アスパラギン酸カルシウム

関: calcium L-aspartate

WordNet

a white metallic element that burns with a brilliant light; the fifth most abundant element in the earths crust; an important component of most plants and animals (同)Ca, atomic number 20

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『カルシウム』(金属元素;化学記号は『Ca』)

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/01/02 05:50:41」(JST)

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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.

In proteins aspartate sidechains are often hydrogen bonded, often as asx turns or asx motifs, which often occur at the N-termini of alpha helices.

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 pK_a 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.

L-aspartic acid is one of the two main ingredients of the artificial sweetener aspartame, along with L-phenylalanine.

Discovery

Aspartic acid was first discovered in 1827 by Auguste-Arthur Plisson and Étienne Ossian Henry,^[3] derived from asparagine, which had been isolated from asparagus juice in 1806, by boiling with a base.^[4]

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.^[5] 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.

Metabolism

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.^[6] Asparagine is derived from aspartate via transamidation:

-O₂CCH(NH₂)CH₂CO₂- + GC(O)NH₃+ O₂CCH(NH₂)CH₂CONH₃+ + GC(O)O

(where GC(O)NH₂ and GC(O)OH 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. 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]}

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|{{{bSize}}}px|alt=Glycolysis and Gluconeogenesis edit]]

File:WP534.png

Glycolysis and Gluconeogenesis edit

^ The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534".

Neurotransmitter

Aspartate (the conjugate base of aspartic acid) stimulates NMDA receptors, though not as strongly as the amino acid neurotransmitter L-glutamate does.^[7]

Applications & Market

The global market for aspartic acid is $117MM annually (50-60K MT/Yr)^[8] with areas of growth accounting for an addressable market of $8.78BB.^[9] 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.

Superabsorbent polymers

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.^[9] 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.^[10] The polyaspartate market comprises a small fraction (est. < 1%) of the total SAP market.

Additional uses

In addition to SAP, aspartic acid has applications in the $19B fertilizer industry, where polyaspartate improves water retention and nitrogen uptake;^[11] the $1.1B (2020) concrete floor coatings market, where polyaspartic is a low VOC, low energy alternative to traditional epoxy resins;^[12] and lastly the >$5B scale and corrosion inhibitors market.^[13]

Aspartic acid is known to have a use in the synthesis of Lorglumide.

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: oysters, luncheon meats, sausage meat, wild game
Vegetable sources: sprouting seeds, oat flakes, avocado,^[14] asparagus,^[15] young sugarcane, and molasses from sugar beets.^[1]
Dietary supplements, either as aspartic acid itself or salts (such as magnesium aspartate)
The sweetener aspartame (brands: NutraSweet, Equal, Canderel, etc.)

Chemical synthesis

Racemic aspartic acid can be synthesized from diethyl sodium phthalimidomalonate, (C₆H₄(CO)₂NC(CO₂Et)₂).^[16]

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.

References

^ ^a ^b "862. Aspartic acid". The Merck Index (11th ed.). 1989. p. 132. ISBN 0-911910-28-X.
^ "ICSC 1439 - L-ASPARTIC ACID". inchem.org.
^ Berzelius, Jöns Jakob; Öngren, Olof Gustaf (1839). Traité de chimie (in French). 3. Brussels: A. Wahlen et Cie. p. 81. Retrieved 25 August 2015.
^ R.H.A. Plimmer (1912) [1908]. R.H.A. Plimmer & F.G. Hopkins, ed. The chemical composition of the proteins. Monographs on biochemistry. Part I. Analysis (2nd ed.). London: Longmans, Green and Co. p. 112. Retrieved January 18, 2010.
^ "Nomenclature and symbolism for amino acids and peptides (IUPAC-IUB Recommendations 1983)", Pure Appl. Chem., 56 (5): 595–624, 1984, doi:10.1351/pac198456050595 .
^ Lehninger, Albert L.; Nelson, David L.; Cox, Michael M. (2000), Principles of Biochemistry (3rd ed.), New York: W. H. Freeman, ISBN 1-57259-153-6 .
^ Chen, Philip E.; Geballe, Matthew T.; Stansfeld, Phillip J.; Johnston, Alexander R.; Yuan, Hongjie; Jacob, Amanda L.; Snyder, James P.; Traynelis, Stephen F.; Wyllie, David J. A. (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". Mol. Pharmacol. 67 (5): 1470–84. doi:10.1124/mol.104.008185. PMID 15703381.
^ Evans, J. in Commercial Amino Acids 101–103 (BCC Research, 2014).
^ ^a ^b Transparency Market Research. Superabsorbent polymers market - global industry analysis, size, share, growth, trends and forecase, 2014-2020. (2014).
^ Alford, D. D., Wheeler, A. P. & Pettigrew, C. A. Biodegradation of thermally synthesized polyaspartate. J Environ Polym Degr 2, 225–236 (1994).
^ Kelling, K. Crop Responses to Amisorb in the North Central Region. (University of Wisconsin-Madison, 2001).
^ Global concrete floor coatings market will be worth US$1.1 bn by 2020. Transparency Market Research (2015).
^ Corrosion inhibitors market analysis by product, by application, by end-use industry, and segment forecasts to 2020. Grand View Research (2014)
^ D. K. Salunkhe; S.S. Kadam (18 August 1995). Handbook of Fruit Science and Technology: Production, Composition, Storage, and Processing. CRC Press. pp. 368–. ISBN 978-0-8247-9643-3.
^ Douglas M. Considine (6 December 2012). Foods and Food Production Encyclopedia. Springer Science & Business Media. pp. 114–. ISBN 978-1-4684-8511-0.
^ Dunn, M. S.; Smart, B. W. (1950). "DL-Aspartic Acid". Org. Synth. 30: 7. ; Coll. Vol., 4, p. 55 .

External links

GMD MS Spectrum
American Chemical Society (21 April 2010). "Ancestral Eve' Crystal May Explain Origin of Life's Left-Handedness". ScienceDaily. Archived from the original on 23 April 2010. Retrieved 2010-04-21.

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English Journal

Endogenous aspartoacylase expression is responsive to glutamatergic activity in vitro and in vivo.

Francis JS, Strande L, Pu A, Leone P.SourceCell and Gene Therapy Center, UMDNJ School of Osteopathic Medicine, SC253, 2 Medical Centre Drive, Stratford, New Jersey. francijs@umdnj.edu.
Glia.Glia.2011 Oct;59(10):1435-46. doi: 10.1002/glia.21187. Epub 2011 May 23.
Aspartoacylase (ASPA) is an enzyme that functions to catabolize the neuronal amino acid derivative N-acetyl-L-aspartic acid (NAA). Loss of this function results in the failure of developmental myelination. NAA synthesis and catabolism are tightly compartmentalized within neurons and oligodendrocytes
PMID 21608034

Assessment of the cardiotoxicity of tulathromycin in rabbits.

Er A, Altan F, Cetin G, Dik B, Elmas M, Yazar E.SourceUniversity of Selcuk Department of Pharmacology and Toxicology, Faculty of Veterinary Medicine 42075 Campus, Konya Turkey.
Acta veterinaria Hungarica.Acta Vet Hung.2011 Sep;59(3):327-35.
The aim of this study was to determine the cardiotoxic potency of tulathromycin. Tulathromycin (10 mg/kg, SC) was administered to ten adult male rabbits, and blood samples were obtained before and after drug administration (0 and 6 hours). Serum cardiac damage markers (troponin I, creatine kinase-MB
PMID 21727065

Japanese Journal

Dopamine D_1 Agonist Facilitates Long‐term Depression Induction by Callosal Low‐frequency Stimulation in Rat Anterior Cingulate Cortex

Sakuragi Sokichi
愛知教育大学研究報告. 自然科学編 60, 63-69, 2011-03-01
… LFS-induced LTD was not blocked by application of the metabotropic glutamatergic receptor antagonist, MCPG or the voltage-gated calcium channel blocker, nifedipine, but was blocked by application of the N-methyl-D-aspartate receptor （NMDAR） antagonist, APV. …
NAID 80021880058

Pharmacological Study on Alzheimer’s Drugs Targeting Calcium/Calmodulin-Dependent Protein Kinase II

Moriguchi Shigeki
Journal of Pharmacological Sciences 117(1), 6-11, 2011
… N-Methyl-D-aspartate (NMDA)-evoked currents were recorded from rat cortical neurons in long-term cultured primary neurons using the whole-cell patch-clamp technique. … Furthermore, nefiracetam-induced LTP enhancement was closely associated with calcium/calmodulin-dependent protein kinase II (CaMKII) activation with concomitant increase in phosphorylation of AMPA-type glutamate receptor subunit 1 (GluA1) (Ser-831) as a postsynaptic CaMKII substrate. …
NAID 130001011760

Related Pictures

★リンクテーブル★

リンク元	「L-アスパラギン酸カルシウム」「calcium L-aspartate」
関連記事	「aspartate」「calcium」

「L-アスパラギン酸カルシウム」

Aspartic acid
Names
	IUPAC names Trivial: Aspartic acid; Systematic: 2-Aminobutanedioic acid
	Other names Aminosuccinic acid, asparagic acid, asparaginic acid
Identifiers
CAS Number	617-45-8 ; 56-84-8 (L-isomer) ; 1783-96-6 (D-isomer)
3D model (Jmol)	Interactive image; Interactive image
ChEBI	CHEBI:22660
ChEMBL	ChEMBL139661
ChemSpider	411
ECHA InfoCard	100.000.265
EC Number	200-291-6
KEGG	C16433
PubChem	424
UNII	28XF4669EP
	InChI InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9) Key: CKLJMWTZIZZHCS-UHFFFAOYSA-N ; InChI=1/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9) Key: CKLJMWTZIZZHCS-UHFFFAOYAE ;
	SMILES O=C(O)CC(N)C(=O)O ; C(C(C(=O)O)N)C(=O)O ;
Properties
Chemical formula	C4H7NO4
Molar mass	133.10 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
Acidity (pKa)	3.9
Magnetic susceptibility (χ)	-64.2·10−6 cm3/mol
Hazards
Safety data sheet	See: data page
NFPA 704	1 1 0
Supplementary data page
Structure and; properties	Refractive index (n),; Dielectric constant (εr), etc.
Thermodynamic; data	Phase behaviour; solid–liquid–gas
Spectral data	UV, IR, NMR, MS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

　　[★]

英: calcium L-aspartate
化: アスパラギン酸カルシウム calcium aspartate
商: L-アスパラギン酸Ca、アスパラ-CA、エルスプリーCA
関: カルシウム剤

「calcium L-aspartate」

　　[★]

L-アスパラギン酸カルシウム

関: calcium aspartate

「aspartate」

　　[★] アスパラギン酸、アスパラギン酸塩

関: Asp、aspartic、aspartic acid、D、L-aspartate、L-aspartic acid、magnesium aspartate、potassium aspartate; aspartic acid

「calcium」

　　[★]

カルシウム Ca2+

[WikiPathways-7] The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534".

[merck-1] "862. Aspartic acid". The Merck Index (11th ed.). 1989. p. 132. ISBN 0-911910-28-X.

[2] "ICSC 1439 - L-ASPARTIC ACID". inchem.org.

[3] Berzelius, Jöns Jakob; Öngren, Olof Gustaf (1839). Traité de chimie (in French). 3. Brussels: A. Wahlen et Cie. p. 81. Retrieved 25 August 2015.

[4] R.H.A. Plimmer (1912) [1908]. R.H.A. Plimmer & F.G. Hopkins, ed. The chemical composition of the proteins. Monographs on biochemistry. Part I. Analysis (2nd ed.). London: Longmans, Green and Co. p. 112. Retrieved January 18, 2010.

[IUPAC-5] "Nomenclature and symbolism for amino acids and peptides (IUPAC-IUB Recommendations 1983)", Pure Appl. Chem., 56 (5): 595–624, 1984, doi:10.1351/pac198456050595 .

[6] Lehninger, Albert L.; Nelson, David L.; Cox, Michael M. (2000), Principles of Biochemistry (3rd ed.), New York: W. H. Freeman, ISBN 1-57259-153-6 .

[8] Chen, Philip E.; Geballe, Matthew T.; Stansfeld, Phillip J.; Johnston, Alexander R.; Yuan, Hongjie; Jacob, Amanda L.; Snyder, James P.; Traynelis, Stephen F.; Wyllie, David J. A. (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". Mol. Pharmacol. 67 (5): 1470–84. doi:10.1124/mol.104.008185. PMID 15703381.

[9] Evans, J. in Commercial Amino Acids 101–103 (BCC Research, 2014).

[:0-10] Transparency Market Research. Superabsorbent polymers market - global industry analysis, size, share, growth, trends and forecase, 2014-2020. (2014).

[11] Alford, D. D., Wheeler, A. P. & Pettigrew, C. A. Biodegradation of thermally synthesized polyaspartate. J Environ Polym Degr 2, 225–236 (1994).

[12] Kelling, K. Crop Responses to Amisorb in the North Central Region. (University of Wisconsin-Madison, 2001).

[13] Global concrete floor coatings market will be worth US$1.1 bn by 2020. Transparency Market Research (2015).

[14] Corrosion inhibitors market analysis by product, by application, by end-use industry, and segment forecasts to 2020. Grand View Research (2014)

[SalunkheKadam1995-15] D. K. Salunkhe; S.S. Kadam (18 August 1995). Handbook of Fruit Science and Technology: Production, Composition, Storage, and Processing. CRC Press. pp. 368–. ISBN 978-0-8247-9643-3.

[Considine2012-16] Douglas M. Considine (6 December 2012). Foods and Food Production Encyclopedia. Springer Science & Business Media. pp. 114–. ISBN 978-1-4684-8511-0.

[17] Dunn, M. S.; Smart, B. W. (1950). "DL-Aspartic Acid". Org. Synth. 30: 7. ; Coll. Vol., 4, p. 55 .

v t e Neurotransmitters

Amino acid-derived	Major excitatory/inhibitory systems: Glutamate system: Agmatine Aspartic acid (aspartate) Cycloserine Glutamic acid (glutamate) Glutathione Glycine GSNO GSSG Kynurenic acid NAA NAAG Proline Serine; GABA system: GABA GABOB GHB; Glycine system: α-Alanine β-Alanine Glycine Hypotaurine Proline Sarcosine Serine Taurine; GHB system: GHB T-HCA (GHC) Biogenic amines: Monoamines: 6-OHM Dopamine Epinephrine (adrenaline) NAS (normelatonin) Norepinephrine (noradrenaline) Serotonin (5-HT); Trace amines: 3-Iodothyronamine N-Methylphenethylamine N-Methyltryptamine m-Octopamine p-Octopamine Phenylethanolamine Phenethylamine Synephrine Tryptamine m-Tyramine p-Tyramine; Others: Histamine Neuropeptides: See here instead.

Lipid-derived	Endocannabinoids: 2-AG 2-AGE (noladin ether) 2-ALPI 2-OG AA-5-HT Anandamide (AEA) DEA LPI NADA NAGly OEA Oleamide PEA RVD-Hpα SEA Virodhamine (O-AEA) Neurosteroids: See here instead.

Nucleobase-derived	Nucleosides: Adenosine system: Adenosine ADP AMP ATP

Vitamin-derived	Cholinergic system: Acetylcholine

Miscellaneous	Gasotransmitters: Carbon monoxide (CO) Hydrogen sulfide (H₂S) Nitric oxide (NO); Candidates: Acetaldehyde Ammonia (NH₃) Carbonyl sulfide (COS) Nitrous oxide (N₂O) Sulfur dioxide (SO₂)

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案内

calcium aspartate