Mechanism of decarboxylation of 1,3-dimethylorotic acid. A model for orotidine 5′-phosphate decarboxylase was written by Beak, Peter;Siegel, Brock. And the article was included in Journal of the American Chemical Society in 1976.Reference of 59864-31-2 This article mentions the following:
The decarboxylation of 1,3-dimethylorotic acid (I) is shown to proceed by sep. pH-determined pathways in sulfolane at 180-220°. Although a process involving ionization of I is the major pathway in the presence of excess base, decarboxylation is initiated by zwitterion formation in the neutral solvent. Measurements of the rate of loss of CO2 from 6-carboxy-2,4-dimethoxypyrimidine and 1-methyl-2,4-dimethoxypyrimidinium-6-carboxylate betaine (II) are used to estimate the equilibrium and rate constants for the zwitterionic pathway. Comparison of the rate constant for decarboxylation of II with kcat for orotidine 5′-phosphate decarboxylase shows that the biol. catalysis can be satisfactorily accounted for if the enzyme provides a site which displaces the equilibrium in favor of the zwitterionic form of orotidylic acid. It is also noted that the inhibitor, 6-azauridine monophosphate, which has a greater affinity for the enzyme than does the substrate, provides a partial model for the intermediate formed on loss of CO2 from the zwitterion. In the experiment, the researchers used many compounds, for example, 1-Methyl-6-oxo-1,6-dihydropyridine-2-carboxylic acid (cas: 59864-31-2Reference of 59864-31-2).
1-Methyl-6-oxo-1,6-dihydropyridine-2-carboxylic acid (cas: 59864-31-2) belongs to pyridine derivatives. Pyridine’s the lone pair does not contribute to the aromatic system but importantly influences the chemical properties of pyridine, as it easily supports bond formation via an electrophilic attack. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Reference of 59864-31-2