Publications and Patents

Kaushik Panigrahi, David L. Nelson and David B. Berkowitz. “Unleashing a ‘True’ pSer-Mimic in the Cell.” Chemistry and Biology, 2012, 19, 666-667. .pdf

Sandeep K. Ginotra, Jacob A. Friest and David B. Berkowitz. “
Halocarbocyclization Entry into the Oxabicyclo[4.3.1]decyl Exomethylene--Lactone Cores of Linearifolin and Zaluzanin A: Exploiting Combinatorial Catalysis.” Organic Letters, 2012, 4, 968-971 .pdf

Jacob A. Friest, Sylvain Broussy, Woo Jin Chung, and David B. Berkowitz. “Combinatorial Catalysis Employing a Visible Enzymatic Beacon in Real Time: Synthetically Versatile (Pseudo)Halometalation/Carbocyclizations.” Angewandte Chemie, Int. Ed. 2011, 50, 8895-8899. pdf

Gregory A. Applegate, Ross W. Cheloha, David L. Nelson, and David B. Berkowitz. "A New Dehydrogenase from Clostridium acetobutylicum for Asymmetric Synthesis: Dynamic Reductive Kinetic Resolution entry into the Taxotère side chain." Chem Comm 2011, 47, 2420-2422. pdf
         Featured in:
SYNFACTS 2011, 3, 333. pdf

David B. Berkowitz, Sangeeta Dey, Kannan R. Karukurichi and Weijun Shen.  "A Method for Measuring the Stereoselectivity and Relative Rate for Organic Chemical Reactions."  U.S. Patent No. 7,767,388, issued August 3,

Jacob A. Friest, Yukari Maezato, Sylvain Broussy, Paul Blum, and David B. Berkowitz. "Use of a Robust Dehydrogenase from an Archael Hyperthermophile in Asymmetric Catalysis - Dynamic Reductive Kinetic Resolution Entry into (
S)-Profens." JACS 2010, 132, 5930-5931. pdf

         Featured in Chemical and Engineering News, 2010, 88 (16), 34- 35. link
         Featured in
SYNFACTS, 2010, 8, 861. .pdf

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. "Atomic details of near-transition state conformers for enzyme phosphoryl transfer revealed by MgF3 rather than by phosphoranes." PNAS 2010, 107 (10) 4555-4560. pdf

          Featured in
Chemical and Engineering News, 2010, 88 (9), 35. link

David B. Berkowitz ; Sylvain Broussy; Argiris Efstratiadis;  Apostolos Klinakis; Matthias Szabolcs.  (Columbia University In the City of   New York, USA; University of Nebraska).    “Analogues of (-)-Picropodophyllin,  Synthesis and Uses Thereof.” PCT Int. Appl.  2009, 114pp. CODEN: PIXXD2 WO 2009100349  A1  20090813

Kaushik Panigrahi, MariJean Eggen, Jun-Ho Maeng, Quanrong Shen, David B. Berkowitz* “The a,a-Difluorinated Phosphonate L-pSer-Analogue: An Accessible Chemical Tool for Studying Kinase-Dependent Signal Transduction, in Vitro and In Living Cells.” Chemistry and Biology  2009, 16(9), 928-936 pdf

David B. Berkowitz,* Kannan R. Karukurichi, Roberto de la Salud-Bea, Gourhari Maiti, Jill M. McFadden and Michelle L. Morris “Stereoselective Synthesis of Quaternary, alpha-Vinyl Amino Acids  and their alpha-(2’Z-Fluoro)vinyl Congeners – Promising Candidates for PLP Enzyme Inactivation.” ACS Symposium-In-Print 2009, 1009, 288-303. pdf

Broussy, Sylvain, Cheloha, Ross W., and Berkowitz, David B.. "Enantioselective, Ketoreductase-Based Entry into Pharmaceutical Building Blocks: Ethanol as Tunable Nicotinamide Reductant." Organic Letters 2009, 11(2), 305-308. pdf

David B. Berkowitz*, Kannan R. Karukurichi, Roberto de la Salud-Bea, David L. Nelson, and Christopher D. McCune, “Use of fluorinated functionality in enzyme inhibitor development: Mechanistic and analytical advantages,
J. Fluorine Chem.
2008, 129, 731–742.pdf

Fei, Xiang; Connelly, Christopher M.; MacDonald, Richard G.; Berkowitz, David B.. "A set of phosphatase-inert "molecular rulers" to probe for bivalent mannose 6-phosphate ligand-receptor interactions." Bioorganic & Medicinal Chemistry Letters 2008, 18(10), 3085-3089. pdf

Sangeeta Dey, Douglas R. Powell, Chunhua Hu, and David B. Berkowitz,* "Cassette"-ISES (In Situ Enzymatic Screening) Identifies Complementary Chiral Scaffolds for Hydrolytic Kinetic Resolution Across a Range of Epoxides. Angew. Chem. Int. Ed. 2007, 46, 7010-7014. pdf

Wilstermann, A. M.; Bender, R. P.; Godfrey, M.; Choi, S.; Anklin, C.; Berkowitz, D. B.; Osheroff, N.; Graves, D. E. “Topoisomerase II-Drug Interaction Domains: Identification of Substituents on Etoposide that Interact with the Enzyme.” Biochemistry 2007, 46, 8217-8225. pdf

Kannan R. Karukurichi, Roberto de la Salud-Bea, Wan Jin Jahng, David B. Berkowitz* “Examination of the New a-(2’Z-Fluoro)vinyl Trigger with Lysine Decarboxylase: The Absolute Stereochemistry Determines the Reaction Course ,” J. Am. Chem. Soc. 2007, 129, 258-259. pdf

Bradley D. Charette, Richard G. MacDonald, Stefan Wetzel, David B. Berkowitz* and Herbert Waldmann* (co-corresponding authors) “PSSC (Protein Structure Similarity Clustering): Dynamic Treatment of PDB Structures Facilitates Clustering, Angew. Chem. Int. Ed.2006, 45, 7766-7770. pdf

David B. Berkowitz,* Bradley D. Charette, Kannan R. Karukurichi and Jill M. McFadden “ a-Vinylic Amino Acids: Natural Occurrence, Asymmetric Synthesis and Biochemical Mechanisms .” Tetrahedron: Asymmetry 2006, 17, 869-882. pdf

David B. Berkowitz, Sangeeta Dey, Kannan R. Karukurichi and Weijun Shen “A Method for Measuring the Stereoselectivity and Relative Rate for Organic Chemical Reactions.” U.S. Patent Application, Serial No. 11/434,247, filed May 16, 2006.

David B. Berkowitz,* Bin Wu and Huijie Li “A Formal [3,3]-Sigmatropic Rearrangement Route to Quaternary a-Vinyl Amino Acids: Use of Allylic N-PMP Trifluoroacetimidates.” Org. Lett. 2006, 8, 971-974. pdf

Sangeeta Dey, Kannan R. Karukurichi,Weijun Shen, and David B. Berkowitz,* Double-Cuvette ISES: In Situ Estimation of Enantioselectivity and Relative Rate for Catalyst Screening.J. Am. Chem. Soc.2005, 127, 8610-8611.pdf

Weijun Shen, Molly K. McGath, Ruby Evande and David B. Berkowitz,* A Continuous Spectrophotometric Assay for Human Cystathionine Beta-Synthase.Analytical Biochemistry 2005, 342,1 103-110.pdf

David B. Berkowitz,* Gourhari Maiti, Bradley D. Charette, Christine D. Dreis and Richard G. MacDonald* Mono- and Bivalent Ligands Bearing Mannose 6-Phosphate (M6P) Surrogates: Targeting the M6P/Insulin-like Growth Factor II Receptor.
Org. Lett. 2004, 6, 4921-4924.pdf

David B. Berkowitz* and Gourhari Maiti Following an ISES Lead: The First Examples of Asymmetric Ni(0)-Mediated Allylic Amination.
Org. Lett. 2004, 6, 2661-2664.pdf

David B. Berkowitz, *Weijun Shen and Gourhari Maiti In Situ Enzymatic Screening (ISES) of P,N-Ligands for Ni(0)-Mediated Asymmetric, Intramolecular Allylic Amination. Tetrahedron: Asymmetry200415, 2845-2851. pdf

David B. Berkowitz, *Roberto de la Salud-Bea and Wan-Jin Jahng, Synthesis of Quaternary Amino Acids Bearing a (2'Z)-Fluorovinyl alpha-Branch: Potential PLP Enzyme Inactivators. Org. Lett. 2004, 6, 1821-1824.pdf

M.J. Huang,* S. Regunathan, M. Botta, K. Lee, E. McClendon, G. B. Yi, M. L. Pedersen, D. B. Berkowitz, G. Wang, M. Travagli and J. E. Piletz Structure-Activity Analysis of Guanidine Group in Agmatine for Brain Agmatinase,
Annals of the New York Academy of Sciences 2003 , 1009, 52-64.

David B. Berkowitz, * Mohua Bose and Sungjo Choi “Biphasic Process For In Situ Enzymatic Screening To Optimize Variables In Organic Reactions.” U.S. Pat. Appl. Publ. (2003), 47 pp. CODEN: USXXCO US 2003148257 A1 20030807 CAN 139:164340 AN 2003:609937

David B. Berkowitz, * Mohua Bose and Sungjo Choi In Situ Enzymatic Screening (ISES): A Tool for Catalyst Discovery and Reaction Development.
Angewandte Chemie International Edition, English 2002 , 41, 1603-1607. pdf

        Featured in
Chemical and Engineering News, 2002, 80 (21), 50.  link

David B. Berkowitz * and Mohua Bose “(alpha-monofluoroalkyl)phosphonates: A Class of Isoacidic and ‘Tunable’ Mimics of Biological Phosphates,”
Journal of Fluorine Chemistry 2001 , 112, 13-33 (invited).pdf

David B. Berkowitz, * Esmort Chisowa and Jill M. McFadden, Stereocontrolled Synthesis of Quaternary beta, gama -Unsaturated Amino Acids: Chain Extension of D- & L- alpha -(2-Tributylstannyl)Vinyl Amino Acids,
Tetrahedron Symposia-in-Print 2001 , 57, 6329-6343. pdf

David B. Berkowitz, * Mohua Bose and Nathan G. Asher, A Convergent Triflate Displacement Approach to ( alpha -Monofluoroalkyl)phosphonates,
Org. Lett. 2001 , 3, 2009-2012. pdf

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. 2000, 122, 11031-11032.pdf

David B. Berkowitz, * Mohua Bose, Travis J. Pfannenstiel and Tzanko Doukov alpha-Fluorinated Phosphonates as Substrate Mimics for Glucose 6-Phosphate Dehydrogenase: The CHF Stereochemistry Matters, J. Org. Chem. 2000, 65, 4498-4508. pdf

David B. Berkowitz Ring E-Modified Analogues of (-)-Podophyllotoxin and a Method for Their Synthesis, U.S. Patent No. 6,051,721 April 18, 2000.

David B. Berkowitz, * Sungjo Choi, Debnath Bhuniya and Richard K. Shoemaker Novel 'Reverse Kahne-Type Glycosylation': Synthesis of O-, N- and C-Linked Epipodophyllotoxin Conjugates. Org. Lett. 2000, 2, 1149-1152.pdf

David B. Berkowitz, * Jill M. McFadden and Marianne K. Sloss Engineering Acyclic Stereocontrol in the Alkylation of Vinylglycine-Derived Dianions: Asymmetric Synthesis of Higher a -Vinyl Amino Acids,
J. Org. Chem. 2000, 65, 2907-2918. pdf

David B. Berkowitz, * Sungjo Choi and Jun-Ho Maeng Enzyme-Assisted Asymmetric Total Synthesis of (-)-Podophyllotoxin and (-)-Picropodophyllin. J. Org. Chem. 2000, 65, 847-860.pdf

David B. Berkowitz and Michelle L. Pedersen alpha -Oxiranyl Amino Acids, U.S. Patent No. 6,008,386 December 28, 1999.

David B. Berkowitz, * Ryan Hartung and Sungjo Choi Enzymatic Hydrolysis of Advanced Synthetic Intermediates: On the Choice of the Organic Cosolvent. Tetrahedron: Asymmetry, 1999, 10, 4513-4520. pdf

David B. Berkowitz, * Debnath Bhuniya and Gorka Peris Facile Installation of the Phosphonate and ( alpha, alpha-Difluoromethyl)phosphonate Functionalities Equipped with Benzyl Protection.
Tetrahedron Letters, 1999, 40, 1869-1872.pdf

David B. Berkowitz, * Jill McFadden, Marianne K. Smith and Michelle L. Pedersen Synthesis of alpha-Vinyl Amino Acids. Methods in Molecular Medicine, PeptidomimeticsProtocols (Wieslaw M. Kazmierski, volume Ed.; John M. Walker, series Ed.; Humana Press, Totowa, NJ), Vol. 23, Chapter 27, 467-488, 1999.pdf

David B. Berkowitz & Michelle L. Pedersen A Method for the Synthesis of alpha-Oxiranyl Amino Acids, U.S. Patent No. 5,705,660; January 6, 1998

David B. Berkowitz, * Wan-Jin Jahng and Michelle L. Pedersen (±)- a-Vinyllysine and (±)- alpha-Vinylarginine are Time-Dependent Inhibitors of Their Cognate Decarboxylases. Bioorganic and Medicinal Chemistry Letters 1996, 6, 2151-2156.pdf

David B. Berkowitz, * Jun-Ho Maeng, A.H. Dantzig, R.L. Shepard & B.H. Norman Chemoenzymatic and Ring E-Modular Approach to the (-)-Podophyllotoxin Skeleton. Synthesis of 3',4',5'-Tridemethoxy-(-)-podophyllotoxin,
J. Am. Chem. Soc. (Communication) 1996, 118, 9426-9427.pdf

David B. Berkowitz, * MariJean Eggen, Quanrong Shen and Richard K. Shoemaker Ready Access to Fluorinated Phosphonate Mimics of Secondary Phosphates. Synthesis of the ( alpha, alpha-Difluoroalkyl)phosphonate Analogues of L-Phosphoserine, L-Phosphoallothreonine and L-Phosphothreonine, 
J. Org. Chem. 1996, 61, 4666-4675.pdf

David B. Berkowitz, * Michelle L. Pedersen and Wan-Jin Jahng Synthesis of Higher alpha-Chlorovinyl and alpha-Bromovinyl Amino Acids: The Amino Protecting Group Determines the Reaction Course,
Tetrahedron Letters1996, 37, 4309-4312.pdf

David B. Berkowitz * and Jun-Ho Maeng Enantioselective Entry into Benzoxabicyclo[2.2.1]heptyl Systems by Enzymatic Desymmetrization: Toward Chiral Building Blocks for Lignan Synthesis,
Tetrahedron: Asymmetry1996, 7, 1577-1580.

David B. Berkowitz * and Marianne K. Smith, A Convenient Synthesis of L-Vinylglycine from L-Homoserine Lactone. Synthesis , 1996, 39-41. pdf

David B. Berkowitz * and Darby G. Sloss  Diallyl Lithiodifluoromethylphosphonate: A New Reagent for the Introduction of the (Difluoromethylene)phosphonate Functionality. J. Org. Chem. 1995 , 60 , 7047-7050.pdf

David B. Berkowitz * and Michelle L. Pedersen Free alpha -Oxiranyl Amino Acids.
J. Org. Chem. 1995 , 60 , 5368-5369. pdf

David B. Berkowitz * and Marianne K. Smith Enantiomerically Enriched alpha -Methyl Amino Acids. Alkylation of an Acyclic, Chiral Alanine Dianion with a High Diastereofacial Bias. J. Org. Chem. 1995, 60 , 1233-1238.pdf

David B. Berkowitz, * James A. Pumphrey and Quanrong Shen Enantiomerically Enriched a-Vinyl Amino Acids via Lipase-Mediated Reverse Transesterification, Tetrahedron Letters 1994, 35, 8743-8746.pdf

David B. Berkowitz, * Quanrong Shen and Jun-Ho Maeng Synthesis of the (alpha, alpha-Difluoroalkyl)phosphonate Analogue of Phosphoserine.  Tetrahedron Letters 1994, 35, 6445-6448.pdf

David B. Berkowitz * and Michelle L. Pedersen Simultaneous Amino and Carboxyl Group Protection for alpha-Branched Amino Acids.
J. Org. Chem.1994, 59, 5476-5478.pdf

Quanrong Shen, Darby G. Sloss, David B. Berkowitz * Displacement of Primary Sugar Triflates with C-Nucleophiles: D-Glucopyranose and D-Ribofuranose Functionalization and Chain Extension, Synthetic Communications 1994, 24 , 1519-1530.

Michelle L. Pedersen and David B. Berkowitz * Formal alpha-Vinylation of Amino Acids. Use of a New Benzeneselenolate Equivalent.J. Org. Chem. 1993, 58, 6966-6975. pdf

David B. Berkowitz * , MariJean Eggen, Quanrong Shen and Darby G. Sloss Synthesis of (alpha , alpha -Difluoroalkyl)phosphonates by Displacement of Primary Triflates. J. Org. Chem. 1993, 58 , 6174-6176. pdf

Michelle L. Pedersen and David B. Berkowitz* A Reagent for the Efficient Cleavage of N-Benzoylhomoserine Lactones: Access to alpha-(2-phenylseleno)ethyl Amino Acids. Tetrahedron Letters 1992, 33, 7315-7318. pdf