L-アスパラギン酸、L-アスパラギン酸塩

関: aspartate、aspartic acid、L-aspartic acid、magnesium aspartate、potassium aspartate

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the 12th letter of the Roman alphabet (同)l

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lira(イタリアの貨幣単位リラ)
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/01/18 16:17:51」(JST)

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Aspartic acid (abbreviated as Asp or D; encoded by the codons [GAU and GAC]) is an ɑ-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated -+NH3 form under biological conditions), an α-carboxylic acid group (which is in the deprotonated –COO- form under biological conditions), and a side chain CH₂COOH, classifying it as a charged(at physiological pH), aliphatic amino acid. It is semi-essential in humans, meaning the body can synthesize it from oxaloacetate.

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]

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,^[8] asparagus,^[9] 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).^[10]

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), 1984: 595–624, 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.
^ 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.

UpToDate Contents

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English Journal

Changes in total nitrogen and amino acid composition of New Zealand Undaria pinnatifida with growth, location and plant parts.

Zhou AY1, Robertson J2, Hamid N3, Ma Q1, Lu J4.
Food chemistry.Food Chem.2015 Nov 1;186:319-25. doi: 10.1016/j.foodchem.2014.06.016. Epub 2014 Jun 12.
Undaria pinnatifida is known as unwanted organism in New Zealand. However, Wakame is a traditional food made of U. pinnatifida, which is now cultured extensively in East Asia. Therefore, it is important to examine this introduced alga as a potential source of dietary protein for human consumption in
PMID 25976828

Variation in nutritional compositions, antioxidant activity and microstructure of Lycopus lucidus Turcz. root at different harvest times.

Lu YH1, Huang JH2, Li YC2, Ma TT3, Sang P2, Wang WJ2, Gao CY4.
Food chemistry.Food Chem.2015 Sep 15;183:91-100. doi: 10.1016/j.foodchem.2015.03.033. Epub 2015 Mar 17.
The objective of this study was to investigate the variation in nutritional compositions, antioxidant activity and microstructure of Lycopus lucidus Turcz. root at different harvest times. L. lucidus Turcz. roots, harvested from two sites (S1 and S2) at three different times (T1: 19-11-2013, T2: 22-
PMID 25863615

Formation and reduction of 5-hydroxymethylfurfural at frying temperature in model system as a function of amino acid and sugar composition.

Kavousi P1, Mirhosseini H2, Ghazali H3, Ariffin AA4.
Food chemistry.Food Chem.2015 Sep 1;182:164-70. doi: 10.1016/j.foodchem.2015.02.135. Epub 2015 Mar 5.
5-Hydroxymethylfurfural (HMF) is formed during heat treatment of carbohydrate-containing foods, especially in a deep-fat frying process. This study aimed to investigate the effect of amino acids on the formation and reduction of HMF from glucose, fructose and sucrose at frying temperature in model s
PMID 25842323

Japanese Journal

NAD+依存性L-アスパラギン酸脱水素酵素ホモログ遺伝子のクローニングと機能解析

米田一成,荒木朋洋
東海大学紀要. 農学部 37, 9-15, 2018-03-15
NAID 120006456016

Ｔｈｅ　Ｋｅｉｏ　Ｊｏｕｒｎａｌ　ｏｆ　Ｍｅｄｉｃｉｎｅ

Sasabe Jumpei,Suzuki Masataka
Ｔｈｅ　Ｋｅｉｏ　Ｊｏｕｒｎａｌ　ｏｆ　Ｍｅｄｉｃｉｎｅ 68(1), 1-16, 2018
… <p>Living organisms enantioselectively employ L-amino acids as the molecular architecture of protein synthesized in the ribosome. … Although L-amino acids are dominantly utilized in most biological processes, accumulating evidence points to the distinctive roles of D-amino acids in non-ribosomal physiology. … In contrast, archaea and eukaryotes are thought generally to synthesize only two kinds of D-amino acids: D-serine and D-aspartate. …
NAID 130007620380

Striatal N-Acetylaspartate Synthetase Shati/Nat8l Regulates Depression-Like Behaviors via mGluR3-Mediated Serotonergic Suppression in Mice

Miyamoto Yoshiaki,Iegaki Noriyuki,Fu equan,Ishikawa Yudai,Sumi Kazuyuki,Azuma Sota,Uno Kyosuke,Muramatsu Shin-ichi,Nitta Atsumi
International Journal of Neuropsychopharmacology 20(12), 1027-1035, 2017-08-31
… We have previously identified Shati/Nat8l, an N-acetyltransferase, in the brain using an animal model of psychosis. … Shati/Nat8l synthesizes N-acetylaspartate from L-aspartate and acetyl-coenzyme A. …
NAID 120006402036

「L-アスパラギン酸」

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)
ChEBI	CHEBI:22660
ChEMBL	ChEMBL139661
ChemSpider	411
EC Number	200-291-6
Jmol interactive 3D	Image; Image
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
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
	verify (what is ?)
	Infobox references

　　[★]

英: L-aspartic acid、L-aspartate
関: アスパラギン酸、アスパラギン酸カリウム、L-アスパラギン酸塩、アスパラギン酸マグネシウム
化: L-アスパラギン酸Ca、L-アスパラギン酸K、アスケート、アスパラ、アスパラ-CA、アスパラカリウム、アスパラギン酸カリウム、アスパラ配合、アミグランド、アルモカリン、エルスプリー、エルスプリーCA、ガスポート、ガモファー、トスフロキサシントシル酸塩、ファモチジン、プロテアミン12、プロテアミン12X、ユニカリック

「magnesium aspartate」

　　[★]

アスパラギン酸マグネシウム

関: aspartate、aspartic acid、L-aspartate、L-aspartic acid、magnesium L-aspartate、potassium aspartate

「potassium aspartate」

　　[★]

アスパラギン酸カリウム

関: aspartate、aspartic acid、L-aspartate、L-aspartic acid、magnesium aspartate

「L-aspartic acid」

　　[★]

L-アスパラギン酸

関: aspartate、aspartic acid、L-aspartate、magnesium aspartate、potassium aspartate

「L-アスパラギン酸塩」

　　[★]

英: L-aspartate
関: L-アスパラギン酸

「potassium L-aspartate and magnesium L-aspartate mixture」

　　[★] アスパラギン酸カリウム・アスパラギン酸マグネシウム合剤

「magnesium L-aspartate」

　　[★]

L-アスパラギン酸マグネシウム

関: magnesium aspartate

「calcium L-aspartate」

　　[★]

L-アスパラギン酸カルシウム

関: calcium aspartate

「potassium L-aspartate」

　　[★] L-アスパラギン酸カリウム

「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

「L」

　　[★]

[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), 1984: 595–624, 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.

[SalunkheKadam1995-9] 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.

[Considine2012-10] Douglas M. Considine (6 December 2012). Foods and Food Production Encyclopedia. Springer Science & Business Media. pp. 114–. ISBN 978-1-4684-8511-0.

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

リンク元	「L-アスパラギン酸」「magnesium aspartate」「potassium aspartate」「L-aspartic acid」「L-アスパラギン酸塩」
拡張検索	「potassium L-aspartate and magnesium L-aspartate mixture」「magnesium L-aspartate」「calcium L-aspartate」「potassium L-aspartate」
関連記事	「aspartate」「L」

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案内

L-aspartate