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Citrate

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Chemical structure of citric acid.

A citrate is an ionic form of citric acid, such as C3H5O(COO)33−, that is, citric acid minus three hydrogen ions.

Citrates are compounds containing this group, either ionic compounds, the salts, or analogous covalent compounds, esters. An example of a salt is sodium citrate and an ester is trimethyl citrate. See category for a bigger list.

Since citric acid is a multifunctional acid, intermediate ions exist, hydrogen citrate ion, HC6H5O72− and dihydrogen citrate ion, H2C6H5O7. These may form salts as well, called acid salts.

Salts of the hydrogen citrate ions are weakly acidic, while salts of the citrate ion itself (with an inert cation such as sodium ion) are weakly basic.

Citrate is a key component in the commonly used SSC 20X hybridization buffer. There exists authoritative literature (Maniatis) that incorrectly instructs the preparation of this buffer to include 3M NaCl and 0.3M Sodium Citrate, to be titrated up with NaOH to a pH of 7. When the two components are actually mixed together, the pH is slightly basic. Therefore, the pH of the solution should instead be titrated down to 7 with HCl.

Contents

[edit] Metabolism

[edit] TCA cycle

Citrate is an intermediate in the TCA (Krebs) Cycle. After pyruvate dehydrogenase forms acetyl CoA, by oxidative decarboxylation with five cofactors(Thiamine pyrophosphate, lipoamide, FAD, NAD+, and CoA), citrate synthase catalyzes the condensation of OAA with Acetyl CoA to form citrate. The six-carbon molecules citrate are decarboxylated to be a four-carbon molecule, succinyl CoA. The oxaloacetate are regenerated afterwards in TCA cycle and it can be used to generate another citrate molecule.

See also TCA cycle

[edit] Role in Glycolysis

High concentration of citrate can inhibit phosphofructokinase, the pace-maker of glycolysis.

[edit] See also


 

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Citric Acid Cycle Metabolic Pathway
Oxaloacetate Malate Fumarate Succinate Succinyl CoA
Image:Oxaloacetate wpmp.png Image:S-malate wpmp.png Image:Fumarate wpmp.png Image:Succinate wpmp.png Image:Succinyl-CoA wpmp.png
Image:Biochem reaction arrow reverse NNYY horiz med.png Image:Biochem reaction arrow reverse NNYN horiz med.png Image:Biochem reaction arrow reverse NNYY horiz med.png Image:Biochem reaction arrow reverse NNYY horiz med.png
Acetyl CoA NADH + H+ NAD+ H2O FADH2 FAD CoA + ATP Pi + ADP
Image:Acetyl co-A wpmp.png + H2O Image:Biochem reaction arrow special 1.png Image:Biochem reaction arrow special 2.png NADH + H+ + CO2
CoA NAD+
Image:Citrate wpmp.png H2O Image:Cis-Aconitate wpmp.png H2O Image:Threo-Ds-isocitrate wpmp.png NADP+ NADPH + H+ Image:Oxalosuccinate wpmp.png CO2 Image:2-oxoglutarate wpmp.png
Image:Biochem reaction arrow foward NYNN horiz med.png Image:Biochem reaction arrow foward YNNN horiz med.png Image:Biochem reaction arrow foward YYNN horiz med.png Image:Biochem reaction arrow foward NYNN horiz med.png
Citrate cis-Aconitate Isocitrate Oxalosuccinate Alpha-ketoglutarate



Antithrombotics (thrombolytics, anticoagulants, and antiplatelet drugs) (B01) edit
Vitamin K antagonists:

Acenocoumarol, Clorindione, Dicumarol (Dicoumarol}, Diphenadione, Ethyl biscoumacetate, Phenprocoumon, Phenindione, Tioclomarol, Warfarin

Heparin group (Platelet
aggregation inhibitors):

Antithrombin III, Bemiparin, Dalteparin, Danaparoid, Enoxaparin, Heparin, Nadroparin, Parnaparin, Reviparin, Sulodexide, Tinzaparin

Other Platelet
aggregation inhibitors:

Abciximab, Acetylsalicylic acid (Aspirin), Aloxiprin, Beraprost, Ditazole, Carbasalate calcium, Cloricromen, Clopidogrel, Dipyridamole, Epoprostenol, Eptifibatide, Indobufen, Iloprost, Picotamide, Prasugrel, Ticlopidine, Tirofiban, Treprostinil, Triflusal

Enzymes:

Alteplase, Ancrod, Anistreplase, Brinase, Drotrecogin alfa, Fibrinolysin, Protein C, Reteplase, Saruplase, Streptokinase, Tenecteplase, Urokinase

Direct thrombin inhibitors:

Argatroban, Bivalirudin, Dabigatran, Desirudin, Hirudin, Lepirudin, Melagatran, Ximelagatran

Other antithrombotics:

Dabigatran, Defibrotide, Dermatan sulfate, Fondaparinux, Rivaroxaban

Non-medicinal:

Citrate, EDTA, Oxalate

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This article is of interest to the Metabolic Pathways WikiProject.

es:Citrato pl:Cytryniany pt:Citrato su:Sitrat

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