aspartic acid

アスパラギン酸

WordNet

1. street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
2. any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
3. having the characteristics of an acid; "an acid reaction"

PrepTutorEJDIC

1. 酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/06/21 01:18:04」(JST)

wiki ja

[Wiki ja表示]

アスパラギン酸
IUPAC名 Trivial: Aspartic acid Systematic: 2-Aminobutanedioic acid
別称 Aminosuccinic acid, asparagic acid, asparaginic acid
識別情報
CAS登録番号	617-45-8 ,  56-84-8 (L-体) 1783-96-6 (D-体)
PubChem	424
ChemSpider	411
UNII	28XF4669EP
EINECS番号	200-291-6
KEGG	C00049
ChEMBL	CHEMBL139661
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)  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
特性
化学式	C4H7NO4
モル質量	133.1 g mol−1
特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

アスパラギン酸（アスパラギンさん、aspartic acid）とは、アミノ酸のひとつで、2-アミノブタン二酸のこと。示性式は HOOCCH₂CH(COOH)NH₂)。略号はD あるいは Asp。光学異性体としてL体とD体の両方が存在する。アスパラギンの加水分解物から単離され、由来とその構造からこの名がついた。

酸性極性側鎖アミノ酸に分類される。L体のアスパラギン酸は蛋白質を構成するアミノ酸のひとつ。非必須アミノ酸で、グリコーゲン生産性を持つ。うま味成分のひとつ。

致死量はLD₅₀=16g/kgである。

生合成

生体内では、クエン酸回路の一員であるオキサロ酢酸が、アスパラギン酸アミノトランスフェラーゼ (EC 2.6.1.1) によるグルタミン酸からのアミノ基の転移を受けて生合成される。

oxaloacetate + L-glutamate → L-aspartate + 2-oxoglutarate

工業生産

工業的にはフマル酸とアンモニアを原料として大腸菌由来のアスパルターゼを用いる。大腸菌はκ-カラギーナンで固定化され、バイオリアクターを用いて回分法で生産される。

物性

• 分子量 133.10
• 等電点 2.77
• 溶解性 水にやや難溶、エタノール・ジエチルエーテルに不溶。希塩酸・希硫酸に可溶。
• 溶解度（水、g/100g）0.42 (20℃)、0.85 (40℃)、1.70 (60℃)
• ファンデルワールス半径 91

神経伝達物質

アスパラギン酸は中枢神経系の興奮性神経伝達物質で、大脳皮質、小脳及び脊髄などに存在するNMDA受容体に対しアゴニストとして作用する。アミノ酸系の神経伝達物質は、アスパラギン酸に加えてグルタミン酸(Glu)、γ-アミノ酪酸(GABA)、グリシン(Gly)がある。

関連項目

リンゴ酸-アスパラギン酸シャトル

出典

外部リンク

• アスパラギン酸 - 「健康食品」の安全性・有効性情報 （国立健康・栄養研究所）

wiki en

[Wiki en表示]

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 Y 56-84-8 (L-isomer) N 1783-96-6 (D-isomer) N
ChEBI	CHEBI:22660 Y
ChEMBL	ChEMBL139661 Y
ChemSpider	411 Y
EC Number	200-291-6
Jmol 3D model	Interactive image Interactive image
KEGG	C16433 Y
PubChem	424
UNII	28XF4669EP Y
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
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
N verify (what is YN ?)
Infobox references

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, 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.

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. 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.

[[File:

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

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

File:WP534.png

Glycolysis and Gluconeogenesis edit

Neurotransmitter

Aspartate (the conjugate base of aspartic acid) stimulates NMDA receptors, though not as strongly as the amino acid neurotransmitter L-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: oysters, luncheon meats, sausage meat, wild game
• Vegetable sources: sprouting seeds, oat flakes, avocado, asparagus, young sugarcane, and molasses from sugar beets.
• 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).

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.

See also

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

References

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

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.

• 1. 糖尿病におけるインスリン療法の一般原則 general principles of insulin therapy in diabetes mellitus
• 2. 嚢胞性線維症：肝胆道系疾患 cystic fibrosis hepatobiliary disease
• 3. 成人における肝性脳症：治療 hepatic encephalopathy in adults treatment
• 4. Complementary and alternative treatments for anxiety symptoms and disorders: Herbs and medications
• 5. Management of chronic pain in chronic kidney disease

English Journal

• Detection of antibacterial activity of an enzymatic hydrolysate generated by processing rainbow trout by-products with trout pepsin.

• Wald M1, Schwarz K2, Rehbein H3, Bußmann B4, Beermann C5.
• Food chemistry.Food Chem.2016 Aug 15;205:221-8. doi: 10.1016/j.foodchem.2016.03.002. Epub 2016 Mar 2.
• Trout by-product hydrolysates, generated using trout pepsin, were characterized and studied in terms of their antibacterial effects against food contaminants and fish farming pathogens. After a hydrolysis time of 25min, the hydrolysates demonstrated inhibitory activity against several gram-positive
• PMID 27006234

• Effect of cooking methods on nutritional quality and volatile compounds of Chinese chestnut (Castanea mollissima Blume).

• Li Q1, Shi X1, Zhao Q1, Cui Y1, Ouyang J2, Xu F3.
• Food chemistry.Food Chem.2016 Jun 15;201:80-6. doi: 10.1016/j.foodchem.2016.01.068. Epub 2016 Jan 18.
• This study aimed to evaluate the effects of different cooking methods on the content of important nutrients and volatiles in the fruit of Chinese chestnut. The nutritional compounds, including starch, water-soluble protein, free amino acids, reducing sugar, sucrose, organic acids and total flavonoid
• PMID 26868551

• Novel heart valve prosthesis with self-endothelialization potential made of modified polyhedral oligomeric silsesquioxane-nanocomposite material.

• Ghanbari H1, Radenkovic D2, Marashi SM3, Parsno S4, Roohpour N5, Burriesci G6, Seifalian AM7.
• Biointerphases.Biointerphases.2016 Jun 13;11(2):029801. doi: 10.1116/1.4939036.
• In the cardiovascular system, the endothelial layer provides a natural antithrombogenic surface on the inner portion of the heart and associated vessels. For a synthetic material therefore, the ability to attract and retain endothelial or endothelial progenitor cells (EPCs), ultimately creating a si
• PMID 26763768

Japanese Journal

• Nuclear localization domains of GATA activator Gln3 are required for transcription of target genes through dephosphorylation in Saccharomyces cerevisiae(GENETICS, MOLECULAR BIOLOGY, AND GENE ENGINEERING)

• Journal of bioscience and bioengineering 120(2), 121-127, 2015-08
• NAID 110009978121

• Sarcopenia and aspartic acid magnesium

• The journal of physical fitness and sports medicine : JPFSM : official journal of the Japanese Society of Physical Fitness and Sports Medicine 4(3), 287-294, 2015-07
• NAID 40020547349

• New Optical Resolution Method for Racemic DL-Aspartic Acid by Crystallization in the Presence of d- or l-Asparagine as a Tailor-Made Additive

• JOURNAL OF CHEMICAL ENGINEERING OF JAPAN 48(11), 903-908, 2015
• NAID 130005110446

Related Links

• Aspartic acid: MedlinePlus Medical Encyclopedia

Aspartic acid is a nonessential amino acids. Amino acids are building blocks of proteins. "Nonessential" means that our bodies produce it even if we do not get this amino acid from the food we eat. Aspartic acid is also ...

• D-Aspartic Acid - Scientific Review on Usage, Dosage, Side ...

D-aspartic acid (D-AA) is an amino acid regulator of testosterone synthesis and may act on a stimulatory receptor (NMDA). D-AA shows promise in aiding male fertility. Healthy men supplementing D-AA experience only temporary ...

Related Pictures

---

★リンクテーブル★

リンク元	「アスパラギン酸」「aspartate」「magnesium aspartate」「L-aspartate」「potassium aspartate」
拡張検索	「N-methyl-D-aspartic acid」「L-aspartic acid」「D-aspartic acid」「isoaspartic acid」
関連記事	「aspartic」

「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

「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

「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

「N-methyl-D-aspartic acid」

　　[★] N-メチル-D-アスパラギン酸

NMDA型グルタミン酸受容体刺激薬

関

N-methyl-D-aspartate、N-methylaspartate、NMDA

「L-aspartic acid」

　　[★]

L-アスパラギン酸

関

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

「D-aspartic acid」

　　[★]

D-アスパラギン酸

関

D-aspartate

「isoaspartic acid」

　　[★]

イソアスパラギン酸

「aspartic」

　　[★]

• adj.

• アスパラギン酸の

関

Asp、aspartate、aspartic acid、D