Babak Borhan
Associate Professor Office: 527 Chemistry
Phone: 517-355-9715 138 /
Websites: Research Group - Area
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Synthetic and Bioorganic Chemistry
(Research Description PDF - 1390 kb)The research interests of our lab can be subdivided into the three main areas of Bioorganic Chemistry, Synthetic Chemistry, and Organic Spectroscopy.
Our Bioorganic Chemistry efforts are geared towards elucidation of enzymatic mechanisms and the interaction of bioactive compounds with receptors and proteins. We rely heavily on de novo protein design and mimicry of natural systems to better understand how certain biological processes occur. As an example, we have initiated research into designing protein mimics of rhodopsin, the protein responsible for vision, which can bind retinal as a protonated Schiff base [PSB] (same binding mode as in rhodopsin). These protein mimics will be used to investigate the wavelength regulation mechanism that enables color vision. Other proteins under investigation include Retinoic Acid Receptor (RAR) and related systems, which are of paramount importance in embryonic development, and also play a central role in oncogenesis. We are also engaged in the study of a new class of fatty acid metabolites, THF-Diols of Arachidonic Acid, which can trigger the release of Ca2+ within cells.
Our Synthetic Chemistry program is generally focused on the development of new reactions that utilize simple organic molecules and through designed manipulations lead to more complex systems. In most cases, our methodologies lead to the production of heterocycles with regio- and stereocontrol. These transformations are then highlighted in total syntheses of natural products that exhibit interesting biological activities. As an example, the ylide-based Payne or aza-Payne rearrangement of hydroxyepoxides or hydroxyaziridines lead to the formation of THF or pyrrolidine rings with complete stereochemical fidelity. These reactions are used to synthesize molecules such as mucoxin and hateramulide NA.
In the area of Organic Spectroscopy, we are interested in developing host/guest systems that can be used in the absolute stereochemical determination of chiral compounds. We accomplish this through the design and synthesis of chromophoric receptors, which upon binding with the chiral compound function as reporters of chirality. We rely heavily on Circular Dichroism (CD) as the tool for observing the host/guest interactions between the chiral compounds and the receptors. In particular, we will take advantage of the excitonic coupling between independently conjugated chromophores that make up the receptors to establish non-empirical guidelines for the absolute stereochemical determination of asymmetric centers
Selected Publications
One-Pot Regio- and Stereoselective Cyclization of 1,2,n-Triols, Zheng, T., Narayan, R. S., Schomaker, J. M., Borhan, B., J. Am. Chem. Soc. 2005, 127, 6946-6947.Synthesis of Diastereomerically and Enantiomerically Pure 2,3-disubstituted Tetrahydrofurans Using a Sulfoxonium Ylide, Schomaker, J. M., Pulgam, V. R., Borhan, B., J. Am. Chem. Soc. 2004, 126, 13600-13601.
Direct Lactonization of Alkenols via Osmium Tetroxide-Mediated Oxidative Cleavage, Schomaker, J. M.; Travis, B. R.; Borhan, B., Org. Lett. 2003, 5, 3089-3092.
Facile Oxidation of Aldehydes to Acids and Esters with Oxone, Travis, B. R.; Sivakumar, M.; Hollist, G. O.; Borhan, B., Org. Lett. 2003, 5, 1031-1034.
Absolute Stereochemical Determination of Chiral Carboxylic Acids, Yang, Q., Olmsted, C., Borhan, B., Org. Lett. 2002, 4, 3423-3426.
Osmium Tetroxide Promoted Catalytic Oxidative Cleavage of Olefins. An Organometallic Ozonolysis, B. Travis, R. S. Narayan, and B. Borhan, J. Am. Chem. Soc. 2002, 124, 3824-3825.
Movement of Retinal Along the Visual Transduction Path, B. Borhan, M. L. Souto, H. Imai, Y. Shichida, and K. Nakanishi, Science 2000, 288, 2209-2212.
