Synthesis of the chiral pentadentate oxoferryl complex and its function in the enantioselective oxidation of peptides and the synthesis and characterization of the chiral cobalt(III) complex

Mirvat Hammoud, Wayne State University

Abstract

The development of a catalyst that enantioselectively attacks peptides derived from D-amino acids at a faster rate than those derived from L-amino acids is unknown. As previously mentioned, D-amino acids are the key components of the bacterial cell wall. Due to the fact that bacteria use D-amino acids in peptides, specifically in the peptidoglycan of their cell walls, and mammals do not, this methodology represents a potentially novel mode of action for antibiotics. R-CDPy3 complex was synthesized in order to mimic the activity of N4Py and especially Bn-TPEN (due to its structural similarity) in the cleavage of peptides. Two derivatives of the R-CDPy3 (R = Me, Et) ligand were prepared by inserting the methyl and ethyl groups instead of the benzyl which generate a less sterically hindered ligand. These two new ligands were successful in generating the Fe II and the Fe IV O complexes. These iron-based catalysts will be tested toward the oxidative cleavage of the backbone of amino acids and peptides. On the other hand, we have generated a new Co III complex derived from Bn-CDPy3. Interestingly, only one coordination geometry out of five possible modes of coordination was favored.

Recommended Citation

Mirvat Hammoud, "Synthesis of the chiral pentadentate oxoferryl complex and its function in the enantioselective oxidation of peptides and the synthesis and characterization of the chiral cobalt(III) complex" (January 1, 2009). ETD Collection for Wayne State University. Paper AAI1460040.
http://digitalcommons.wayne.edu/dissertations/AAI1460040