L Deprotonated zwitterion (aspartate): C(C(C(=O)[O-])[NH3+])C(=O)[O-]
Properties
Chemical formula
C4H7NO4
Molar mass
133.103 g·mol−1
Appearance
colourless crystals
Density
1.7 g/cm3
Melting point
270 °C (518 °F; 543 K)
Boiling point
324 °C (615 °F; 597 K) (decomposes)
Solubility in water
4.5 g/L[2]
Acidity (pKa)
1.99 (α-carboxyl; H2O)
3.90 (side chain; H2O)
9.90 (amino; H2O)[3]
Conjugate base
Aspartate
Magnetic susceptibility (χ)
-64.2·10−6 cm3/mol
Hazards
NFPA 704 (fire diamond)
1
1
0
Supplementary data page
Aspartic acid (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
Aspartic acid (symbol Asp or D;[4] the ionic form is known as aspartate), is an α-amino acid that is used in the biosynthesis of proteins.[5] The L-isomer of aspartic acid is one of the 22 proteinogenic amino acids, i.e., the building blocks of proteins.
D-aspartic acid is one of two D-amino acids commonly found in mammals.[6][7] Apart from a few rare exceptions, D-aspartic acid is not used for protein synthesis but is incorporated into some peptides and plays a role as a neurotransmitter/neuromodulator.[6]
Like all other amino acids, aspartic acid contains an amino group and a carboxylic acid. Its α-amino group is in the protonated –NH+ 3 form under physiological conditions, while its α-carboxylic acid group is deprotonated −COO− under physiological conditions. Aspartic acid has an acidic side chain (CH2COOH) which reacts with other amino acids, enzymes and proteins in the body.[5] Under physiological conditions (pH 7.4) in proteins the side chain usually occurs as the negatively charged aspartate form, −COO−.[5] It is a non-essential amino acid in humans, meaning the body can synthesize it as needed. It is encoded by the codons GAU and GAC.
In proteins aspartate sidechains are often hydrogen bonded to form asx turns or asx motifs, which frequently occur at the N-termini of alpha helices.
Aspartic acid, like glutamic acid, is classified as an acidic amino acid, with a pKa of 3.9; however, in a peptide this is highly dependent on the local environment, and could be as high as 14.
The one-letter code D for aspartate was assigned arbitrarily,[8] with the proposed memnonic asparDic acid.[9]
^Budavari, Susan; Co, Merck (1989). "862. Aspartic acid". The Merck Index (11th ed.). Merck. p. 132. ISBN 978-0-911910-28-5.
^"ICSC 1439 - L-ASPARTIC ACID". inchem.org.
^Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.
^"Nomenclature and Symbolism for Amino Acids and Peptides". IUPAC-IUB Joint Commission on Biochemical Nomenclature. 1983. Archived from the original on 9 October 2008. Retrieved 5 March 2018.
^ abcG., Voet, Judith; W., Pratt, Charlotte (2016-02-29). Fundamentals of biochemistry : life at the molecular level. John Wiley & Sons. ISBN 9781118918401. OCLC 910538334.{{cite book}}: CS1 maint: multiple names: authors list (link)
^ abD'Aniello, Antimo (1 February 2007). "d-Aspartic acid: An endogenous amino acid with an important neuroendocrine role". Brain Research Reviews. 53 (2): 215–234. doi:10.1016/j.brainresrev.2006.08.005. PMID 17118457. S2CID 12709991.
^Huang AS, Beigneux A, Weil ZM, Kim PM, Molliver ME, Blackshaw S, Nelson RJ, Young SG, Snyder SH (March 2006). "D-aspartate regulates melanocortin formation and function: behavioral alterations in D-aspartate oxidase-deficient mice". The Journal of Neuroscience. 26 (10): 2814–9. doi:10.1523/JNEUROSCI.5060-05.2006. PMC 6675153. PMID 16525061.
^"IUPAC-IUB Commission on Biochemical Nomenclature A One-Letter Notation for Amino Acid Sequences". Journal of Biological Chemistry. 243 (13): 3557–3559. 10 July 1968. doi:10.1016/S0021-9258(19)34176-6.
^Adoga, Godwin I; Nicholson, Bh (January 1988). "Letters to the editor". Biochemical Education. 16 (1): 49. doi:10.1016/0307-4412(88)90026-X.
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asparagine and asparticacid itself are decomposed with a remarkable ease under the influence of nitrous acid, rendering nitrogen gas and malic acid.) Plimmer...
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dicarboxylic acid in the industry is adipic acid, which is a precursor in the production of nylon. Other examples of dicarboxylic acids include asparticacid and...
also arise from trans- or de- amination of asparticacid. Oxaloacetate is an intermediate of the citric acid cycle, where it reacts with acetyl-CoA to...
acid or maleic acid, which proceeds as follows: (S,S)-EDDS is produced stereospecifically by the alkylation of an ethylenedibromide with L-aspartic acid...
main amino acids involved are serine, histidine, and asparticacid. They all play a role in cleaving the peptide bond. These three amino acids are known...
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a sodium salt of iminodisuccinic acid, also referred to as N-(1,2-dicarboxyethyl)asparticacid. Iminodisuccinic acid can be prepared by reacting maleic...
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measure up to 9 amino acids useful in geochronology over different time scales on a single chromatogram (asparticacid, glutamic acid, serine, alanine, arginine...
pyridoxamine in the first phase of the reaction, when an amino acid is converted into a keto acid.[citation needed] ALT is commonly measured clinically as part...
environments, like the aspartic protease pepsin in mammalian stomachs, may have catalytic aspartate or glutamate residues that act as Brønsted acids. There are three...
and is a zwitterion, with the exception of amino acids with basic or acidic side chains. Asparticacid, for example, possesses one protonated amine and...
the amino acids asparagine or glutamine is removed or converted to another functional group. Typically, asparagine is converted to asparticacid or isoaspartic...
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