Chemistry Department
824A Hamilton Hall
University of Nebraska-Lincoln
Lincoln, Nebraska 68588 United States
dberkowitz1@unl.edu
Current research:
Our group uses the power of stereocontrolled organic synthesis to address questions in biological chemistry, particularly those related to protein-ligand interactions. For example, the first catalytic, asymmetric synthesis of (-)-podophyllotoxin serves as a tool us to examine how the structure of the E-ring affects drug binding to tubulin. Total synthesis has yielded compounds more potent than the natural product itself, both in the tubulin assay and against human cancer cell lines.
2016
“Zipped Synthesis” by Cross-Metathesis Provides a Cystathionine β‑Synthase Inhibitor that Attenuates Cellular H2S Levels and Reduces Neuronal Infarction in a Rat Ischemic Stroke Model, Christopher D. McCune, Su Jing Chan, Matthew L. Beio, Weijun Shen, Woo Jin Chung, Laura M. Szczesniak, Chou Chai, Shu Qing Koh, Peter T.-H. Wong, and David B. Berkowitz
2015
Exploiting Enzymatic Dynamic Reductive Kinetic Resolution (DYRKR) in Stereocontrolled Synthesis, Gregory A. Applegate and David B. Berkowitz
Mini-ISES identifies promising carbafructopyranose-based salens for asymmetric catalysis: Tuning ligand shape via the anomeric effect, Kannan R. Karukurichi, Xiang Fei, Robert A. Swyka, Sylvain Broussy, Weijun Shen, Sangeeta Dey, Sandip K. Roy, and David B. Berkowitz
2014
Phosphatase-Inert Glucosamine 6‑Phosphate Mimics Serve as Actuators of the glmS Riboswitch, Xiang Fei, Thomas Holmes, Julianna Diddle, Lauren Hintz, Dan Delaney, Alex Stock, Danielle Renner, Molly McDevitt, David B. Berkowitz, and Juliane K. Soukup
2012
Halocarbocyclization Entry into the Oxabicyclo[4.3.1]decyl Exomethylene-δ-Lactone Cores of Linearifolin and Zaluzanin A - Exploiting Combinatorial Catalysis, Sandeep K. Ginotra, Jacob A. Friest, and David B. Berkowitz
Unleashing a “True” pSer-Mimic in the Cell, Kaushik Panigrahi, David L. Nelson, and David B. Berkowitz
2011
Combinatorial Catalysis Assisted by a Visible Enzymatic Beacon in Real Time: New Synthetically Versatile (Pseudo)Halometalation/Carbocyclizations, Jacob A. Friest, Sylvain Broussy, Woo Jin Chung, and David B. Berkowitz
2010
Atomic details of near-transition state conformers for enzyme phosphoryl transfer revealed by MgF3− rather than by phosphoranes, Nicola J. Baxter, Matthew W. Bowler, Tooba Alizadeh, Matthew J. Cliff, Andrea M. Hounslow, Bin Wu, David B. Berkowitz, Nicholas H. Williams, G. Michael Blackburn, and Jonathan P. Waltho
Use of a Robust Dehydrogenase from an Archael Hyperthermophile in Asymmetric Catalysis–Dynamic Reductive Kinetic Resolution Entry into (S)-Profens, Jacob A. Friest, Yukari Maezato, Sylvain Broussy, Paul H. Blum, and David B. Berkowitz
2009
The α,α-Difluorinated Phosphonate L-pSer-Analogue: An Accessible Chemical Tool for Studying Kinase-Dependent Signal Transduction in Vitro, and In Living Cells, Kaushik Panigrahi, MariJean Eggen, Jun-Ho Maeng, Quanrong Shen, and David B. Berkowitz
2008
Use of Fluorinated Functionality in Enzyme Inhibitor Development: Mechanistic and Analytical Advantages, David B. Berkowitz, Kannan R. Karukurichi, Roberto de la Salud-Bea, David L. Nelson, and Christopher D. McCune
A Set of Phosphatase-Inert “Molecular Rulers” to Probe for Bivalent Mannose 6-Phosphate Ligand-Receptor Interactions, Xiang Fei, Christopher M. Connelly, Richard G. MacDonald, and David B. Berkowitz
2007
A Set of Phosphatase-Inert “Molecular Rulers” to Probe for Bivalent Mannose 6-Phosphate Ligand-Receptor Interactions, Xiang Fei, Christopher M. Connelly, Richard G. MacDonald, and David B. Berkowitz
Examination of the New α-(2′Z-Fluoro)vinyl Trigger with Lysine Decarboxylase: The Absolute Stereochemistry Dictates the Reaction Course, Kannan R. Karukurichi, Roberto de la Salud-Bea, Wan Jin Jahng, and David B. Berkowitz
Topoisomerase II-Drug Interaction Domains: Identification of Substituents on Etoposide that Interact with the Enzyme, Amy M. Wilstermann, Ryan P. Bender, Murrell Godfrey, Sungjo Choi, Clemens Anklin, David B. Berkowitz, Neil Osheroff, and David E. Graves
2006
α-Vinylic amino acids: occurrence, asymmetric synthesis, and biochemical mechanisms, David B. Berkowitz, Bradley D. Charette, Kannan Karukurichi, and Jill M. McFadden
A Formal [3,3]-Sigmatropic Rearrangement Route to Quaternary α-Vinyl Amino Acids: Use of Allylic N-PMP Trifluoroacetimidates, David B. Berkowitz, Bin Wu, and Huijie Li
Protein Structure Similarity Clustering: Dynamic Treatment of PDB Structures Facilitates Clustering, Bradley D. Charette, Richard G. MacDonald, Stefan Wetzel, David B. Berkowitz, and Herbert Waldmann
2005
In Situ Screening To Optimize Variables in Organic Reactions, David Berkowitz, Mohua Bose, and Sungjo Choi
2004
In situ enzymatic screening (ISES) of P,N-ligands for Ni(0)- mediated asymmetric intramolecular allylic amination, David B. Berkowitz, Weijun Shen, and Gourhari Maiti
1996
A Convenient Synthesis of L-α-Vinylglycine from L-Homoserine Lactone, David B. Berkowitz and Marianne K. Smith
1995
Free α-Oxiranyl Amino Acids, David B. Berkowitz and Michelle L. Pedersen
Enantiomerically Enriched α-Methyl Amino Acids. Use of an Acyclic, Chiral Alanine-Derived Dianion with a High Diastereofacial Bias., David B. Berkowitz and Marianne K. Smith