David B Berkowitz, PhD

  • 2429 Citations
  • 32 h-Index
1987 …2020

Research output per year

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Article
2020

A Hammett Study of Clostridium acetobutylicum Alcohol Dehydrogenase (CaADH): An Enzyme with Remarkable Substrate Promiscuity and Utility for Organic Synthesis

Kudalkar, G. P., Tiwari, V. K., Lee, J. D. & Berkowitz, D. B., 2020, In : Synlett. 31, 3, p. 237-247 11 p., st-2010-r0669-c.

Research output: Contribution to journalArticle

2 Scopus citations
2019

Mix-and-inject XFEL crystallography reveals gated conformational dynamics during enzyme catalysis

Dasgupta, M., Budday, D., de Oliveira, S. H. P., Madzelan, P., Marchany-Rivera, D., Seravalli, J., Hayes, B., Sierra, R. G., Boutet, S., Hunter, M. S., Alonso-Mori, R., Batyuk, A., Wierman, J., Lyubimov, A., Brewster, A. S., Sauter, N. K., Applegate, G. A., Tiwari, V. K., Berkowitz, D. B., Thompson, M. C. & 5 others, Cohen, A. E., Fraser, J. S., Wall, M. E., van den Bedem, H. & Wilson, M. A., Dec 17 2019, In : Proceedings of the National Academy of Sciences of the United States of America. 116, 51, p. 25634-25640 7 p.

Research output: Contribution to journalArticle

3 Scopus citations

Rapid Entry into Biologically Relevant α,α-Difluoroalkylphosphonates Bearing Allyl Protection-Deblocking under Ru(II)/(IV)-Catalysis

Panigrahi, K., Fei, X., Kitamura, M. & Berkowitz, D. B., Dec 20 2019, In : Organic Letters. 21, 24, p. 9846-9851 6 p.

Research output: Contribution to journalArticle

2 Scopus citations
2018

Crystal Structures of Cystathionine β-Synthase from Saccharomyces cerevisiae: One Enzymatic Step at a Time

Tu, Y., Kreinbring, C. A., Hill, M., Liu, C., Petsko, G. A., McCune, C. D., Berkowitz, D. B., Liu, D. & Ringe, D., Jun 5 2018, In : Biochemistry. 57, 22, p. 3134-3145 12 p.

Research output: Contribution to journalArticle

5 Scopus citations
2017

A thiocyanopalladation/carbocyclization transformation identified through enzymatic screening: Stereocontrolled tandem C-SCN and C-C bond formation

Malik, G., Swyka, R. A., Tiwari, V. K., Fei, X., Applegate, G. A. & Berkowitz, D. B., 2017, In : Chemical Science. 8, 12, p. 8050-8060 11 p.

Research output: Contribution to journalArticle

11 Scopus citations

General Linker Diversification Approach to Bivalent Ligand Assembly: Generation of an Array of Ligands for the Cation-Independent Mannose 6-Phosphate Receptor

Fei, X., Zavorka, M. E., Malik, G., Connelly, C. M., MacDonald, R. G. & Berkowitz, D. B., Aug 18 2017, In : Organic Letters. 19, 16, p. 4267-4270 4 p.

Research output: Contribution to journalArticle

4 Scopus citations

Human serine racemase structure/activity relationship studies provide mechanistic insight and point to position 84 as a hot spot for β-elimination function

Nelson, D. L., Applegate, G. A., Beio, M. L., Graham, D. L. & Berkowitz, D. B., Aug 25 2017, In : Journal of Biological Chemistry. 292, 34, p. 13986-14002 17 p.

Research output: Contribution to journalArticle

6 Scopus citations

Synthesis and Deployment of an Elusive Fluorovinyl Cation Equivalent: Access to Quaternary α-(1′-Fluoro)vinyl Amino Acids as Potential PLP Enzyme Inactivators

McCune, C. D., Beio, M. L., Sturdivant, J. M., De La Salud-Bea, R., Darnell, B. M. & Berkowitz, D. B., Oct 11 2017, In : Journal of the American Chemical Society. 139, 40, p. 14077-14089 13 p.

Research output: Contribution to journalArticle

20 Scopus citations

The In Situ Enzymatic Screening (ISES) Approach to Reaction Discovery and Catalyst Identification

Swyka, R. A. & Berkowitz, D. B., Dec 14 2017, In : Current protocols in chemical biology. 9, 4, p. 285-305 21 p.

Research output: Contribution to journalArticle

1 Scopus citations
2016

Zipped synthesis by cross-metathesis provides a cystathionine ß-synthase inhibitor that attenuates cellular H2S levels and reduces neuronal infarction in a rat ischemic stroke model

McCune, C. D., Chan, S. J., Beio, M. L., Shen, W., Chung, W. J., Szczesniak, L. M., Chai, C., Koh, S. Q., Wong, P. T. H. & Berkowitz, D. B., Apr 27 2016, In : ACS Central Science. 2, 4, p. 242-252 11 p.

Research output: Contribution to journalArticle

27 Scopus citations
2015

A useful methoxyvinyl cation equivalent: α-t-butyldimethylsilyl-α-methoxyacetaldehyde

Mccune, C. D., Beio, M. L., Friest, J. A., Ginotra, S. & Berkowitz, D. B., May 25 2015, In : Tetrahedron Letters. 56, 23, p. 3575-3579 5 p., 45992.

Research output: Contribution to journalArticle

2 Scopus citations
17 Scopus citations

Mini-ISES identifies promising carbafructopyranose-based salens for asymmetric catalysis: Tuning ligand shape via the anomeric effect

Karukurichi, K. R., Fei, X., Swyka, R. A., Broussy, S., Shen, W., Dey, S., Roy, S. K. & Berkowitz, D. B., Jul 2015, In : Science Advances. 1, 6, e1500066.

Research output: Contribution to journalArticle

6 Scopus citations
2014

Phosphatase-inert glucosamine 6-phosphate mimics serve as actuators of the glms riboswitch

Fei, X., Holmes, T., Diddle, J., Hintz, L., Delaney, D., Stock, A., Renner, D., McDevitt, M., Berkowitz, D. B. & Soukup, J. K., Dec 19 2014, In : ACS chemical biology. 9, 12, p. 2875-2882 8 p.

Research output: Contribution to journalArticle

16 Scopus citations
2012

Halocarbocyclization entry into the oxabicyclo[4.3.1]decyl exomethylene-δ-lactone cores of linearifolin and zaluzanin A: Exploiting combinatorial catalysis

Ginotra, S. K., Friest, J. A. & Berkowitz, D. B., Feb 17 2012, In : Organic Letters. 14, 4, p. 968-971 4 p.

Research output: Contribution to journalArticle

15 Scopus citations
2011

A new dehydrogenase from Clostridium acetobutylicum for asymmetric synthesis: Dynamic reductive kinetic resolution entry into the Taxotère side chain

Applegate, G. A., Cheloha, R. W., Nelson, D. L. & Berkowitz, D. B., Feb 7 2011, In : Chemical Communications. 47, 8, p. 2420-2422 3 p.

Research output: Contribution to journalArticle

35 Scopus citations

Combinatorial catalysis employing a visible enzymatic beacon in real time: Synthetically versatile (Pseudo)halometalation/carbocyclizations

Friest, J. A., Broussy, S., Chung, W. J. & Berkowitz, D. B., Sep 12 2011, In : Angewandte Chemie - International Edition. 50, 38, p. 8895-8899 5 p.

Research output: Contribution to journalArticle

17 Scopus citations
2010

Atomic details of near-transition state conformers for enzyme phosphoryl transfer revealed by MgF3- rather than by phosphoranes

Baxter, N. J., Bowler, M. W., Alizadeh, T., Cliff, M. J., Hounslow, A. M., Wu, B., Berkowitz, D. B., Williams, N. H., Blackburn, G. M. & Waltho, J. P., Mar 9 2010, In : Proceedings of the National Academy of Sciences of the United States of America. 107, 10, p. 4555-4560 6 p.

Research output: Contribution to journalArticle

64 Scopus citations

Use of a robust dehydrogenase from an archael hyperthermophile in asymmetric catalysis-dynamic reductive kinetic resolution entry into (s)-profens

Friest, J. A., Maezato, Y., Broussy, S., Blum, P. & Berkowitz, D. B., May 5 2010, In : Journal of the American Chemical Society. 132, 17, p. 5930-5931 2 p.

Research output: Contribution to journalArticle

62 Scopus citations
2009

Enantioselective, ketoreductase-based entry into pharmaceutical building blocks: Ethanol as tunable nicotinamide reductant

Broussy, S., Cheloha, R. W. & Berkowitz, D. B., Jan 15 2009, In : Organic Letters. 11, 2, p. 305-308 4 p.

Research output: Contribution to journalArticle

55 Scopus citations
2008
16 Scopus citations
2007
32 Scopus citations

Examination of the new α-(2′Z-fluoro)vinyl trigger with lysine decarboxylase: The absolute stereochemistry dictates the reaction course

Karukurichi, K. R., De La Salud-Bea, R., Jahng, W. J. & Berkowitz, D. B., Jan 17 2007, In : Journal of the American Chemical Society. 129, 2, p. 258-259 2 p.

Research output: Contribution to journalArticle

22 Scopus citations

Topoisomerase II-drug interaction domains: Identification of substituents on etoposide that interact with the enzyme

Wilstermann, A. M., Bender, R. P., Godfrey, M., Choi, S., Anklin, C., Berkowitz, D. B., Osheroff, N. & Graves, D. E., Jul 17 2007, In : Biochemistry. 46, 28, p. 8217-8225 9 p.

Research output: Contribution to journalArticle

54 Scopus citations
2006

A formal [3,3]-sigmatropic rearrangement route to quaternary α-vinyl amino acids: Use of allylic N-PMP trifluoroacetimidates

Berkowitz, D. B., Wu, B. & Li, H., Mar 2 2006, In : Organic Letters. 8, 5, p. 971-974 4 p.

Research output: Contribution to journalArticle

22 Scopus citations

Protein structure similarity clustering: Dynamic treatment of PDB structures facilitates clustering

Charette, B. D., MacDonald, R. G., Wetzel, S., Berkowitz, D. B. & Waldmann, H., Nov 27 2006, In : Angewandte Chemie - International Edition. 45, 46, p. 7766-7770 5 p.

Research output: Contribution to journalArticle

15 Scopus citations
2005

A continuous spectrophotometric assay for human cystathionine beta-synthase

Shen, W., McGath, M. K., Evande, R. & Berkowitz, D. B., Jul 1 2005, In : Analytical Biochemistry. 342, 1, p. 103-110 8 p.

Research output: Contribution to journalArticle

5 Scopus citations

Double-cuvette ISES: In situ estimation of enantioselectivity and relative rate for catalyst screening

Dey, S., Karukurichi, K. R., Shen, W. & Berkowitz, D. B., Jun 22 2005, In : Journal of the American Chemical Society. 127, 24, p. 8610-8611 2 p.

Research output: Contribution to journalArticle

41 Scopus citations
2004

Following an ISES lead: The first examples of asymmetric Ni(0)-mediated allylic amination

Berkowitz, D. B. & Maiti, G., Aug 5 2004, In : Organic Letters. 6, 16, p. 2661-2664 4 p.

Research output: Contribution to journalArticle

65 Scopus citations

In situ enzymatic screening (ISES) of P,N-ligands for Ni(0)-mediated asymmetric intramolecular allylic amination

Berkowitz, D. B., Shen, W. & Maiti, G., Sep 20 2004, In : Tetrahedron Asymmetry. 15, 18, p. 2845-2851 7 p.

Research output: Contribution to journalArticle

18 Scopus citations

Mono- and bivalent ligands bearing mannose 6-phosphate (M6P) surrogates: Targeting the M6P/ insulin-like growth factor II receptor

Berkowitz, D. B., Maiti, G., Charette, B. D., Dreis, C. D. & MacDonald, R. G., Dec 23 2004, In : Organic Letters. 6, 26, p. 4921-4924 4 p.

Research output: Contribution to journalArticle

41 Scopus citations

Synthesis of quaternary amino acids bearing a (2′Z)-fluorovinyl α-branch: Potential PLP enzyme inactivators

Berkowitz, D. B., De La Salud-Bea, R. & Jahng, W. J., May 27 2004, In : Organic Letters. 6, 11, p. 1821-1824 4 p.

Research output: Contribution to journalArticle

34 Scopus citations
2003

Structure-Activity Analysis of Guanidine Group in Agmatine for Brain Agmatinase

Huang, M. J., Regunathan, S., Botta, M., Lee, K., McClendon, E., Yi, G. B., Pedersen, M. L., Berkowitz, D. B., Wang, G., Travagli, M. & Piletz, J. E., 2003, In : Annals of the New York Academy of Sciences. 1009, p. 52-63 12 p.

Research output: Contribution to journalArticle

13 Scopus citations
2002

In situ enzymatic screening (ISES): A tool for catalyst discovery and reaction development

Berkowitz, D. B., Bose, M. & Choi, S., May 3 2002, In : Angewandte Chemie - International Edition. 41, 9, p. 1603-1607 5 p.

Research output: Contribution to journalArticle

35 Scopus citations
2001

(α-Monofluoroalkyl)phosphonates: A class of isoacidic and "tunable" mimics of biological phosphates

Berkowitz, D. B. & Bose, M., 2001, In : Journal of Fluorine Chemistry. 112, 1, p. 13-33 21 p.

Research output: Contribution to journalArticle

125 Scopus citations

A Convergent Triflate Displacement Approach to (α-Monofluoroalkyl)phosphonates

Berkowitz, D. B., Bose, M. & Asher, N. G., Jun 28 2001, In : Organic Letters. 3, 13, p. 2009-2012 4 p.

Research output: Contribution to journalArticle

30 Scopus citations

Stereocontrolled synthesis of quaternary β,γ-unsaturated amino acids: Chain extension of D- and L-α-(2-tributylstannyl)vinyl amino acids

Berkowitz, D. B., Chisowa, E. & McFadden, J. M., Jul 23 2001, In : Tetrahedron. 57, 30, p. 6329-6343 15 p.

Research output: Contribution to journalArticle

39 Scopus citations
2000

Engineering acyclic stereocontrol in the alkylation of vinylglycine- derived dianions: Asymmetric synthesis of higher α-vinyl amino acids

Berkowitz, D. B., McFadden, J. M. & Sloss, M. K., May 19 2000, In : Journal of Organic Chemistry. 65, 10, p. 2907-2918 12 p.

Research output: Contribution to journalArticle

47 Scopus citations

Enzyme-assisted asymmetric total synthesis of (-)-podophyllotoxin and (- )-picropodophyllin

Berkowitz, D. B., Choi, S. & Maeng, J. H., Feb 11 2000, In : Journal of Organic Chemistry. 65, 3, p. 847-860 14 p.

Research output: Contribution to journalArticle

86 Scopus citations

Novel "reverse Kahne-type glycosylation": Access to O-, N-, and C-linked epipodophyllotoxin conjugates

Berkowitz, D. B., Choi, S., Bhuniya, D. & Shoemaker, R. K., Apr 20 2000, In : Organic Letters. 2, 8, p. 1149-1152 4 p.

Research output: Contribution to journalArticle

16 Scopus citations

α-Fluorinated phosphonates as substrate mimics for glucose 6-phosphate dehydrogenase: The CHF stereochemistry matters

Berkowitz, D. B., Bose, M., Pfannenstiel, T. J. & Doukov, T., Jul 28 2000, In : Journal of Organic Chemistry. 65, 15, p. 4498-4508 11 p.

Research output: Contribution to journalArticle

110 Scopus citations
1999

Facile installation of the phosphonate and (α,α- difluoromethyl)phosphonate functionalities equipped with benzyl protection

Berkowitz, D. B., Bhuniya, D. & Peris, G., Mar 5 1999, In : Tetrahedron Letters. 40, 10, p. 1869-1872 4 p.

Research output: Contribution to journalArticle

40 Scopus citations

Hydrolytic enzymatic transformation of advanced synthetic intermediates: On the choice of the organic cosolvent

Berkowitz, D. B., Hartung, R. E. & Choi, S., Dec 3 1999, In : Tetrahedron Asymmetry. 10, 23, p. 4513-4520 8 p.

Research output: Contribution to journalArticle

12 Scopus citations
1996

A convenient synthesis of L-α-vinylglycine from L-homoserine lactone

Berkowitz, D. B. & Smith, M. K., 1996, In : Synthesis. 1, p. 39-41 3 p.

Research output: Contribution to journalArticle

30 Scopus citations

Chemoenzymatic and ring E-molecular approach to the (-)-podophyllotoxin skeleton. Synthesis of 3',4',5'-tridemethoxy-(-)-podophyllotoxin

Berkowitz, D. B., Maeng, J. H., Dantzig, A. H., Shepard, R. L. & Norman, B. H., Oct 2 1996, In : Journal of the American Chemical Society. 118, 39, p. 9426-9427 2 p.

Research output: Contribution to journalArticle

34 Scopus citations
16 Scopus citations
125 Scopus citations

Synthesis of higher α-chlorovinyl and α-bromovinyl amino acids: The amino protecting group determines the reaction course

Berkowitz, D. B., Pedersen, M. L. & Jahng, W. J., Jun 17 1996, In : Tetrahedron Letters. 37, 25, p. 4309-4312 4 p.

Research output: Contribution to journalArticle

13 Scopus citations

α-Vinyllysine and α-vinylarginine are time-dependent inhibitors of their cognate decarboxylases

Berkowitz, D. B., Jahng, W. J. & Pedersen, M. L., Sep 17 1996, In : Bioorganic and Medicinal Chemistry Letters. 6, 18, p. 2151-2156 6 p.

Research output: Contribution to journalArticle

33 Scopus citations
1995
61 Scopus citations