The Broad Aryl Acid Specificity of the Amide Bond Synthetase McbA Suggests Potential for the Biocatalytic Synthesis of Amides was written by Petchey, Mark;Cuetos, Anibal;Rowlinson, Benjamin;Dannevald, Stephanie;Frese, Amina;Sutton, Peter W.;Lovelock, Sarah;Lloyd, Richard C.;Fairlamb, Ian J. S.;Grogan, Gideon. And the article was included in Angewandte Chemie, International Edition in 2018.Application In Synthesis of 6-Acetylpicolinic acid This article mentions the following:
Amide bond formation is one of the most important reactions in pharmaceutical synthetic chem. The development of sustainable methods for amide bond formation, including those that are catalyzed by enzymes, is therefore of significant interest. The ATP-dependent amide bond synthetase (ABS) enzyme McbA, from Marinactinospora thermotolerans, catalyzes the formation of amides as part of the biosynthetic pathway towards the marinacarboline secondary metabolites. The reaction proceeds via an adenylate intermediate, with both adenylation and amidation steps catalyzed within one active site. In this study, McbA was applied to the synthesis of pharmaceutical-type amides from a range of aryl carboxylic acids with partner amines provided at 1-5 molar equivalents. The structure of McbA revealed the structural determinants of aryl acid substrate tolerance and differences in conformation associated with the two half reactions catalyzed. The catalytic performance of McbA, coupled with the structure, suggest that this and other ABS enzymes may be engineered for applications in the sustainable synthesis of pharmaceutically relevant (chiral) amides. In the experiment, the researchers used many compounds, for example, 6-Acetylpicolinic acid (cas: 122637-39-2Application In Synthesis of 6-Acetylpicolinic acid).
6-Acetylpicolinic acid (cas: 122637-39-2) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Application In Synthesis of 6-Acetylpicolinic acid