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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]]

File:WP534.png

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]]

File:TCACycle WP78.png

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.
^ http://www.pearsonhighered.com/mathews/ch14/c14gc.htm
^ "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

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. 肝細胞障害を検出するための肝臓生化学検査 liver biochemical tests that detect injury to hepatocytes
2. 水溶性ビタミンの概要 overview of water soluble vitamins
3. 先天性代謝異常：分類 inborn errors of metabolism classification
4. 乳酸アシドーシスの原因 causes of lactic acidosis
5. 乳児および小児における低血糖症の原因 causes of hypoglycemia in infants and children

English Journal

Hematological, biochemical and enzymological responses in an Indian major carp Labeo rohita induced by sublethal concentration of waterborne selenite exposure.

Ramesh M1, Sankaran M1, Veera-Gowtham V1, Poopal RK2.Author information 1Unit of Toxicology, Department of Zoology, School of Life Sciences, Bharathiar University, Coimbatore 641046, Tamil Nadu, India.2Unit of Toxicology, Department of Zoology, School of Life Sciences, Bharathiar University, Coimbatore 641046, Tamil Nadu, India. Electronic address: poopalramakrishanan@ymail.com.AbstractSelenium (Se) pollution in aquatic ecosystem is an environmental issue throughout the world. Elevated concentrations of inorganic Se from agricultural and industrial processes may cause adverse biological effects in aquatic organisms such as fish. In the present study, Labeo rohita an Indian major carp were exposed to sublethal concentration of Se (sodium selenite) for 35days and certain hematological, biochemical and enzymological parameters were estimated. The median lethal concentration of waterborne sodium selenite (Na2SeO3) to L. rohita was found to be 23.89mgL(-1) for 96h. During sublethal (2.38mgL(-1)) treatment, hematological and biochemical parameters such as hemoglobin (Hb) (except 14th day), hematocrit (Hct), erythrocyte (RBC) count and protein levels were found to be decreased in Se treated fish whereas leucocyte (WBC) count and glucose level increased in Se treated fish throughout the study period. The enzymatic parameters such as glutamate oxaloacetate transaminase (GOT), glutamate pyruvate transaminase (GPT) and lactate dehydrogenase (LDH) activities were found to be increased in liver of Se treated fish L. rohita. A biphasic response was observed in the value of mean corpuscular volume (MCV), mean corpuscular hemoglobin (MCH) and mean corpuscular hemoglobin concentration (MCHC). The alterations of these parameters can be used as suitable biomarkers in monitoring of selenium in the aquatic environment and to protect aquatic life.
Chemico-biological interactions.Chem Biol Interact.2014 Jan 25;207:67-73. doi: 10.1016/j.cbi.2013.10.018. Epub 2013 Oct 30.
Selenium (Se) pollution in aquatic ecosystem is an environmental issue throughout the world. Elevated concentrations of inorganic Se from agricultural and industrial processes may cause adverse biological effects in aquatic organisms such as fish. In the present study, Labeo rohita an Indian major c
PMID 24183823

ALG1-CDG: A new case with early fatal outcome.

Rohlfing AK1, Rust S2, Reunert J1, Tirre M2, Du Chesne I1, Wemhoff S3, Meinhardt F3, Hartmann H4, Das AM4, Marquardt T5.Author information 1Universitätsklinikum Münster, Klinik und Poliklinik für Kinder- und Jugendmedizin-Allgemeine Pädiatrie, Münster, Germany.2Leibniz-Institut für Arterioskleroseforschung, Münster, Germany.3Institut für Molekulare Mikrobiologie und Biotechnologie, Münster, Germany.4Clinic for Pediatric Kidney, Liver Metabolic Diseases, Hannover Medical School, Hannover, Germany.5Universitätsklinikum Münster, Klinik und Poliklinik für Kinder- und Jugendmedizin-Allgemeine Pädiatrie, Münster, Germany. Electronic address: marquat@uni-muenster.de.AbstractCongenital disorders of glycosylation (CDG) are a growing group of inherited metabolic disorders where enzymatic defects in the formation or processing of glycolipids and/or glycoproteins lead to variety of different diseases. The deficiency of GDP-Man:GlcNAc2-PP-dolichol mannosyltransferase, encoded by the human ortholog of ALG1 from yeast, is known as ALG1-CDG (CDG-Ik). The phenotypical, molecular and biochemical analysis of a severely affected ALG1-CDG patient is the focus of this paper. The patient's main symptoms were feeding problems and diarrhea, profound hypoproteinemia with massive ascites, muscular hypertonia, seizures refractory to treatment, recurrent episodes of apnoea, cardiac and hepatic involvement and coagulation anomalies. Compound heterozygosity for the mutations c.1145T>C (M382T) and c.1312C>T (R438W) was detected in the patient's ALG1-coding sequence. In contrast to a previously reported speculation on R438W we confirmed both mutations as disease-causing in ALG1-CDG.
Gene.Gene.2014 Jan 25;534(2):345-51. doi: 10.1016/j.gene.2013.10.013. Epub 2013 Oct 21.
Congenital disorders of glycosylation (CDG) are a growing group of inherited metabolic disorders where enzymatic defects in the formation or processing of glycolipids and/or glycoproteins lead to variety of different diseases. The deficiency of GDP-Man:GlcNAc2-PP-dolichol mannosyltransferase, encode
PMID 24157261

Metabolic flux analysis of recombinant Pichia pastoris growing on different glycerol/methanol mixtures by iterative fitting of NMR-derived (13)C-labelling data from proteinogenic amino acids.

Jordà J, de Jesus SS, Peltier S, Ferrer P, Albiol J.Author information Departament d'Enginyeria Química, Escola d'Enginyeria, Universitat Autònoma de Barcelona, Bellaterra (Cerdanyola del Vallès), Spain.AbstractThe yeast Pichia pastoris has emerged as one of the most promising yeast cell factories for the production of heterologous proteins. The readily available genetic tools and the ease of high-cell density cultivations using methanol or glycerol/methanol mixtures are among the key factors for this development. Previous studies have shown that the use of mixed feeds of glycerol and methanol seem to alleviate the metabolic burden derived from protein production, allowing for higher specific and volumetric process productivities. However, initial studies of glycerol/methanol co-metabolism in P. pastoris by classical metabolic flux analyses using (13)C-derived Metabolic Flux Ratio (METAFoR) constraints were hampered by the reduced labelling information obtained when using C3:C1 substrate mixtures in relation to the conventional C6 substrate, that is, glucose. In this study, carbon flux distributions through the central metabolic pathways in glycerol/methanol co-assimilation conditions have been further characterised using biosynthetically directed fractional (13)C labelling. In particular, metabolic flux distributions were obtained under 3 different glycerol/methanol ratios and growth rates by iterative fitting of NMR-derived (13)C-labelling data from proteinogenic amino acids using the software tool (13)CFlux2. Specifically, cells were grown aerobically in chemostat cultures fed with 80:20, 60:40 and 40:60 (w:w) glycerol/methanol mixtures at two dilutions rates (0.05hour(-1) and 0.16hour(-1)), allowing to obtain additional data (biomass composition and extracellular fluxes) to complement pre-existing datasets. The performed (13)C-MFA reveals a significant redistribution of carbon fluxes in the central carbon metabolism as a result of the shift in the dilution rate, while the ratio of carbon sources has a lower impact on carbon flux distribution in cells growing at the same dilution rate. At low growth rate, the percentage of methanol directly dissimilated to CO2 ranges between 50% and 70%. At high growth rate the methanol is completely dissimilated to CO2 by the direct pathway, in the two conditions of highest methanol content.
New biotechnology.N Biotechnol.2014 Jan 25;31(1):120-32. doi: 10.1016/j.nbt.2013.06.007. Epub 2013 Jul 8.
The yeast Pichia pastoris has emerged as one of the most promising yeast cell factories for the production of heterologous proteins. The readily available genetic tools and the ease of high-cell density cultivations using methanol or glycerol/methanol mixtures are among the key factors for this deve
PMID 23845285

Japanese Journal

1P-147 オキサロ酢酸加水分解酵素遺伝子の高発現による糸状菌Aspergillus nigerを利用したシュウ酸の高収率生産(代謝工学,一般講演)

小林慶一,渡邉昭太郎,桐村光太郎
日本生物工学会大会講演要旨集 66, 54, 2014-08-05
NAID 110009906228

Cloning and expression analysis of a cDNA encoding an oxaloacetate acetylhydrolase from the brown-rot fungus Fomitopsis palustris

Hisamori Hiromichi,Watanabe Tomoki,Suzuki Shiro,Okawa Kumiko,Sakai Haruko,Yoshimura Tsuyoshi,Umezawa Toshiaki,Hattori Takefumi
Sustainable humanosphere : bulletin of Research Institute for Sustainable Humanosphere Kyoto University 9, 57-64, 2013-10-31
NAID 120005465826

Cisplatin Binding and Inactivation of Mitochondrial Glutamate Oxaloacetate Transaminase in Cisplatin-Induced Rat Nephrotoxicity

OZAKI Taku,ISHIGURO Sei-ichi,ITOH Hideaki,FURUHAMA Kazuhisa,NAKAZAWA Mitsuru,YAMASHITA Tetsuro
Bioscience, biotechnology, and biochemistry 77(8), 1645-1649, 2013-08-23
NAID 10031195811

Related Pictures

★リンクテーブル★

リンク元	「解糖系」「オキサロ酢酸」「ビオチン」「oxal」

「解糖系」

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 (Jmol)	Interactive image
ChEBI	CHEBI:30744
ChemSpider	945
ECHA InfoCard	100.005.755
EC Number	206-329-8
IUPHAR/BPS	5236
PubChem	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

　　[★]

英: glycolytic pathway
同: エムデン-マイヤーホフ経路 Embden-Meyerhof pathway
関: 解糖、TCA回路

CH(OH)-CH(OH)-C(OH)H-CH(OH)-C(CH2OH)H-O- グルコース (OHが↓↓↑↓↑)
CH(OH)-CH(OH)-C(OH)H-CH(OH)-C(CH2O-PO3)H-O- グルコース-6-リン酸 (OHが↓↓↑↓↑)
C(CH2OH)OH-C(OH)H-CH(OH)-C(CH2O-PO3)H-O- フルクトース-6-リン酸
C(CH2O-PO3)OH-C(OH)H-CH(OH)-C(CH2O-PO3)H-O- フルクトース-1,6-リン酸

glucose
↓-hexokinase/glucokinase(liver)
glucose 6-phosphate
↓-phosphohexose isomerase
fructose 6-phosphate
↓-phosphofructokinase
fructose 1,6-bisphosphate
↓-aldolase
glyceraldehyde 3-phosphate
↓-glyceraldehyde-3-phosphate dehydrogenase
1,3-bisphosphoglycerate
↓-phosphoglycerate kinase →ATP
3-phosphoglycerate
↓-phosphoglyceate mutase
2-phosphoglycerate
↓-enolase
phosphoenolpyruvate
↓-pyruvate kinase → ATP
pyruvate
　－(pyruvate dehydrogenase)→acetyl-CoA
　－(pyruvate carboxylase)→oxaloacetate－(NADH+H+)→malate

解糖系の酵素 (first aid step1 2006 p.87, FASTEP1_87_酵素一覧.xls)

1	galactokinase	キナーゼ
2	galactose-1-phosphate uridyltransferase	転移酵素
3	hexokinase/glucokinase	キナーゼ
4	glucose-6-phosphatase	ホスファターゼ
5	glucose-6-phosphate dehydrogenase	脱水素酵素
6	transketolase
7	phosphofructokinase	キナーゼ
8	fructose-1,6-bisphosphatase	ホスファターゼ
9	fructokinase	キナーゼ	フルクトキナーゼ
10	aldolase B		アルドラーゼ
11	pyruvate kinase	キナーゼ	ピルビン酸キナーゼ
12	pyruvate dehydrogenase	脱水素酵素	ピルビン酸デヒドロゲナーゼ
13	HMG-CoA reductase	還元酵素	HMG-CoA還元酵素
14	pyruvate carboxylase	カルボキシラーゼ	ピルビン酸カルボキシラーゼ
15	PEP carboxykinase	キナーゼ	PEPカルボキシキナーゼ
16	citrate synthase	合成酵素	クエン酸合成酵素
17	α-ketoglutarate dehydrogenase	脱水素酵素	α-ケトグルタミン酸脱水素酵素
18	ornithine transcarbamylase	転移酵素	オルニチンカルバモイルトランスフェラーゼ

「オキサロ酢酸」

　　[★]

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)

「ビオチン」

　　[★]

英: biotin
同: ビタミンB₇ vitamin B₇、補酵素R coenzyme R、ビタミンH vitamin H
関: ビタミン

機能

カルボキシラーゼの補酵素となり、CO₂キャリアーとして機能
体内で代謝されてビオチン酵素となり、炭素固定反応の補酵素となる。

1. pyruvate －(ピルビン酸カルボキシラーゼ)→ oxaloacetate

2. acetyl-CoA －(アセチルCoAカルボキシラーゼ)→ malonyl-CoA

3. proprionyl-CoA －(プロピオニルCoAカルボキシラーゼ)→ methylmalonyl-CoA　：奇数炭素脂肪酸の偶数炭素脂肪酸への変換、2-オキソ酪酸の代謝

臨床関連

ビオチン欠乏

dermatitis, enteritis. Caused by antibiotic use, ingestion of raw eggs. (FIRST AID step1 p.114)
アビジンと強固に結合する。卵白の過剰摂取によりビオチンの吸収が妨げられ欠乏症を生じうる。

「oxal」

　　[★]

comb form

シュウ酸の

HOOC-COOH

ex.

オキサロ酢酸 oxaloacetate

[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] ttp://www.pearsonhighered.com/mathews/ch14/c14gc.htm

[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
			Oxaloacetate			Malate			Fumarate			Succinate			Succinyl-CoA


Acetyl-CoA				NADH + H⁺	NAD⁺			H₂O		FADH₂	FAD		CoA + ATP(GTP)	P_i + ADP(GDP)
	+	H₂O														NADH + H⁺ + CO₂
		CoA														NAD⁺
					H₂O		H₂O			NAD(P)⁺	NAD(P)H + H⁺			CO₂


			Citrate			cis-Aconitate			Isocitrate			Oxalosuccinate			α-Ketoglutarate

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案内

oxaloacetate