Oxidative decarboxylation

Oxidative decarboxylation reactions are oxidation reactions in which a carboxylate group is removed, forming carbon dioxide. They often occur in biological systems: there are many examples in the citric acid cycle. This type of reaction probably started early at the origin of life.[1]

Compared to Simple decarboxylation which belongs to Lyase group (EC class 4), Oxidative decarboxylation belongs to Oxidoreductase group (EC class 1).

Citric acid cycle

In the citric acid cycle pyruvate dehydrogenase, isocitrate dehydrogenase, and α-ketoglutarate dehydrogenase catalyze oxidative decarboxylation reactions. Each reaction reduces NAD⁺ to NADH and generates CO₂.[2]

Other occurrences

The transformation of glyoxylic acid to formic acid is also an oxidative decarboxylation. An example is the reaction of n-methalaniline with glyoxylic acid to form n-methyl-n-phenylformamide and formic acid, via decarboxylation of the glyoxylic acid.[3]

Reaction of n-methalaniline with glyoxylic acid

References

Leqraa, Naoual; Nicolet, Yvain; Milet, Anne; Vallée, Yannick (2 September 2020). "A way to thioacetate esters compatible with non-oxidative prebiotic conditions". Scientific Reports. Springer Science and Business Media LLC. 10 (1). doi:10.1038/s41598-020-71524-7. ISSN 2045-2322.
Voet, Donald; Voet, Judith; Pratt, Charlotte (2013). Fundamentals of Biochemistry (4 ed.). John Wiley and Sons. pp. 555–565. ISBN 9780470547847.
Lin, Dian-Zhao; Huang, Jing-Mei (20 March 2018). "Electrochemical N-Formylation of Amines via Decarboxylation of Glyoxylic Acid". Organic Letters. American Chemical Society (ACS). 20 (7): 2112–2115. doi:10.1021/acs.orglett.8b00698. ISSN 1523-7060.

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[Leqraa_Nicolet_Milet_Vallée-1] Leqraa, Naoual; Nicolet, Yvain; Milet, Anne; Vallée, Yannick (2 September 2020). "A way to thioacetate esters compatible with non-oxidative prebiotic conditions". Scientific Reports. Springer Science and Business Media LLC. 10 (1). doi:10.1038/s41598-020-71524-7. ISSN 2045-2322.

[2] Voet, Donald; Voet, Judith; Pratt, Charlotte (2013). Fundamentals of Biochemistry (4 ed.). John Wiley and Sons. pp. 555–565. ISBN 9780470547847.

[Lin_Huang_pp._2112–2115-3] Lin, Dian-Zhao; Huang, Jing-Mei (20 March 2018). "Electrochemical N-Formylation of Amines via Decarboxylation of Glyoxylic Acid". Organic Letters. American Chemical Society (ACS). 20 (7): 2112–2115. doi:10.1021/acs.orglett.8b00698. ISSN 1523-7060.