The goal of the project was to investigate a biological peculiarity--that all organisms use only the (L) configuration of amino acids to form proteins.  We aimed to discover if the pre-existing stereochemical configuration of an amino acid would select the configuration of its coupling partner in dipeptide formation.  Would (L) alanine prefer to couple with (L) alanine or (D) alanine?  The first step in this project is to master coupling reactions with amino acids.  Our approach was to utilize carboxyl group activation and amino group protection. Activation was achieved through esterification of the carboxyl group with thionyl chloride and alcohol (methanol, phenol, t-butanol).  The amino protection was accomplished via addition of a CBZ or t-Boc group or amidization of the amine with an acyl group. Products of reactions were analyzed with NMR spectroscopy.

On the origins of stereochemical selectivity in peptide synthesis: Determining why all organisms use L-amino acids to make proteins

239th National Meeting (2010)

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