Synthesis of Se-Adenosyl-L-Selenohomocysteine Selenoxide and Potential Gram-Negative Antibacterial Analogs.

摘要

This paper includes work performed on two separate projects. The first project is the synthesis and characterization of a new analog of S-adenosylmethionine (AdoMet or SAM) called Se-adenosyl-L-selenohomocysteine selenoxide (SeAHO). This work outlines the total synthesis starting from adenosine and the characterization data collected along the way. This work culminated with the first successful synthesis of the desired selenoxide analog that can now be studied further for its potential biological activity. The second project involves medicinal chemistry efforts in synthesizing analogs of the oxazolidinone scaffold with desirable characteristics for potential treatment of Gram-negative bacterial infections. The oxazolidinone scaffold has already been shown to be successful in treating Gram-positive bacterial infections and the goal of our research is to be able to convert it to one that also has activity against Gram-negative bacteria. With the goal of developing a novel approach to making compounds with this activity, we look at specific modifications made to certain areas of the scaffold and how these changes impacted the activity against different strains of bacteria through our biological assay.