David B. Berkowitz

Professor
824A Hamilton Hall
University of Nebraska-Lincoln

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, Fig. 1 illustrates the first catalytic, asymmetric synthesis of (-)-podophyllotoxin, which 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.

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2016

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“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

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Exploiting Enzymatic Dynamic Reductive Kinetic Resolution (DYRKR) in Stereocontrolled Synthesis, Gregory A. Applegate and David B. Berkowitz

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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

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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

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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

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Unleashing a “True” pSer-Mimic in the Cell, Kaushik Panigrahi, David L. Nelson, and David B. Berkowitz

2011

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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

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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

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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 Helmuth Blum, and David B. Berkowitz

2009

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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

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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

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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

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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

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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

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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

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α-Vinylic amino acids: occurrence, asymmetric synthesis, and biochemical mechanisms, David B. Berkowitz, Bradley D. Charette, Kannan Karukurichi, and Jill M. McFadden

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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

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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

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In Situ Screening To Optimize Variables in Organic Reactions, David Berkowitz, Mohua Bose, and Sungjo Choi

2004

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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