Arylmalonate Decarboxylase

Malonic acid ester synthesis is a classic but still one of the most important

C—C bond-forming reactions, because it is widely applicable to various types of compounds and the reaction can be performed under mild conditions without special care to remove the trace amount of water and oxygen contained in the solvent. This reaction is especially useful in the synthesis of carboxylic acids. One important class of carboxylic acids is arylpropionates because optically active ones are known to have anti-inflammatory activity and other interesting physiological

Flurbiprofen

Figure 8: Industrial process of the production of racemic flurbiprofen.

Flurbiprofen

Figure 8: Industrial process of the production of racemic flurbiprofen.

activities. These compounds are conveniently prepared via methylation of the corresponding arylmalonic esters followed by hydrolysis and decarboxylation. In fact, flurbiprofen is industrially produced according to this process (Fig. 8).6 However, the most serious drawback of this procedure is that it cannot be applied to the synthesis of optically active compounds.

Although there were some trials to prepare optically active carboxylic acids via asymmetric decarboxylation, the optical yields of the products were not high enough for practical use.7 Thus, it is strongly desirable to find an enzyme which catalyzes asymmetric decarboxylation of arylmethylmalonates to give optically pure arylpropionates.

Was this article helpful?

0 0

Post a comment