In this chapter, decarboxylation of disubstituted malonic acid derivatives and application of the transketolases in organic syntheses are summarized. Although decarboxylation may be seen as a simple C-C bond breaking reaction, it can be regarded as a carbanion-generating reaction. As the future directions of this field, expansion of some unique decarboxylation reactions is proposed. In relation of "carbanion" chemistry, promiscuity of enolase superfamily is also discussed in the chapter. Although decarboxylation reaction seems to be a simple one-carbon removing reaction, it is demonstrated that this reaction is a unique and useful reaction in the preparation of optically active carboxylic acids. In terms of the "carbanion equivalent," the enolase superfamily has a strong relation with decarboxylation reaction. In addition to natural promiscuity, one can change the enzyme to be promiscuous by introducing mutation, especially in the case of the enolase superfamily. This will be one of the challenging problems in future. For that purpose, biotechnology and informatics skill will be essential tool in addition to precise analysis of the reaction mechanism.
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