| Aspartic acid (symbol Asp or D; the ionic form is known as aspartate), is an α-amino acid that is used in the biosynthesis of proteins. 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. 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.
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. Under physiological conditions (pH 7.4) in proteins the side chain usually occurs as the negatively charged aspartate form, −COO−. 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, with the proposed mnemonic asparDic acid. |
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| InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9) |
| CKLJMWTZIZZHCS-UHFFFAOYSA-N |
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Daphnia magna
(NCBI:txid35525)
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See:
Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyondTine Vandenbrouck, Oliver A.H. Jones, Nathalie Dom, Julian L. Griffin, Wim De CoenEnvironment International 36 (2010) 254-268
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Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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fundamental metabolite
Any metabolite produced by all living cells.
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View more via ChEBI Ontology
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(+-)-Aspartic acid
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ChemIDplus
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(R,S)-Aspartic acid
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ChemIDplus
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2-aminobutanedioic acid
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IUPAC
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Asp
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ChEBI
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Aspartic acid
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KEGG COMPOUND
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D
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ChEBI
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DL-Aminosuccinic acid
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ChemIDplus
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DL-Asparagic acid
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ChemIDplus
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185140
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Gmelin Registry Number
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Gmelin
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617-45-8
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CAS Registry Number
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NIST Chemistry WebBook
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617-45-8
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CAS Registry Number
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ChemIDplus
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774618
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Reaxys Registry Number
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Reaxys
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