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14-September-2008 18:38:39 - Aspartic acid Structural formula of aspartic acid 3D stick model of aspartic acid Chemical structure of L-aspartic acid Aspartic acid Systematic IUPAC name 2S-2-aminobutanedioic acid Identifiers CAS number 56-84-8 PubChem 5960 Chemical data Formula C4H7NO4 Molar mass 133.10 g/mol SMILES NC@@HCCO=OCO=O Complete data Aspartic acid abbreviated as Asp or D; Asx or B represent either aspartic acid or asparagine1 is an α-amino acid with the chemical formula HO2CCHNH2CH2CO2H. The carboxylate anion 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 proteins. Its codons are GAU and GAC. Aspartic acid is, together with glutamic acid, classified as an acidic amino acid with a pKa 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. Contents 1 Role in biosynthesis of amino acids 2 Other biochemical roles 2.1 Neurotransmitter 3 Sources 3.1 Dietary Sources 3.2 Chemical Synthesis 4 References 5 See also 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, HO2CCHNH2CH2CHO.2 Asparagine is derived from aspartic acid via transamidation: HO2CCHNH2CH2CO2H + GCONH2 HO2CCHNH2CH2CONH2 + GCOOH where GCONH2 and GCOOH are glutamine and glutamic acid, respectively 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. 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, leads to endurance, although the evidence to support this idea is not strong.citation needed Sources Dietary Sources 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: luncheon meats, sausage meat, wild game Vegetable sources: sprouting seeds, oat flakes, avocado, asparagus. Chemical Synthesis Racemic aspartic acid can be synthesized from diethyl sodium phthalimidomalonate, C6H4CO2NCCO2Et2.4 References ^ 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. ^ Nelson, D. L.; Cox, M. M. Lehninger, Principles of Biochemistry 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6. ^ 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. ^ Dunn, M. S.; Smart, B. W. DL-Aspartic AcidOrganic Syntheses, Collected Volume 4, p.55 1963. http://www.orgsyn.org/orgsyn/pdfs/CV4P0055.pdf See also Aspartate transaminase Sodium polyaspartate, a synthetic polyamide v d e The 20 Common Amino Acids dp = data page Branched-chain amino acids Isoleucine dp | Leucine dp | Valine dp Non Branch-chain Alanine dp | Arginine dp | Asparagine dp | Aspartic acid dp | Cysteine dp | Glutamic acid dp | Glutamine dp | Glycine dp | Histidine dp | Lysine dp | Methionine dp | Phenylalanine dp | Proline dp | Serine dp | Threonine dp | Tryptophan dp | Tyrosine dp Other classifications Essential amino acids | Ketogenic amino acid | Glucogenic amino acid Major families of biochemicals Saccharides | Carbohydrates | Glycosides | | Amino acids | Peptides | Proteins | Glycoproteins | | Lipids | Terpenes | Steroids | Carotenoids Alkaloids | Nucleobases | Nucleic acids | | Enzyme cofactors | Flavonoids | Polyketides | Tetrapyrroles Retrieved from http://en..org/wiki/Aspartic_acid Categories: Proteinogenic amino acids | Glucogenic amino acids | Acidic amino acids | Dicarboxylic acids | NeurotransmittersHidden categories: All articles with statements | Articles with statements since March 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages বাংলা Català Česky Deutsch Español Esperanto Français Gaeilge í•œêµì–´ Bahasa Indonesia Italiano עברית LatvieÅ¡u Lëtzebuergesch Lietuvių Magyar Nederlands 日本語 Occitan Polski Português РуÑ?Ñ?кий Suomi Svenska Türkçe УкраїнÑ?ька ä¸æ–‡ This page was last modified on 9 September 2008, at 23:53
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