Trivial: Aspartic acid
Systematic: 2-Aminobutanedioic acid
Aminosuccinic acid, asparagic acid, asparaginic acid
|3D model (Jmol)||Interactive image
|Molar mass||133.10 g·mol−1|
|Melting point||270 °C (518 °F; 543 K)|
|Boiling point||324 °C (615 °F; 597 K) (decomposes)|
|Safety data sheet||See: data page|
|Supplementary data page|
|Refractive index (n),
Dielectric constant (εr), etc.
|UV, IR, NMR, MS|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Aspartic acid (abbreviated as Asp or D; encoded by the codons [GAU and GAC]), also known as aspartate, is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH+
3 form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO− form under biological conditions), and a side chain CH2COOH. Under physiological conditions in proteins the sidechain usually occurs as the negatively charged aspartate form, −COO−. It is semi-essential in humans, meaning the body can synthesize it from oxaloacetate.
Asp's L-isomer is one of the 23 proteinogenic amino acids, i.e., the building blocks of proteins. Asp (and glutamic acid) is classified as acidic, with a pKa of 3.9, however in a peptide this is highly dependent on the local environment (as with all amino acids), and could be as high as 14. Asp is pervasive in biosynthesis.
Aspartic acid was first discovered in 1827 by Auguste-Arthur Plisson and Étienne Ossian Henry, derived from asparagine, which had been isolated from asparagus juice in 1806, by boiling with a base.
Forms and nomenclature
There are two forms or enantiomers of aspartic acid. The name "aspartic acid" can refer to either enantiomer or a mixture of two. Of these two forms, only one, "L-aspartic acid", is directly incorporated into proteins. The biological roles of its counterpart, "D-aspartic acid" are more limited. Where enzymatic synthesis will produce one or the other, most chemical syntheses will produce both forms, "DL-aspartic acid," known as a racemic mixture.
Aspartate is non-essential in mammals, being produced from oxaloacetate by transamination. It can also be generated from ornithine and citrulline in the urea cycle. In plants and microorganisms, aspartate is the precursor to several amino acids, including four that are essential for humans: methionine, threonine, isoleucine, and lysine. The conversion of aspartate to these other amino acids begins with reduction of aspartate to its "semialdehyde," O2CCH(NH2)CH2CHO. Asparagine is derived from aspartate via transamidation:
- -O2CCH(NH2)CH2CO2- + GC(O)NH3+ O2CCH(NH2)CH2CONH3+ + GC(O)O
Other biochemical roles
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. Aspartate donates one nitrogen atom in the biosynthesis of inosine, the precursor to the purine bases. In addition, aspartic acid acts as hydrogen acceptor in a chain of ATP synthase.
Interactive pathway map
Click on genes, proteins and metabolites below to link to respective articles. [§ 1]
- The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534".
Applications & Market
The global market for aspartic acid is $117MM annually (50-60K MT/Yr) with areas of growth accounting for an addressable market of $8.78BB. The three largest market segments include the U.S., Western Europe, and China. Current applications include biodegradable polymers (polyaspartate), low calorie sweeteners, scale and corrosion inhibitors, and resins.
Nearly all aspartic acid is manufactured in China.
One area of aspartic acid market growth is biodegradable superabsorbent polymers (SAP). The super absorbent polymers market is anticipated to grow at a CAGR of 5.5% from 2014 to 2019 to reach a value of $8.78BB globally. Around 75% of superabsorbent polymers are used in disposable diapers and an additional 20% is used for adult incontinence and feminine hygiene products. Polyaspartate, the polymerization product of aspartic acid, is a biodegradable substitute to polyacrylate. The polyaspartate market comprises a small fraction (est. < 1%) of the total SAP market.
In addition to SAP, aspartic acid has applications in the $19B fertilizer industry, where polyaspartate improves water retention and nitrogen uptake; the $1.1B (2020) concrete floor coatings market, where polyaspartic is a low VOC, low energy alternative to traditional epoxy resins; and lastly the >$5B scale and corrosion inhibitors market.
- Aspartic acid is known to have a use in the synthesis of Lorglumide.
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:
- Animal sources: oysters, luncheon meats, sausage meat, wild game
- Vegetable sources: sprouting seeds, oat flakes, avocado, asparagus, young sugarcane, and molasses from sugar beets.
- Dietary supplements, either as aspartic acid itself or salts (such as magnesium aspartate)
- The sweetener aspartame (brands: NutraSweet, Equal, Canderel, etc.)
The major disadvantage of the above technique is that equimolar amounts of each enantiomer are made. Using biotechnology it is now possible to use immobilised enzymes to create just one type of enantiomer owing to their stereospecificity.
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- GMD MS Spectrum
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