Dr. Kamal Bouhadir
Associate Professor
Organic Chemistry
B.Sc., American University of Beirut (1987) M.Sc., Auburn University (1991) Ph.D., Auburn University (1996).
Office: Chemistry 412
Phone: 3984
E-mail: kb05@aub.edu.lb
Research
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My research interests are focused on the synthesis of potential building blocks for the preparation of carbocyclic oligodeoxynucleotide (ODN) analogs. The demand for synthetic ODNs has increased rapidly during the last decade. Significant potentials of these polymers range from their uses in diagnostic (biosensors) to therapeutic applications (antisense, antigene). We are interested in the design and synthesis of a variety of non-conjugated dienes with nucleic bases attached. One series includes 1,6-heptadienes with nucleic bases attached either directly or via a linker to the central carbon. Another series includes a diallylamino group substituent attached to the nucleic bases. Our interest in these molecules stems from their potential utility to cyclopolymerize and form carbocyclic ODN analogs with a cyclopentane ring replacing the furanose ring and a hydrocarbon backbone replacing the phosphodiester backbone in natural ODNs. These analogs are expected to be physiologically more stable than their natural counterparts, and, therefore, less susceptible to enzymatic degradation in biological environments.
Selected Publications
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Two simple protocols for the preparation of diallylaminoethyl-substituted nucleic bases: a comparison, Tetrahedron Lett. 2006, 47, 1767-1770 (with R. S. Shatila).
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Synthesis of 4-[(1H,3H)-pyrimidine-2,4-dion-1-yl]- & 4-[(1H,3H)-5-methylpyrimidine-2,4-dion-1-yl]-1,6-heptadienes, Synth. Commun. 2005, 35(7), 1003-1010 (with J. L. Zhou and P. B. Shevlin).
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Controlled degradation of hydrogels using multi-functional cross-linking molecules, Biomaterials 2004, 25 (13), 2461-2466 (with K. Y. Lee and D. J. Mooney).
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Synthesis of purine- and pyrimidine-substituted heptadienes. The stereochemistry of cyclization and cyclopolymerization products, J. Org. Chem. 2003, 68 (4), 1235-1241 (with J. Y. Tsai, J. L. Zhou, T. R. Webb, Y. Sun and P. B. Shevlin).