Address

Fulmer 477
Pullman, WA 99164-4630

(509) 335-7613
email: cberkman@wsu.edu

Education

• BA Chemistry (Honors), 1986
  Lake Forest College, Lake Forest, IL
• PhD Chemistry, 1993
  Loyola University of Chicago, Chicago, IL

Research

Synthesis, resolution, and biochemical evaluation of chiral phosphorus-containing inhibitors of metallopeptidases related to cancer, folate processing, and neurodegenerative diseases.

The research in my laboratory is primarily concerned with design of novel enzymes inhibitors for the use in sensitizing tumor cells to common chemotherapeutic strategies. Specifically, we are interested in phosphorus- and sulfur-containing transition-state analogs inhibitors of these target enzymes. To this end, we focus also on the preparation of conformationally restricted substrates for such enzymes in order to probe their structural requirements and to ultimately design analogous inhibitors with enhanced selectivity.

We are also interested in the design and synthesis of conformationally constrained molecules for use as pro-prodrugs. Such molecules require a primary bioactivation step which is followed by a rapid intramolecular release of a drug. Consequently, these compounds may allow for the specific or timed release of potent drugs at a desired site of action.

Finally, we are beginning to design and develop novel synthetic alternatives to the organophosphorus insecticide Malathion. Such compounds will be designed to be insensitive to the secondary problems associated with acute poisoning by impurities found in commercial Malathion formulations. Utilizing our current understanding of the mechanism by which these impurities act to inhibit target enzymes, we will construct synthetic analogs that both confirm this mechanism and circumvent it.

Publications

• Substrate Specificity of Prostate-Specific Membrane Antigen. Santiago, N.; Moser, J.*; Rowley, J.A.*; Davis, E. Anderson, M.O.; Berkman, C.E. Bioorg. Med. Chem. 2006 (Submitted)
• Purification of Prostate-Specific Membrane Antigen with Conformational Epitope-Specific Antibody-Affinity Chromatography. Liu, T.; Toriyabe, Y.; Berkman, C.E. Prot. Exp. Purif. 2006, 49, 251.
• Optimizing Phenethylphosphonamidates for the Inhibition of Prostate-Specific Membrane Antigen. Wone, D.W.G.; Rowley, J.A.*; Garofalo, A.W.; Berkman, C.E. Bioorg. Med. Chem. 2006, 14, 67.
  Synthesis of N-Phosphoryl Amino Acids Using Bis(9-fluorenylmethyl) Phosphite. Wu, L.* C.E. Berkman, C.E. Tetrahedron Lett. 2005, 46, 5301.
• Stereoselective Inhibition of Glutamate Carboxypeptidase by Organophosphorus Derivatives of Glutamic Acid. Mallari, J. P.*; Choy, C.J.*; Hu, Y.; Martinez, A.R.*; Hosaka, M.*; Toriyabe, Y.*; Maung, J.*; Blecha, J.E.*; Pavkovic, S. F.; Berkman, C. E.Bioorg. Med. Chem., 2004, 12, 6011