Date of Award
Doctor of Philosophy (PhD)
The chemical synthesis of highly specialized peptides that might possess catalytic action provides one of the approaches to an understanding of the mechanism of enzyme action. The experiments reported in this thesis involve the chemical synthesis of model compounds designed to explore how trypsin and chymotrypsin may function. Since several lines of evidence indicate a catalytic role for histidine residues in these enzymes, it was proposed to prepare imidazole derivatives with carefully designed side chains which might attract and orient similarly shaped substrates. A histidine with a lysine-like side chain attached to the imidazole ring was pro-posed as a model catalyst to mimic the specific action of trypsin, cyclo-D-Histidyl-L-phenylalanyl was proposed for a study of chymotrypsin-like activity. A third project concerned the determination of whether, in the reaction of 2-benzylimidazole with p-nitrophenyl phenylacetate, the two benzyl groups might attract each other and cause an increase in the rate of hydrolysis of the ester.
Hershey, John William Baker, "The Chemical Synthesis of Model Catalysts Related to Enzymes" (1963). Student Theses and Dissertations. 575.