Department of Chemistry & Biochemistry Faculty
Dr. Peter de Lijser
Professor Organic Chemistry
Phone: (657) 278-3290
Phone: (657) 278-5274
CHEM 115 Introduction to General Chemistry
CHEM 200 Chemistry for Nursing and Allied Health Professionals
CHEM 301A/B Organic Chemistry
CHEM 302 Organic Chemistry Laboratory
CHEM 313 A-C Environmental Pollution and Solutions
CHEM 431 Advanced Organic Chemistry
CHEM 505A/B Seminar
CHEM 537 Organic Spectroscopy
Postdoctoral University of Rochester, Rochester, NY
Ph.D. Dalhousie University; Halifax Nova Scotia, Canada
M.Sc. Leiden University; Leiden, Netherlands
B.Sc. Van Leeuwenhoek Institute; Delft, Netherlands
Research in the de Lijser group is two-fold. We use physical organic techniques to study the reactive intermediates formed in the enzymatic and photooxidative processes of xenobiotic compounds used as drugs and pesticides (mostly those with oxime and oxime ether functionalities). The reactive intermediates are generated by thermal and photochemical techniques. Molecules of interest are synthesized, purified and characterized. The chemistry of the reactive intermediates is explored by laser flash photolysis and steady state photolysis experiments. Products are analyzed by gas chromatography, mass spectrometry and NMR techniques. We have shown that several different reactive intermediates are involved in the electron transfer reactions of oximes and oxime ethers. Current research interests are geared towards learning more about the specific reactivities of the different reactive intermediates, including iminoyl and iminoxyl radicals, in order to be able to exploit them in different processes.
In a collaborative project with Dr. Nilay Patel (Department of Biological Science, CSUF) we design and synthesize small organic molecules that can be used to maintain the pluripotency of stem cells. The goal of this collaboration is to design and synthesize drugs that can be used to block two proteins from interacting with one another and thereby promoting pluripotency in stem cells. The desired molecules are designed by molecular modeling and synthesized in the laboratory. A secondary goal is to perform a structure-reactivity study on a series of drugs in which only one small change occurs. We are currently focusing on several different classes of molecules (chalcones, amides, small peptides, carboxylic acids and esters), some of which have shown promising results in biological studies carried out by our collaborators in the Department of Biological Science at CSUF.
de Lijser Group Activities
March 2011: Peter de Lijser and three of his research students, Luke Hanna (B.S. Biology and B.S. Biochemistry, Spring 2009), and current graduate students Lisa Hoong and Kevin Chen attended the 241st Spring Meeting of the American Chemical Society in Anaheim to present the following posters:
- Peter de Lijser, with co-authors: Hang Do (graduate student), Chelsea Roush (undergraduate), Colin Bennett (former HHMI summer undergraduate research student). "Intramolecular Trapping of Iminoxyl Radicals with Olefins"
- Luke Hanna, with co-authors: Kwanruthai Tadpetch (former M.S. student; currently in PhD program at UCI), and Lalisa Stutts (former undergraduate student, currently in PhD program at UCI). "Mechanistic studies of an unusual rearrangement of iminoxyl radicals derived from benzylketoximes"
- Lisa Hoong. "Mechanistic studies of radicals and radical ions generated in the oxidation of N-hydroxy and N-alkoxyimines"
- Kevin Chen, with co-authors Dr. Nilay Patel, Melchor Alcantara (B.S. Biochemistry, Fall 2010), Edward Laguna (current undergraduate student), and biology students Leslie Kirby, Brenda Noble, Tyler Routledge and Jason Schott. "Design and synthesis of benzyl ether and benzylamine derivatives for use as Wnt mimetics to promote pluripotency of stem cells"
“Highly Efficient Formation of Nitriles and Alkoxy Radicals From N-Alkoxyiminoyl Radicals in Solution”, de Lijser, H.J.P.; Burke, C.R.; Rosenberg, J.; Hunter, J. J. Org. Chem., 2009, 74, 1679-1684.
“Mechanistic Aspects of the Formation of Aldehydes and Nitriles in Photosensitized Reactions of Aldoxime Ethers”, de Lijser, H. J. P.; Rangel, N. A.‡; Tetalman, M.‡; Tsai, C. K. J. Org. Chem., 2007, 72, 4126-4134.
“Effect of Structure in Benzaldehyde Oximes on the Formation of Aldehydes and Nitriles Under Photoinduced Electron Transfer Conditions”, de Lijser, H. J. P.; Hsu, S.‡; Marquez, B. V.‡; Park, A.‡; Sanguantrakun, N.; Sawyer, J. R.‡ J. Org. Chem., 2006, 71, 7785-7792.
“Quinone-Sensitized Steady-State Photolysis of Acetophenone Oximes Under Aerobic Conditions: Kinetics and Product Studies”, Park, A.‡; Kosareff, N. M.‡; Kim, J. S.; de Lijser, H. J. P. Photochem. Photobiol., 2006, 82, 110-118.
“Photochemical Acetalization of Carbonyl Compounds in Protic Media Using an in Situ Generated Photocatalyst”, de Lijser, H. J. P.; Rangel, N. A.‡ J. Org. Chem., 2004, 69, 8315-8322.
“Photosensitized Reactions of Oxime Ethers. A Steady-State and Laser Flash Photolysis Study”, de Lijser, H. J. P.; Tsai, C. K. J. Org. Chem., 2004, 69, 3057-3067.
“Preparation and Structure of an Unexpected Dehydrogenation Product from 2,6-Diphenylcyclohexanone Oxime”, de Lijser, H. J. P.; Dedeian, C. E.‡; Sawyer, J. R.‡; Herron, S. R.; Kantardjieff, K. A. J. Chem. Cryst., 2004, 34, 103-110.
“Substituent Effects in Oxime Radical Cations. 1. Photosensitized Reactions of Acetophenone Oximes”, de Lijser, H. J. P.; Kim, J. S.; McGrorty, S. M.‡; Ulloa, E. M.‡ Can. J. Chem., 2003, 81, 575-585.
“Photosensitized Regeneration of Carbonyl Compounds From Oximes”, de Lijser, H. J. P.; Fardoun, F. H.; Sawyer, J. R.‡; Quant, M.‡ Org. Lett., 2002, 4, 2325-2328.
(‡ = undergraduate co-author)