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Chemistry C329B

Ted Widlanski received his undergraduate degree from Columbia University. He subsequently received his doctorate from Harvard University in 1989 under the direction of Jeremy Knowles. Dr. Widlanski began his academic career at IU in the summer of 1989.

Dr. Widlanski’s research emphasizes an eclectic approach to solving biochemical and biomedical problems using a broad array of chemical approaches. This approach includes the design and evaluation of enzyme inhibitors, the elucidation of enzyme reaction mechanisms, the development of new synthetic methods to access important biologically active compound analogs and biological probes, and the study of components of signal transduction pathways, including those associated with a variety of disease states ranging from cancer to HIV.

Research

Our group concentrates on the development of methodologies to address problems of biochemical and biomedical interest. For example, the molecule shown below, an analogue of a naturally occurring oligonucleotide, holds promise for the treatment of viral diseases such as AIDS, for control of the unwanted expression of genetic information such as occurs in cancer cells, and for enhancing our understanding of the physical characteristics of nucleic acids and their interaction with proteins. We are also developing methodology for the synthesis and design of other kinds of unnatural nucleic acids, as well as saccharides, lipids, and a variety of enzyme inhibitors that are of potential therapeutic value.

The study of enzyme mechanisms by use of isotope effects, stereochemical probes, and artificial substrate analogues forms the basis for another area of research in our group. The development of functional group equivalents for the enhanced molecular recognition of protein ligands is an extension of our interest in the application of physical organic chemistry to the solution of biochemical problems. The use of such enhanced protein ligand interactions is being actively pursued for the development of antiviral agents and enzyme inhibitors.

We have also developed strategies for the potent and specific inhibitors of enzymes involved in signal transduction. Such advances should greatly facilitate the study of cell transformation and metabolism.

Publications

Asim K. Bera, Lena S. Polovnikova, Juliatek Roestamadji, Theodore S. Widlanski, George L. Kenyon, Michael J. McLeish and Miriam S. Hasson "Mechanism-based inactivation of benzoylformate decarboxylase, a thiamin diphosphate-dependent enzyme" J. Am.Chem.Soc. 129(14) 4120-4121 (2007)

Cheri L. Stowell, Kevin K. Barvian, Peter C.M.Young, Robert M. Bigsby, Dawn E. Verdugo, Carolyn R. Bertozzi and Theodore S. Widlanski "A Role for Sulfation- Desulfation in the Uptake of Bisphenol A into Breast Tumor Cells" Chemistry and Biology 13 , 891-897 (2006)

Levi S. Simpson and Theodore S. Widlanski "A Comprehensive Approach to the Synthesis of Sulfate Esters" J. Am.Chem.Soc. 128 (5), 1605-1610 (2006)

David C. Johnson II and Theodore S. Widlanski "Facile Deprotection of O-Cbz-Protected Nucleosides by Hydrogenolysis: An Alternative to O-Benzyl Ether-Protected Nucleosides" Org. Lett. 6 (25) 4643-4646 (2004)

David C. Johnson II and Theodore S. Widlanski "A Reversible Safety-Catch Method for the Hydrogenolysis of N-Benzyl Moieties" Tetrahedron Lett ., 45 , 8483-8487 (2004)

David C. Johnson II and Theodore S. Widlanski "The Synthesis of Nucleoside Phosphates and Polyphosphates" Curr. Protocols Nuc. Acid Res. Unit 13.1, 1-27 (2003)

David C. Johnson II and Theodore S. Widlanski "Cerium (III) Chloride-Mediated Reactions of Sulfonamide Dianions" J. Org. Chem. 68, 5300-5309 (2003)

Benjamin T. Burlingham, Lisa M. Pratt, Ernest R. Davidson, Vernon J. Shiner, Jon Fong and Theodore S. Widlanski " 34 S Isotope Effect on Sulfate Ester Hydrolysis; Mechanistic Implications" J. Am. Chem. Soc. 125, 13036-13037 (2003)

Benjamin T. Burlingham and Theodore S. Widlanski "An Intuitive Look at the Relationship of K 1 and IC 50 : A More General Use for the Dixon Plot" J. Chem. Ed 80 (2) 214-218 (2003)

David C. Johnson II and Theodore S. Widlanski "Multiple Routes for the Synthesis of N - Acylsulfonamide-bridged Nucleosides" Synthesis 6, 809-815 (2002)

Benjamin T. Burlingham and Theodore S. Widlanski "Synthesis and Biological Activity of N-Sulfonylphosphoramidates: Probing the Electrostatic Preferences of Alkaline Phosphatase" J. Org. Chem. 66 (23) 7561-7567 (2001) Cover Article

Awards

• Indiana University President’s Circle Award
• Gill Fellow, Indiana University
• Alfred P. Sloan Research Fellow
• Camille Dreyfus Teacher-Scholar Award
• American Cancer Society Junior Faculty Research Award
• Outstanding Young Faculty Award, Indiana University
• Du Pont Fellow, Harvard University
• Fieser Award, Harvard University
• Phi Lambda Upsilon, Columbia University

Highlights