David L. Van Vranken

picture of David L. Van Vranken

Professor of Chemistry
School of Physical Sciences
Associate Dean
School of Physical Sciences

Ph.D., Stanford University, 1991, Chemistry


B.S., University of Texas at Austin, 1987, Chemistry

Phone: (949) 824-5455, 4678
Fax: (949) 824-8571
Email: dlvanvra@uci.edu

University of California, Irvine
FRH 2046D
University of California
Mail Code: 2025
Irvine, CA 92697
Research Interests
organic synthesis, chemical mechanism, chemical reactivity, synthetic methodology
URL
Academic Distinctions
National Science Foundation Graduate Fellow
National Science Foundation Postdoctoral Fellow
Camille and Henry Dreyfus Foundation New Faculty Award
National Science Foundation CAREER Award
Glaxo Wellcome Chemistry Scholar
Eli Lilly Faculty Grantee
Alfred P. Sloan Research Fellow
2000 Arthur C. Cope Scholar
Class of 2005 Outstanding Professor Award - School of Physical Sciences, 2005
School of Physical Sciences Award for Outstanding Contributions to Undergraduate Education, 2007
Appointments
1991 - 1994 University of California at Berkeley, Postdoc
Research Abstract
The Van Vranken group studies and develops chemical reactions and applies them to synthetic problems.

Our efforts to harness these patterns of reactivity have led to new tools for biology, new tools for synthesis, and new approaches to construction of natural products. Our group has developed concise routes to a range of bioactive natural products that include: AT-2433 A1 and B1; tjipanazoles F1, F2, C1, and C2; phakellistatins 3 and 13; madindolines A and B; corylifolin; and bakuchiol.

We are broadly interested in chemical mechanism and chemical reactivity. We apply that knowledge to the synthesis of bioactive molecule and transition metal-catalyzed reactions that lead to insertion of carbon atoms of one atom at a time. We have shown that iron and palladium catalysts can catalyze the addition and rearangment of carbenes, derived from diazo compounds, to allylic and propargylic thioethers. We have extended this work into powerful new reactions including carbenylative cross-coupling reactions, carbenylative amination, and carbenylative alkylation.
Publications
Fooshee, D.; Mood, A.; Gutman, E.; Tavakoli, M.; Urban, G.; Liu, F.; Huynh, N.; Van Vranken, D.; Baldi, P. (2018) Deep learning for chemical reaction prediction Mol. Sys. Des. Eng. 2018, 3, 442-452.
 
Arredondo, V. A.; Hiew, S. C.; Gutman, E. S.; Premachandra, I. D. U. A.; Van Vranken, D. L. (2017) Enantioselective Palladium-Catalyzed Carbene Insertion into the N-H Bonds of Aromatic Heterocycles. Angew. Chem. Int. Ed. 56, 4156 –4159.
 
Arredondo, V. A.; Van Vranken, D. L. (2017) “80. ¿Es posible una vida basada en el silicio?” in Ciencia, y además lo entiendo!!! (Science, and I also understand it!!!) Ed. Guerrido, Q.
 
Mood, A. D.; Premachandra, I. D. U. A.; Hiew, S. C.; Wang, F.-Q.; Scott, K. A.; Oldenhuis, N. J.; Liu, H.; Van Vranken, D. L. (2017) Potent Antifungal Synergy of Phthalazinone and Isoquinolones with Azoles Against Candida albicans. ACS Med. Chem. Lett. 8, 168-173.
 
Premachandra, I. D. U. A.; Nguyen, T.; Shen, C.; Gutman, E.; Van Vranken, D. L. (2015) Carbenylative Amination and Alkylation of Vinyl Iodides via Palladium Alkylidene Intermediates. Org. Lett. 17, 5464-5467.
 
Premachandra, I. D. U. A.; Scott, K. A.; Shen, C.; Wang, F.-Q.; Lane, S.; Liu, H.; Van Vranken, D. L. (2015) Potent Synergy between Spirocyclic Pyrrolidinoindolinones and Fluconazole against Candida albicans. ChemMedChem. 10, 1672-1686.
 
Kitamura, M.; Yuasa, R; Van Vranken, D. L. (2014). Synthesis of the Cyclic Prenylguanidine Nitensidine E using a Palladium-Catalyzed Carbenylative Amination. Tetrahedron Lett. 56, 3027-3031.
 
Gutman, E. S.; Arredondo, V.; Van Vranken, D. L. (2014). Cyclization of ?3-Benzylpalladium Intermediates Derived from Carbene Insertion. Org. Lett. 16, 5498–5501.
 
Khanna, A.; Premachandra, I. D. U. A.; Sung, P. D.; Van Vranken, D. L. (2013). Palladium-Catalyzed Catellani Aminocyclopropanation Reactions with Vinyl Halides. Org. Lett. 15, 3158-3161.
 
Van Vranken, D. L.; Weiss, G. A. Introduction to Bioorganic Chemistry and Chemical Biology. Garland Science: New York, 2012.
 
Khanna, A.; Maung, C.; Johnson, K. R.; Luong, T. T.; Van Vranken, D. L. (2012). Carbenylative Amination with N-Tosylhydrazones. Org. Lett. 14, 3233-3235.
 
Khanna, A.; Premachandra, I. D. U. A.; Sung, P. D.; Van Vranken, D. L. (2013). Palladium-Catalyzed Bis-cyclization/Dimerization Reactions of omega-Aminovinyl Halides. Org. Lett. 15, 3694-3697.
 
Kudirka, R.; Devine, S. K. J.; Adams, C. S.; Van Vranken, D. L. (2009). Palladium-Catalyzed Insertion of alpha-Diazoesters into Vinyl Halides to Generate alpha,beta-Unsaturated-gamma-Amino Esters. Angew. Chem. Int. Ed. 10, 726-731.
 
Juskowiak, G. L., II, McGee, C. J., Greaves, J., Van Vranken, D. L. (2008). Synthesis, Screening, and Sequencing of Cysteine-Rich One-Bead One-Compound Peptide Libraries. J. Comb. Chem. 10, 726-731.
 
Devine, S. K. J., Van Vranken, D. L. (2008). Palladium-Catalyzed Carbene Insertion and Trapping with Carbon Nucleophiles. Organic Letters, 10(10), 1909-1911.
 
Kudirka, R., Van Vranken, D. L. (2008). Palladium-Catalyzed Cyclization Reactions Involving Palladium-Catalyzed Carbene Insertion into Aryl Halides. Journal of Organic Chemistry, 73(9), 3585-3588.
 
Devine, S. K., Van Vranken, D. L. (2007). Palladium-Catalyzed Carbene Insertion into Vinyl Halides and Trapping with Amines. Org. Lett., 9, 2047-2049.
 
Fernandes, N., Bailey, D. E., Van Vranken, D. L., Allbritton, N. L. (2007) Use of Docking Peptides to Design Modular Substrates with High Efficiency for Mitogen-Activated Protein Kinase Extracellular Signal-Regulated Kinase. ACS Chemical Biology, 2(10), 665–673.
 
Zhang, C., Albermann, C., Gu, X., Peters, N. R., Chisholm, J. D., Gilbert, E. J., Van Vranken, D. L., Thorson, J. (2006). RebG and RebM-Catalyzed Indolocarbazole Diversification. ChemBiochem, 7, 795-804.
 
Bacci, J. P., Kearney, A. M., Van Vranken, D. L. (2005). Efficient Two-Step Synthesis of 9-Aryl-6-hydroxy-3H-xanthen-3-one Fluorophores. J. Org. Chem., 70, 9051-9053.
 
Saleh, A. Z., Greenman, K. L., Billings, S., Van Vranken, D. L., Krolewski, J. J. (2005). Binding of Madindoline A to the Extracellular Domain of gp130. Biochemistry, 44, 10822-10827.
 
Greenman, K. L., Van Vranken, D. L. (2005). Palladium-Catalyzed Carbene Insertion into Benzyl Bromides. Tetrahedron, 61, 6438-6441.
 
Greenman, K. L., Hach, D. M., Van Vranken, D. L. (2004). Synthesis of Phakellistatin 13 and Oxidation to Phakellistatin 3 and Isophakellistatin 3. Org. Lett., 6, 1713-1716.
 
Juskowiak, G. L., Stachel, S. J., Tivitmahaisoon, P., Van Vranken, D. L. (2004). Fluorogenic Peptide Sequences - Transformation of Short Peptides into Fluorophores Under Ambient Photooxidative Conditions. J. Am. Chem. Soc., 126, 550-556.
 
McComas, C. C., Van Vranken, D. L. (2003). Application of Chiral Lithium Amide Bases to the Thia-Sommelet Dearomatization Reaction. Tetrahedron Lett., 44/45, 8203-8205.
 
Yoburn, J. C., Van Vranken, D. L. (2003). Synthesis of Dityrosine Cross-Linked Peptide Dimers Using the Miyaura-Suzuki Reaction. Org. Lett., 5, 2817-2820.
 
Bacci, J., Greenman, K. L., Van Vranken, D. L. (2003). Iron(II)-Catalyzed Sulfimidation and [2,3]-Sigmatropic Rearrangement of Propargyl Sulfides with t-Butoxycarbonylazide. Access to N-Allenylsulfenimides. J. Org. Chem., 68, 4955-4958.
 
Yoburn, J. C., Tian, W., Brower, J. O., Nowick, J. S., Glabe, C. G., Van Vranken, D. L. (2003). Dityrosine Crosslinked Aß Peptides: Fibrillar Beta Structure in A((1-40) is Conducive to Formation of Dityrosine Crosslinks, but a Dityrosine Crosslink in A((8-14) does not Induce Beta Structure. Chem. Res. Toxicol., 16, 531-535.
 
Facompre, M., Carrasco, C., Vezin, H., Chisholm, J. D., Yoburn, J. C., Van Vranken, D. L., Bailly, C. (2003). Indolocarbazole Glycosides in Inactive Conformations. ChemBiochem, 4, 386-395.
 
Yoburn, J. C., Deb, S., Manfield, I. W., Stockley, P. G., Van Vranken, D. L. (2003). A Biaryl Peptide Crosslink in a MetJ Peptide Model Confers Cooperative, Nonspecific Binding to DNA that Ablates both Repressor Binding and in vitro Transcription. Bioorg. Med. Chem., 11, 811-816.
 
Facompre, M., Carrasco, C., Colson, P., Houssier, C., Chisholm, J. D., Van Vranken, D. L., Bailly, C. (2002). DNA binding and topoisomerase I poisoning activities of novel disaccharide indolocarbazoles. Molecular Pharmacol., 62, 1215-1227.
 
Perales, J. B., Makino, F. N., Van Vranken, D. L. (2002). Convergent Stereocontrol in Peterson Olefinations. Application to the Synthesis of (±)-3-Hydroxybakuchiol and Corylifolin. J. Org. Chem, 67, 6711-6717.
 
Presley Bodnar, A. L., Gilbert, E. J., Yoburn, J. C., Van Vranken, D. L. (2002). Synthesis and Study of a Gramicidin B Mutant Possessing a Ditryptophan Crosslink. J. Peptide Sci., 8, 510-520.
 
McComas, C. C., Perales, J. B., Van Vranken, D. L. (2002). Synthesis of (±)-Madindolines and Chemical Models. Studies of Chemical Reactivity. Org. Lett., 4, 2337-2340.
 
Matthews, J. H., Dinh, T. D., Tivitmahaisoon, P., Ziller, J. W., Van Vranken, D. L. (2001). Intramolecular Ditryptophan Crosslinks Enforce Two Types of Antiparallel Beta Structures. Chemistry & Biology, 8, 1071-1079.
 
Carrasco, C., Facompré, M., Chisholm, J. D., Van Vranken, D. L., Wilson, D. W., Bailly, C. (2002). DNA sequence recognition by the indolocarbazole antitumor antibiotic AT2433-B1 and its diastereoisomer. Nuc. Acids Res., 30, 1774-1781.
 
Van Vranken, D. L. (2004). Polychlorinated biphenyls inhibit amyloid fibril formation. Chemistry & Biology, 11, 1604-1606.
Professional Society
American Chemical Society
Other Experience
Intern, Surface Analysis (X-ray Photoelectron Spectroscopy)
IBM Corporation 1985—1986

Postdoc - Bioorganic Chemistry
University of California, Berkeley 1991—1994

Graduate Programs
Chemistry

Last updated
10/24/2018