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Under typical physiological conditions, acetoacetic acid exists as its conjugate base, acetoacetate: AcCH 2 CO 2 H → AcCH 2 CO − 2 + H + Unbound acetoacetate is primarily produced by liver mitochondria from its thioester with coenzyme A (CoA): AcCH 2 C(O)−CoA + OH − → AcCH 2 CO − 2 + H−CoA. The acetoacetate-CoA itself is formed by ...
Acetoacetic ester synthesis is a chemical reaction where ethyl acetoacetate is alkylated at the α-carbon to both carbonyl groups and then converted into a ketone, or more specifically an α-substituted acetone. This is very similar to malonic ester synthesis. Acetoacetic ester synthesis equation
Ketone bodies are water-soluble molecules or compounds that contain the ketone groups produced from fatty acids by the liver (ketogenesis). [1] [2] Ketone bodies are readily transported into tissues outside the liver, where they are converted into acetyl-CoA (acetyl-Coenzyme A) – which then enters the citric acid cycle (Krebs cycle) and is oxidized for energy.
β-Hydroxybutyrate, BHB, is also synthesized within liver cells; this is accomplished through the metabolism of fatty acids. Through a series of reactions, acetoacetate is first produced; and it is this acetoacetate that is reduced into β-hydroxybutyrate, catalyzed by the β-hydroxybutyrate dehydrogenase enzyme.
When 4-maleylacetoacetate isomerase is unable to function properly, the 4-maleylacetoacetate may be converted instead to succinylacetoacetate and further broken down into succinate and acetoacetate by fumarylacetoacetate hydrolase. [3] This image shows the pathway that 4-maleylacetoacetate follows when 4-maleylacetoacetate isomerase is not present.
The enzyme acetoacetyl-CoA hydrolase (EC 3.1.2.11) catalyzes the reaction . acetoacetyl-CoA + H 2 O CoA + acetoacetate. This enzyme belongs to the family of hydrolases, specifically those acting on thioester bonds.
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Using an external PC has some downsides. For example, external PCs typically complicate reaction design because the PC may react with both the bound and unbound substrate. If a reaction occurs between the unbound substrate and the PC, enantioselectivity is lost and other side reactions may occur.