- B.S., 1959, University of Illinois
- Ph.D., 1963, Massachusetts Institute of Technology
- Alfred P. Sloan Fellow, 1970-1972
Areas of Specialization
Synthetic Organic Chemistry and the Development of New Reagents for Ultrasensitive Analysis of Bioactive Molecules
Organic chemistry: organic synthesis, natural products, highly strained ring systems, photochemistry and bioanalytical chemistry
Professor Carlson's research focuses primarily in the area of synthetic organic chemistry, new synthetic methods, strained-ring systems, photochemistry, natural products and bioanalytical chemistry.
As part of our effort to develop new synthetic methodology we have been investigating the chemistry of the highly strained methylenecyclopropane system as a building block of more complex molecules. We have developed methods by which the methylenecyclopropane group can be introduced into a variety of molecules by way of organometallic intermediates. Our most recent studies have involved the preparation of highly strained oxaspiropetanes by expoidation of substituted methylene-cyclopanes with dimethyldioxirane and an examination of their rearrangements with a variety of Lewis or protic acids. Some typical results are shown below:
In connection with work in the Center for BioAnalytical Research (CBAR) we have been engaged in an extensive program directed at the design and synthesis of new tagging reagents which will permit the detection and ultrasensitive quantitative analysis of bioactive molecules by fluorescent, chemiluminescent and electrochemical methods. This work involves extensive collaboration with chemists in other areas of chemistry. We have developed a series of substituted 2, 3- naphtahalenedicar-boxaldehyde reagents which react selectively with primary amines to give highly fluorescent derivatives. The imidazole substituted system shown is of current interest for laser-induced fluorescence detection in capillary electrophoresis studies.
The substituted hydroquinone reagent shown has been prepared and preliminary studies indicate that it will be very useful for electrochemical detection at very low levels.
Rose, M.J.; Lunte, S.M.; Carlson, R.G.; Stobaugh, J.F., "Hydroquinone-Based Derivatization Reagents for the Quantitation of Amines Using Electrochemical Detection," Anal. Chem., 1999, 71, 2221-2230.
Rose, M.J.; Lunte, S.M.; Audus, K.L.; Carlson, R.G.; Stobaugh, J.F., "Determination of Angiotensin II in Blood-Brain Barrie Permeability Studies Using Microbore LC with p-Nitorphenyl-2,5, -Dihydroxyphenylacetate bis-Tetrahydropranyl Ether as a Pre-Separation Electrochemical Labeling Reagent," Anal. Chim. Acta, 1999, 394, 299-308.
Synthesis and Chemiluminescence of a Protected Peroxyoxalate, Hohman, J.R.; Givens, R.S.; Carlson, R.G.; Orosz, G.; Tetrahedron Lett., 1996, 36, 8273-8276.
Physical and Biological Characteristics of the Antitumor Drug Actinomycin D Analogues Derivatized at the N-Methyl-L-valine Residues, Takusagawa, F; Wen,L.; Chu, W.; Li, Q; Takusagawa, K.; Carlson, R.G.; Weaver, R.F.; Biochemistry. 1996, 35, 13240-13249.
Cyclohexyl(2-methylene-cyclopropyl)carbinyl Carbocationic Rearrangements, J.E. Baldwin, Bonacorsi, R.G. Carlson, and F.D. Graber, J. Org. Chem., 58, 981 (1993).