Nickel-catalyzed transamidation of aliphatic amide derivatives

Nickel-catalyzed transamidation of aliphatic amide derivatives.

Transamidation, or the conversion of one amide to another, is a long-standing challenge in organic synthesis. Although notable progress has been made in the transamidation of primary amides, the transamidation of secondary amides has remained underdeveloped, especially when considering aliphatic substrates. Herein, we report a two-step approach to achieve the transamidation of secondary aliphat...

Nickel-catalyzed transamidation of aliphatic amide derivatives† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc01980g

A two-step approach to achieve secondary amide transamidation enabled by nickel catalysis

A long-standing challenge in synthetic chemistry is the development of the transamidation reaction. This process, which involves the conversion of one amide to another, is typically plagued by unfavourable kinetic and thermodynamic factors. Although some advances have been made with regard to the transamidation of primary amide substrates, secondary amide transamidation has remained elusive. He...

Specificity of papain-catalyzed transamidation reactions.

In the experiments reported in the present communication, these studies have been extended with special reference to the specificity of the enzyme toward the dipeptide used as replacement agent. It had been suggested (1) that the value of pKz’ of a dipeptide is a determining factor in the efficiency with which it can participate in a transamidation reaction at ‘a given pH. This suggestion has b...

Transamidation reactions catalyzed by cathepsin C.

Previous publications from this laboratory (l-3) have described the catalysis of transamidation reactions by the proteinases papain, ficin, and crystalline chymotrypsin. In addition, preliminary experiments were reported on replacement reactions catalyzed by beef spleen cathepsin C, an intracellular endopeptidase of animal tissues, which resembles pancreatic chymotrypsin in its specificity. The...