Date of Award
Prof. Guijun Wang
Prof. Mark L Trudell
Prof. Branko S Jursic
Prof. John B Wiley
Aeruginosins are a family of marine natural products containing mostly non-proteogenic amino acids. These compounds contain a common 2-carboxy-6-hydroxy-octaindole (Choi) rigid bicyclic structure. Many aeruginosins are inhibitors for enzymes involved in the blood coagulation cascade, such as thrombin and Factor VIIa. In order to understand the structure activity relationship (SAR) of the aeruginosins and to discover novel anticoagulants with potentially improved inhibitory and pharmacokinetic properties, in the first part of my thesis I have discussed, synthesis of a series of novel analogs of aeruginosin 298-A, in which the Choi will be replaced with L-proline and oxygenated Choi analogs, and the Argol is replaced with various other functionalities. The preparation of oxygenated Choi analogs starting from glucose using a new method has been discussed.
In the second part of my dissertation, I have discussed the design, synthesis and self–assembly of glucosamine based hydro and organogelators. Carbohydrate-based low molecular weight gelators are an interesting class of molecules with many potential applications. A series of amides and ureas were prepared from the protected D-glucosamine from the corresponding acid chloride and isocyanates. The self-assembling properties of these compounds were studied in several solvents, including water and aqueous solutions. Most of these compounds were found to be efficient low molecular weight hydrogelators (LMHGs) for aqueous solutions. The preparation and characterization of these compounds will be elaborated.
goyal, Navneet, "Synthesis and biological evaluation of aeruginosin based compounds and self-assembly of glucosamine based compounds" (2011). University of New Orleans Theses and Dissertations. 1395.