WordNet

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
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
having the characteristics of an acid; "an acid reaction"

PrepTutorEJDIC

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

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2018/06/13 19:00:44」(JST)

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Oxaloacetic acid (also known as oxalacetic acid) is a crystalline organic compound with the chemical formula HO₂CC(O)CH₂CO₂H. Oxaloacetic acid, in the form of its conjugate base oxaloacetate, is a metabolic intermediate in many processes that occur in animals. It takes part in the gluconeogenesis, urea cycle, glyoxylate cycle, amino acid synthesis, fatty acid synthesis and citric acid cycle.^[1]

Properties

Oxaloacetic acid undergoes successive deprotonations to give the dianion:

HO₂CC(O)CH₂CO₂H ⇌ ⁻O₂CC(O)CH₂CO₂H + H⁺ pK_a = 2.22

⁻O₂CC(O)CH₂CO₂H ⇌ ⁻O₂CC(O)CH₂CO₂⁻ + H⁺, pK_a = 3.89

At high pH, the enolizable proton is ionized:

⁻O₂CC(O)CH₂CO₂⁻ ⇌ ⁻O₂CC(O⁻)CHCO₂⁻ + H⁺, pK_a = 13.03

The enol forms of oxaloacetic acid are particularly stable, so much so that the two tautomer have different melting points (152 °C for the cis isoform and 184 °C for the trans isoform).

Biosynthesis

Oxaloacetate forms in several ways in nature. A principal route is upon oxidation of L-malate, catalysed by malate dehydrogenase, in the citric acid cycle. Malate is also oxidized by succinate dehydrogenase in a slow reaction with the initial product being enol-oxaloacetate.^[2]
It also arises from the condensation of pyruvate with carbonic acid, driven by the hydrolysis of ATP:

CH₃C(O)CO₂⁻ + HCO₃⁻ + ATP → ⁻O₂CCH₂C(O)CO₂⁻ + ADP + Pi

Occurring in the mesophyll of plants, this process proceeds via phosphoenolpyruvate, catalysed by pyruvate carboxylase.
Oxaloacetate can also arise from trans- or de- amination of aspartic acid.

Biochemical functions

Oxaloacetate is an intermediate of the citric acid cycle, where it reacts with acetyl-CoA to form citrate, catalysed by citrate synthase. It is also involved in gluconeogenesis, urea cycle, glyoxylate cycle, amino acid synthesis, and fatty acid synthesis. Oxaloacetate is also a potent inhibitor of Complex II.

Gluconeogenesis

Gluconeogenesis^[1] is a metabolic pathway consisting of a series of eleven enzyme-catalyzed reactions, resulting in the generation of glucose from non-carbohydrates substrates. The beginning of this process takes place in the mitochondrial matrix, where pyruvate molecules are found. A pyruvate molecule is carboxylated by a pyruvate carboxylase enzyme, activated by a molecule each of ATP and water. This reaction results in the formation of oxaloacetate. NADH reduces oxaloacetate to malate. This transformation is needed to transport the molecule out of the mitochondria. Once in the cytosol, malate is oxidized to oxaloacetate again using NAD+. Then oxaloacetate remains in the cytosol, where the rest of reactions will take place. Oxaloacetate is later decarboxylated and phosphorylated by phosphoenolpyruvate carboxykinase and becomes 2-phosphoenolpyruvate using guanosine triphosphate (GTP) as phosphate source. Glucose is obtained after further downstream processing.

Urea cycle

The urea cycle is a metabolic pathway that results in the formation of urea using two ammonium molecules and one bicarbonate molecule.^[1] This route commonly occurs in hepatocytes. The reactions related to the urea cycle produce NADH), and NADH can be produced in two different ways. One of these uses oxaloacetate. In the cytosol there are fumarate molecules. Fumarate can be transformed into malate by the actions of the enzyme fumarase. Malate is acted on by malate dehydrogenase to become oxaloacetate, producing a molecule of NADH. After that, oxaloacetate will be recycled to aspartate, as transaminases prefer these keto acids over the others. This recycling maintains the flow of nitrogen into the cell.

Relationship of oxaloacetic acid, malic acid, and aspartic acid

Glyoxylate cycle

The glyoxylate cycle is a variant of the citric acid cycle.^[3] It is an anabolic pathway occurring in plants and bacteria utilizing the enzymes isocitrate lyase and malate synthase. Some intermediate steps of the cycle are slightly different from the citric acid cycle; nevertheless oxaloacetate has the same function in both processes.^[1] This means that oxaloacetate in this cycle also acts as the primary reactant and final product. In fact the oxaloacetate is a net product of the glyoxylate cycle because its loop of the cycle incorporates two molecules of acetyl-CoA.

Fatty acid synthesis

In previous stages acetyl-CoA is transferred from the mitochondria to the cytoplasm where fatty acid synthase resides. The acetyl-CoA is transported as a citrate, which has been previously formed in the mitochondrial matrix from acetyl-coA and oxaloacetate. This reaction usually initiates the citric acid cycle, but when there is no need of energy it is transported to the cytoplasm where it is broken down to cytoplasmatic acetyl -CoA and oxaloacetate.

Another part of the cycle requires NADPH for the synthesis of fatty acids.^[4] Part of this reducing power is generated when the cytosolic oxaloacetate is returned to the mitochondria as long as the internal mitochondrial layer is non-permeable for oxaloacetate. Firstly the oxaloacetate is reduced to malate using NADH. Then the malate is decarboxylated to pyruvate. Now this pyruvate can easily enter the mitochondria, where it is carboxylated again to oxaloacetate by pyruvate carboxylase. In this way, the transfer of acetyl-CoA that is from the mitochondria to the outside of the cell into the cytoplasm produces a molecule of NADH. The overall reaction, which is spontaneous, may be summarized as:

HCO₃⁻ + ATP + acetyl-CoA → ADP + Pi + malonyl-CoA

Amino acid synthesis

Six essential amino acids and three nonessential are synthesized from oxaloacetate and pyruvate.^[5] Aspartate and alanine are formed from oxaloacetate and pyruvate, respectively, by transamination from glutamate. Asparagine, methionine, lysine and threonine are synthesized by aspartate, therefore given importance to oxaloacetate as without it, no aspartate would be formed and the following other amino acids would neither be produced.

Oxalate biosynthesis

Oxaloacetate produces oxalate by hydrolysis.^[6]

oxaloacetate + H₂O ⇌ oxalate + acetate

This process is catalyzed by the enzyme oxaloacetase.

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]]

Glycolysis and Gluconeogenesis edit

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

Click on genes, proteins and metabolites below to link to respective articles. ^{[§ 1]}

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|{{{bSize}}}px|alt=TCA Cycle edit]]

TCA Cycle edit

^ The interactive pathway map can be edited at WikiPathways: "TCACycle_WP78".

References

^ ^a ^b ^c ^d Nelson, David L.; Cox, Michael M. (2005), Principles of Biochemistry (4th ed.), New York: W. H. Freeman, ISBN 0-7167-4339-6
^ M.V. Panchenko; A.D. Vinogradov (1991). "Direct demonstration of enol-oxaloacetate as an immediate product of malate oxidation by the mammalian succinate dehydrogenase". FEBS Letters. 286 (1-2): 76–78. doi:10.1016/0014-5793(91)80944-X.
^ "Welcome to The Chemistry Place". www.pearsonhighered.com. Retrieved 5 April 2018.
^ "fatty acids synthesis". http://www.rpi.edu/dept/bcbp/molbiochem/MBWeb/mb2/part1/fasynthesis.htm. External link in |publisher= (help); Missing or empty |url= (help)
^ "http://faculty.ksu.edu.sa/69436/Documents/lecture-15-aa_from_oxaloacetate_and_pyruvate.pptx". External link in |title= (help)
^ Gadd, Geoffrey M. "Fungal production of citric and oxalic acid: importance in metal speciation, physiology and biogeochemical processes" Advances in Microbial Physiology (1999), 41, 47-92.

UpToDate Contents

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PMID 26499439

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Neuroscience letters.Neurosci Lett.2015 Oct 8;606:188-93. doi: 10.1016/j.neulet.2015.09.001. Epub 2015 Sep 3.
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Divergent biochemical and enzymatic properties of oxalate oxidase isoforms encoded by four similar genes in rice.

Li XC1, Liao YY1, Leung DW2, Wang HY1, Chen BL1, Peng XX1, Liu EE3.
Phytochemistry.Phytochemistry.2015 Oct;118:216-23. doi: 10.1016/j.phytochem.2015.08.019. Epub 2015 Sep 4.
The biochemical and enzymatic properties of four highly similar rice oxalate oxidase proteins (OsOxO1-4) were compared after their purification from the leaves of transgenic plants each overexpressing the respective OsOxO1-4 genes. Although alignment of their amino acid sequences has revealed diverg
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Journal of bioscience and bioengineering 121(2), 172-177, 2016-02
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「オキサロ酢酸」

Oxaloacetic acid
Names
	IUPAC name Oxobutanedioic acid
	Other names Oxaloacetic acid; Oxalacetic acid; 2-Oxosuccinic acid; Ketosuccinic acid
Identifiers
CAS Number	328-42-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:30744 ;
ChemSpider	945 ;
ECHA InfoCard	100.005.755
EC Number	206-329-8
IUPHAR/BPS	5236;
PubChem CID	970;
	InChI InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9) Key: KHPXUQMNIQBQEV-UHFFFAOYSA-N ;
	SMILES O=C(O)C(=O)CC(=O)O ;
Properties
Chemical formula	C4H4O5
Molar mass	132.07 g/mol
Density	0,18 g/cm3
Melting point	161 °C (322 °F; 434 K)
Thermochemistry
Std enthalpy of; formation (ΔfHo298)	-943.21 kJ/mol
Std enthalpy of; combustion (ΔcHo298)	-1205.58 kJ/mol
	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

　　[★]

oxal
英: oxaloacetate, oxaloacetic acid, OAA
関: TCA回路

命名

オキサロ oxal- は「シュウ酸の」という接頭辞。HOOC-CO-(シュウ酸の部分) + -CH₂-COOH(酢酸の部分)ということで命名されたと思われる。

構造

HOOC-CO-CH₂-COOH

機能

1. 糖新生の中間代謝産物：ミトコンドリアで起こる

ピルビン酸からオキサロ酢酸へ

CH₃-CO-COO^- + ATP + CO₂　－(ピルビン酸カルボキシラーゼ)→　HOOC-CO-CH₂-COOH + Pi

オキサロ酢酸からホスホエノールピルビン酸へ

HOOC-CO-CH₂-COOH + GTP　－(PEPカルボキシキナーゼ)→　CH2=C(OPO320)-CO-OH + GDP + CO2

オキサロ酢酸が脱炭酸されると共鳴安定化したエノレート陰イオンが生じ、その酸素がGTPのγリン酸基を攻撃してPEPとGDPができる(FB.308)

2. クエン酸回路の代謝産物：ミトコンドリアで怒る

マレイン酸 + NAD⁺ －(malate dehydrogenase)→　オキサロ酢酸 + NADH + H⁺

オキサロ酢酸 + アセチルCoA　－(citrate synthase)→　クエン酸 + HS-CoA

糖新生

グルコースの材料となるが、オキサロ酢酸はミトコンドリア内なので、いったんリンゴ酸かアスパラギン酸に変換して細胞質に輸送される (FB.328)

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

[WikiPathways-8] The interactive pathway map can be edited at WikiPathways: "TCACycle_WP78".

[Lehn-1] Nelson, David L.; Cox, Michael M. (2005), Principles of Biochemistry (4th ed.), New York: W. H. Freeman, ISBN 0-7167-4339-6

[2] M.V. Panchenko; A.D. Vinogradov (1991). "Direct demonstration of enol-oxaloacetate as an immediate product of malate oxidation by the mammalian succinate dehydrogenase". FEBS Letters. 286 (1-2): 76–78. doi:10.1016/0014-5793(91)80944-X.

[3] "Welcome to The Chemistry Place". www.pearsonhighered.com. Retrieved 5 April 2018.

[4] "fatty acids synthesis". http://www.rpi.edu/dept/bcbp/molbiochem/MBWeb/mb2/part1/fasynthesis.htm. External link in |publisher= (help); Missing or empty |url= (help)

[5] "http://faculty.ksu.edu.sa/69436/Documents/lecture-15-aa_from_oxaloacetate_and_pyruvate.pptx". External link in |title= (help)

[6] Gadd, Geoffrey M. "Fungal production of citric and oxalic acid: importance in metal speciation, physiology and biogeochemical processes" Advances in Microbial Physiology (1999), 41, 47-92.

v t e Citric acid cycle metabolic pathway
Acetyl-CoA + H₂O	Oxaloacetate NADH +H⁺ NAD⁺ Malate H₂O Fumarate FADH₂ FAD Succinate CoA + ATP (GTP) P_i + ADP (GDP) Succinyl-CoA
Acetyl-CoA + H₂O		NADH + H⁺ + CO₂
CoA		NAD⁺
	Citrate H₂O cis-Aconitate H₂O Isocitrate NAD(P)⁺ NAD(P)H + H⁺ Oxalosuccinate CO₂ 2-oxoglutarate

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案内

案内

oxaloacetic acid