RC ( O ) CO 2 Fe II + O 2 ⟶ RCO 2 Fe IV = O + CO 2 {\displaystyle {\ce {RC(O)CO2Fe Decarboxylations are pervasive in biology. They are often classified according to the cofactors that catalyze the transformations. [7] Biotin-coupled processes effect the decarboxylation of malonyl-CoA to acetyl-CoA. Thiamine (T:) is the active component for decarboxylation of alpha-ketoacids, including pyruvate: T : + RC ( O ) CO 2 H ⟶ T = C ( OH ) R + CO 2 {\displaystyle {\ce {T\!:+\ RC(O)CO2H->T=C(OH)R{}+CO2}}} T = C ( OH ) R + R ′ COOH ⟶ T : + RC ( O ) CH ( OH ) R ′ {\displaystyle {\ce {T=C(OH)R{}+R'COOH->T\!:+\ RC(O)CH(OH)R'}}}

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Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO 2). Usually, decarboxylation refers to a reaction of carboxylic acids, removing a carbon atom from a carbon chain. The reverse process, which is the first chemical step in photosynthesis, is called carboxylation, the addition of CO 2 to a compound. Enzymes that catalyze decarboxylations are called decarboxylases or, the more formal term, carboxy-lyases ( EC number 4.1.1). The term "decarboxylation" usually means replacement of a carboxyl group ( −C(O)OH) with a hydrogen atom:Pyridoxal phosphate promotes decarboxylation of amino acids. Flavin-dependent decarboxylases are involved in transformations of cysteine. Iron-based hydroxylases operate by reductive activation of O 2 using the decarboxylation of alpha-ketoglutarate as an electron donor. The decarboxylation can be depicted as such: Hydrodecarboxylations involve the conversion of a carboxylic acid to the corresponding hydrocarbon. This is conceptually the same as the more general term "decarboxylation" as defined above except that it specifically requires that the carboxyl group is, as expected, replaced by a hydrogen. The reaction is especially common in conjunction with the malonic ester synthesis and Knoevenagel condensations. The reaction involves the conjugate base of the carboxyl group, a carboxylate ion, and an unsaturated receptor of electron density, such as a protonated carbonyl group. Where reactions entail heating the carboxylic acid with concentrated hydrochloric acid, such a direct route is impossible as it would produce protonated carbon dioxide. In these cases, the reaction is likely to occur by initial addition of water and a proton. [6] In biochemistry [ edit ]

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Decarboxylation is one of the oldest known organic reactions. It is one of the processes assumed to accompany pyrolysis and destructive distillation. Metal salts, especially copper compounds, [1] facilitate the reaction via the intermediacy of metal carboxylate complexes. Decarboxylation of aryl carboxylates can generate the equivalent of the corresponding aryl anion, which in turn can undergo cross coupling reactions. [2]Important exceptions are the decarboxylation of beta- keto acids, β,γ-unsaturated acids, and α-phenyl, α-nitro, and α-cyanoacids. Such reactions are accelerated due to the formation of a zwitterionic tautomer in which the carbonyl is protonated and the carboxyl group is deprotonated. [5] Named decarboxylation reactions [ edit ] Decarboxylation of alkanoic acids is often slow. Thus, typical fatty acids do not decarboxylate readily. Overall, the facility of decarboxylation depends upon stability of the carbanion intermediate R −