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

WordNet

1. the 4th letter of the Roman alphabet (同)d

PrepTutorEJDIC

1. deuteriumの化学記号

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/06/23 20:51:39」(JST)

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Aspartic acid
IUPAC name Trivial: Aspartic acid Systematic: 2-Aminobutanedioic acid
Other names Aminosuccinic acid, asparagic acid, asparaginic acid
Identifiers
CAS number	617-45-8 Y,  56-84-8 (L-isomer) 1783-96-6 (D-isomer)
PubChem	424
ChemSpider	411 Y
UNII	28XF4669EP Y
EC-number	200-291-6
KEGG	C16433 Y
ChEBI	CHEBI:22660 Y
ChEMBL	CHEMBL139661 Y
Jmol-3D images	Image 1 Image 2
SMILES O=C(O)CC(N)C(=O)O C(C(C(=O)O)N)C(=O)O
InChI InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9) Y Key: CKLJMWTZIZZHCS-UHFFFAOYSA-N Y InChI=1/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9) Key: CKLJMWTZIZZHCS-UHFFFAOYAE
Properties
Molecular formula	C4H7NO4
Molar mass	133.10 g mol−1
Appearance	colourless crystals
Density	1.7 g/cm3
Melting point	270°C
Boiling point	324°C (decomposes)
Solubility in water	4.5 g/L
Acidity (pKa)	3.9
Hazards
MSDS	External MSDS
EU Index	not listed
NFPA 704	1 1 0
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Aspartic acid (abbreviated as Asp or D) is an α-amino acid with the chemical formula HOOCCH(NH₂)CH₂COOH. The carboxylate anion, salt, or ester 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 pK_a of 3.9, however in a peptide the pK_a is highly dependent on the local environment. A pK_a as high as 14 is not at all uncommon. Aspartate is pervasive in biosynthesis. As with all amino acids, the presence of acid protons depends on the residue's local chemical environment and the pH of the solution.

Discovery

Aspartic acid was first discovered in 1827 by Plisson, derived from asparagine, which had been isolated from asparagus juice in 1806, by boiling with a base.

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. 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.

Role in biosynthesis of amino acids

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. 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.

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Glycolysis and Gluconeogenesis edit

Neurotransmitter

Aspartate (the conjugate base of aspartic acid) stimulates NMDA receptors, though not as strongly as the amino acid neurotransmitter glutamate does.

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^{[citation needed]}, young sugarcane, and molasses from sugar beets.
• Dietary supplements, either as aspartic acid itself or salts (such as magnesium aspartate)
• The sweetener aspartame (NutraSweet, Equal, Canderel, etc.)

Chemical synthesis

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

The major disadvantage of the above technique is that equimolar amounts of each enantiomer are made, but the body only utilizes L-amino acids. Using biotechnology it is now possible to use immobilised enzymes to create just one type of enantiomer owing to their stereospecificity. Aspartic acid is made synthetically using ammonium fumarate and aspartase from E.coli, E.coli usually breaks down the aspartic acid as a nitrogen source but using excess amounts of ammonium fumarate a reversal of the enzyme's job is possible, and so aspartic acid is made to very high yields, 98.7 mM from 1 M.

See also

• Aspartate transaminase
• Polyaspartic acid
• Sodium poly(aspartate), a synthetic polyamide

References

External links

• 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

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

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English Journal

• Mice heterozygous for cathepsin D deficiency exhibit mania-related behavior and stress-induced depression.

• Zhou R1, Lu Y1, Han Y1, Li X1, Lou H1, Zhu L1, Zhen X2, Duan S3.
• Progress in neuro-psychopharmacology & biological psychiatry.Prog Neuropsychopharmacol Biol Psychiatry.2015 Dec 3;63:110-8. doi: 10.1016/j.pnpbp.2015.06.007. Epub 2015 Jun 16.
• Mutations in cathepsin D (CTSD), an aspartic protease in the endosomal-lysosomal system, underlie congenital neuronal ceroid-lipofuscinosis (cNCL, also known as CLN10), a devastating neurodegenerative disease. CLN10 patients die within the first few days of life, and in the few patients who live int
• PMID 26092248

• The hippocampal NMDA receptors may be involved in acquisition, but not expression of ACPA-induced place preference.

• Nasehi M1, Sharaf-Dolgari E2, Ebrahimi-Ghiri M3, Zarrindast MR4.
• Progress in neuro-psychopharmacology & biological psychiatry.Prog Neuropsychopharmacol Biol Psychiatry.2015 Dec 3;63:83-90. doi: 10.1016/j.pnpbp.2015.06.004. Epub 2015 Jun 11.
• Numerous studies have investigated the functional interactions between the endocannabinoid and glutamate systems in the hippocampus. The present study was made to test whether N-methyl-D-aspartate (NMDA) receptors of the CA1 region of the dorsal hippocampus (CA1) are implicated in ACPA (a selective
• PMID 26072736

• Amino acid-catalyzed formation of 2-vinylfuran from lipid-derived 4-oxo-2-hexenal.

• Zeng Z1, Ma J1, Liu B1, Jiang H2.
• Food chemistry.Food Chem.2015 Dec 1;188:591-5. doi: 10.1016/j.foodchem.2015.05.058. Epub 2015 May 14.
• The formation of 2-vinylfuran from the corresponding 4-oxo-2-hexenal (OHE, a lipid oxidation product) under the catalysis of amino acid were studied. The effects of amino acids, reaction temperature, reaction time, water content, pH, metallic ions and some food additives on the formation of 2-vinylf
• PMID 26041235

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 120002954861

• サプリメントとしてのD-アスパラギン酸

• 加藤 志郎,吉村 徹
• ビタミン 85(1), 29-30, 2011-01-25
• NAID 110008440796

Related Links

• Aspartic acid - Wikipedia, the free encyclopedia

The carboxylate anion, salt, or ester of aspartic acid is known as aspartate. The L-isomer of aspartate is one of the 20 ... Aspartate is pervasive in biosynthesis. As with all amino acids, the presence of acid protons depends on the ...

Related Pictures

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★リンクテーブル★

リンク元	「オルニチン回路」「アスパラギン酸」「magnesium aspartate」「L-aspartate」「potassium aspartate」
拡張検索	「D-aspartate oxidase」「aspartate-tRNA ligase」「non-N-methyl-D-aspartate receptor」「aspartate-ammonia ligase」「potassium L-aspartate」

「オルニチン回路」

　　[★]

英

ornithine cycle

同

尿素サイクル 尿素回路 urea cycle、クレブス-ヘンゼライト回路 Krebs-Henseleit cycle、オルニチンサイクル

関

オルニチン、尿素

• オルニチン回路に含まれる分子はアミノ酸である：アミノ基とカルボン酸を両方持つもの
• 最終産物である尿素の窒素は、アンモニアとアスパラギン酸に由来する

ミトコンドリア内の反応

1) アンモニア + 炭酸 + 2ATP → ADP + Pi + カルバモイルリン酸 
　　　　　　　　　　　　5)から
　　　　　　　　　　　　↓
2) カルバモイルリン酸 + オルニチン → シトルリン + Pi 
　　　　　　　　　　　　　　　　　　　↓
　　　　　　　　　　　　　　　　　　　3)へ

サイトソルの反応

　　2)から
　　↓
3) シトルリン + アスパラギン酸 + ATP → AMP + ピロリン酸 + アルギニノコハク酸 
4) アルギニノコハク酸 → フマル酸 + アルギニン 
5) アルギニン + 水 → 尿素 + オルニチン 
　　　　　　　　　　　　　　　↓
　　　　　　　　　　　　　　　2)へ

|
ornithine
|
----------mitochondria
|
ornithine
|
|<-carbamoyl phosphate {ornithine transcarbamoylase}
|
citrulline
|
----------mitochondria
|
citrulline
|
|<-aspartate {argininosuccinate synthase}
|
argininosuccinate
| 
|->fumarate {argininosuccinase}
|
arginine
|
|<-H2O
|           {arginase}
|->urea
|
ornithine
|

臨床関連

• 尿素サイクル異常症

「アスパラギン酸」

　　[★]

英

aspartate, aspartic acid, Asp, D

同

2-アミノコハク酸 2-aminosuccinic acid

化

アスパラギン酸カリウム potassium aspartate、アスパラギン酸マグネシウム

関

アミノ酸。L-アスパラギン酸

• 極性。酸性。
• カルボキシル基(carboxyl group)を有する。
• アラニンの側鎖にカルボキシル基が付いた形をしている。
• 側鎖：

-CH2-COOH

「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

「L-aspartate」

　　[★]

• 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

「potassium aspartate」

　　[★]

• アスパラギン酸カリウム

関

aspartate、aspartic acid、L-aspartate、L-aspartic acid、magnesium aspartate

「D-aspartate oxidase」

　　[★]

• D-アスパラギン酸酸化酵素、D-アスパラギン酸オキシダーゼ

「aspartate-tRNA ligase」

　　[★]

アスパラギン酸tRNAリガーゼ

関

aspartyl-tRNA synthetase

「non-N-methyl-D-aspartate receptor」

　　[★] 非NMDA受容体。非-N-メチル-D-アスパラギン酸受容体

「aspartate-ammonia ligase」

　　[★]

アスパラギン酸アンモニアリガーゼ

「potassium L-aspartate」

　　[★] L-アスパラギン酸カリウム