Date of Award
Summer 8-2011
Degree Type
Thesis-Restricted
Degree Name
M.S.
Degree Program
Chemistry
Department
Chemistry
Major Professor
Wang, Guijun
Second Advisor
Trudell, Mark L.
Third Advisor
Jursic, Branko S.
Abstract
Conformationally constrained bicyclic amino acids are invaluable in the synthesis of natural products and peptidomimetics. Aeruginosins contain novel bicyclic amino acid, 2--‐carboxy--‐6--‐hydroxyl octahydrindole (Choi) as the core structure. Aeruginosins are tetra peptide serine protease inhibitors isolated from marine sponges and cyanobacterial water blooms. Rigid bicyclic amino acid(Choi)is an essential core structure, which strongly influences biological activity of aeruginosin family members. Aeruginosins showed promising inhibitory activity against thrombin, trypsin, and factor VIIa. Thrombin and factor VIIa play a major role in blood clotting cascade; excessive coagulation leads to thrombosis and other cardiovascular diseases. Several research groups have reported a number of synthetic aeruginosin analogs.
In this thesis, some of the synthetic methodologies of bicyclic amino acid core of aeruginosins are presented. Importance of bicyclic amino acids in peptidomimetic synthesis and drug designing is presented. Mainly, syntheses of ring oxygenated Choi analogs starting from glucose and mannose are presented.
Recommended Citation
Dodlapati, Sanjeeva, "Synthesis of chiral intermediates by deritivization of monosaccharides" (2011). University of New Orleans Theses and Dissertations. 457.
https://scholarworks.uno.edu/td/457
Rights
The University of New Orleans and its agents retain the non-exclusive license to archive and make accessible this dissertation or thesis in whole or part in all forms of media, now or hereafter known. The author retains all other ownership rights to the copyright of the thesis or dissertation.