indispensable amino acid is an amino acid that cannot be synthesized de novo synthesis by the organism , and therefore must be supplied in the diet....
, which means that it can be synthesized from central metabolic pathway intermediates in humans. Aspartic acid is found in:
  • Animal sources: luncheon meats, sausage meat, wild game
  • Vegetable sources: sprouting seeds, oat flakes, avocado
    Avocado

    The avocado , also known as palta or aguacate , butter pear or alligator pear, is a tree native to Mexico, South America and Central America, classified in the flowering plant family Lauraceae....
    , asparagus
    Asparagus

    Asparagus officinalis is a flowering plant species in the genus Asparagus from which the vegetable known as asparagus is obtained....
    .
  • Dietary supplements


Chemical synthesis

Racemic
Racemic

In chemistry, a racemic mixture, or racemate, is one that has equal Amount of substance of left- and right-handed enantiomer of a Chirality molecule....
 aspartic acid can be synthesized from diethyl sodium phthalimidomalonate, (C6H4(CO)2NC(CO2Et)2).

See also

  • Aspartate transaminase
    Aspartate transaminase

    Aspartate transaminase also called serum glutamic oxaloacetic transaminase or aspartate aminotransferase is similar to alanine transaminase in that it is another enzyme associated with liver parenchymal cells....
  • Sodium poly(aspartate)
    Sodium poly(aspartate)

    Sodium poly is a condensation polymer based on aspartic acid. The polymerization reaction is an example of a step-growth polymerization to a polyamide and in one practical procedure aspartic acid is simply heated to 180 ?C resulting in water release and the formation of a poly with succinimide repeating units....
    , a synthetic polyamide
    Polyamide

    A polyamide is a polymer containing monomers of amides joined by peptide bonds. They can occur both naturally, examples being proteins, such as wool and silk, and can be made artificially, examples being nylons, aramids, and sodium poly....