The way proteins perform various functions mostly depend on their size and the amino acids used as monomers for the protein formation. Unfortunately, nature did not provide many of different kinds of amino acids that would be incorporated in the protein synthesis. To address this issue chemical approach to biology has been much appreciated for quite some time. The most important approach to understand protein structure and function is to swap one of the natural amino acid with an unnatural at a specific site in a protein. These proteins can be further studied in bacteria, yeast or living cells for their behavior and activity. To provide a practical access to a number of structurally diverse amino acids, we describe a chemical synthesis strategy based on decarboxylative addition of keto acid to imines, which on further modifications would provide the expected amino acid in pure form. Also, the synthesis of new amino acids would provide unexpected acidity, nucleophilicity and hydrogen bonding potential that would help to selectively modify the protein for various biological applications.

Decarboxylative nucleophilic addition of keto acids to imines and ketones; Synthesis of unusual fluorine-containing amino acids

251st National Meeting (2016)

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