David Berkowitz
Professor
Department of Chemistry
810 Hamilton Hall
phone: (402) 472-2738
email: dbb@unlserve.unl.edu
David Berkowitz 's Chemistry Web Page
Current Research
Dr. David Berkowitz is active at the interface of synthetic organic chemistry and enzymatic chemistry. Projects in the group include the synthesis and study of unnatural analogues of biological molecules that have been designed to display interesting properties. This includes (a) fluorinated phosphonates designed to act as stable phosphate surrogates or ‘teflon phosphates,’ (b) unnatural, alpha-branched amino acids designed to function as ‘Trojan horse inactivators’ for vitamin B-6 dependent enzymes, and (c) unnatural analogues of the lignan natural product (-)-podophyllotoxin, designed to probe its binding to tubulin. Synthetic methodology development becomes part and parcel of these endeavors.
The newest area of activity in the group is in catalyst development. In particular, we are attempting to address the need for efficient and information-rich screening methods to support combinatorial approaches to catalyst discovery and optimization. This has led to the development of a method that we term In Situ Enzymatic Screening (ISES) that exploits enzyme-based reporters enabling the experimentalist to rapidly rank catalysts, ideally, in terms of relative rate and stereoselectivity. The scope, limitations and application of this technology are currently under investigation.
Recent Key Publications
David B. Berkowitz, Mohua Bose and Sungjo Choi “In Situ Enzymatic Screening (ISES): A Tool for Catalyst Discovery and Reaction Development”, Angew. Chem. Int. Ed. Engl. 41, 1603-1607 (2002).
David B. Berkowitz and Mohua Bose “(Alpha-Monofluoroalkyl) phosphonates:
A Class of Isoacidic and ‘Tunable’ Mimics of Biological Phosphates”, J. Fluor. Chem. 112, 13-33 (2001).
David B. Berkowitz, Esmort Chisowa and Jill M. McFadden, “Stereocontrolled Synthesis of Quaternary Beta, Gamma-Unsaturated Amino Acids: Chain Extension of D- & L-Alpha-(2-Tributylstannyl)Vinyl Amino Acids”, Tetrahedron Symposia-in-Print 57, 6329-6343 (2001).
David B. Berkowitz, Jill M. McFadden, Esmort Chisowa and Craig L. Semerad “Organoselenium-Based Entry into Versatile, Alpha-(2-Tributylstannyl)vinyl Amino Acids in Scalemic Form: A New Route to Vinyl Stannanes”, J. Am. Chem. Soc. 122, 11031-11032 (2000).
Recent Graduate students and current affiliations
· Mohua Bose, (Ph.D. 2002-postdoctoral at Scripps Res. Inst.);
· Sungjo Choi, (Ph.D. 2001- postdoctoral at Texas A&M);
· Huijie Li, (M.S. 2001-GlaxoSmithKline);
· Esmort Chisowa, (M.S. 2001-Pfizer);
· Wan-Jin Jahng, (Ph.D. 2000-postdoctoral at Harvard);
· Jill McFadden, (Ph.D. 2000-NIH postdoctoral fellowship, Johns Hopkins)
