Peptide Synthesis from D-Alanine

Current research indicates that peptides with hydrophobic and/or an overall positive charge usually have some antimicrobial activity. The goal of this CURE project is to synthesize peptides that are 2-3 amino acids long and are antimicrobial. When forming the desired peptide bond, protecting groups need to be used so that unwanted side-reactions with the free amino and carboxylic acid groups of each reactant don't occur. D-Alanine will have the amine group protected by a BOC group, leaving the carboxylic acid free to react. BOC-FF-OMe will have its BOC group removed and its carboxylic acid protected with an ester, leaving the amine group free to react. Both reactions will be monitored by TLC to determine if the product has formed. In the final reaction, the peptide bond will be formed using EDC as a coupling reagent. The protected amino acid products and the final peptide product will be analyzed by 1H NMR to determine the structure and purity. Additionally, any antimicrobial activity will be evaluated by growth inhibition assay using optical density measurement at 600 nm.