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Details of Aspartic acid
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A non-essential amino acid in protein. The body produces aspartic acid to form part of a liver enzyme that builds and breaks down proteins and amino acids, and detoxifies nitrogen in urea. Aspartic acid is a neurotransmitter. Details... Aspartic acid (abbreviated as Asp or D; Asx or B represent either aspartic acid or asparagine)[1] is an α-amino acid with the chemical formula HO2CCH(NH2)CH2CO2H. The L-isomer is a protonated varient of one of the 20 proteinogenic amino acids, i.e. the building blocks of proteins. Its codons are GAU and GAC. It is classified as an acidic amino acid, together with glutamic acid. Aspartic acid is pervasive in biosynthesis. 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," HO2CCH(NH2)CH2CHO.[2] Asparagine 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 and glutamic acid, respectively)
Other biochemical roles Aspartic acid 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 lead to endurance, although the evidence to support this idea is not strong.
Synthesis Racemic aspartic acid can be synthesized from diethyl sodium phthalimidomalonate, (C6H4(CO)2NC(CO2Et)2).[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 Acid"Organic Syntheses, Collected Volume 4, p.55 (1963). http://www.orgsyn.org/orgsyn/pdfs/CV4P0055.pdf
See also
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