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Gronert, Scott

Department chair Professor Organic and biological/biophysical chemistry Oliver Hall 3041/0 (804) 828-2753 sgronert@vcu.edu

Education
B.S., California State University, Long Beach, 1983
Ph.D., University of California, Berkeley, 1987
Postdoctoral, University of Colorado, 1987-90

Research interests
Research in the Gronert group focuses on using mass spectrometry and computational chemistry to investigate problems in organic and biological chemistry. Both of these techniques are evolving rapidly and proving to be two of the most powerful tools in modern chemistry.  

Gas-phase reaction mechanisms
Although the great majority of organic chemistry is carried out in solution, the gas-phase provides many advantages in probing reaction mechanisms. First, it is possible to study reactions in a well-characterized, inert environment and probe intermediates that are too reactive to isolate or characterize in solution. Second, in the absence of solvation and ion pairing effects, it is possible to investigate the intrinsic reaction mechanism and confidently attribute reactivity trends to the characteristics of the reaction partners. Moreover, differences between gas-phase and solution reactions offer important insights into the role of solvent in the reaction mechanism. Current projects focus on substitution vs. elimination reactions, chiral recognition in small molecular clusters, and oxidation mechanisms involving metal-centered catalysts.

Protein post-translational modifications
Post-translational protein modifications, such as phosphorylation and glycosylation, play a major role in signaling and other cellular activities, but remain a major challenge in modern bioanalytical chemistry. They are not coded by DNA, often are found in low concentrations and can be transient. Mass spectrometry and proteomics approaches have proven to be the prime tools for identifying and characterizing post-translational protein modifications. We are focusing our efforts on the identification of protein oxidation products related to aging and diabetes. In each case, cellular oxidative stress leads to irreversible protein modifications. In aging, protein carbonyls are formed and reach high concentrations late in life. In diabetes, hyperglycemia combined with oxidative stress eventually leads to advanced glycation end-products, a protein modification linked to several diseases. In our work, we are developing methods to identity the specific site and extent of the protein modification. Our approach involves selective labeling of the modification site followed by a proteomics analysis using mass spectrometry.

References

Fournier, F.; Afonso, C.; Fagin, A.E.; Gronert, S.; Tabet, J.C., Can Cluster Structure Affect Kinetic Method Measurements? The Curious Case of Glutamic Acid’s Gas-Phase Acidity. Journal of The American Society for Mass Spectrometry 2008, 19, 1887-1896.

Wong, F.M.; Capule, C.C.; Chen, D.X.; Gronert, S.; Wu, W.M., Surprisingly low aqueous acidity at the alpha-positions of pyridiniums and pyrimidinium: The role of solvation. Organic Letters 2008, 10, 2757-2760.

Fagin, A.E.; Wang, G.; Lau, M.C.; Gronert, S., Gas-phase stereloselective binding to Mn/salen catalysts. Organic Letters 2008, 10, 1771-1773.

Gronert, S., An epoxide intermediate in nucleophilic acylations by thiazolium precursors. Organic Letters 2007, 9, 3065-3068.

Gronert, S.; Keeffe, J.R., The protonation of allene and some heteroallenes, a computational study. Journal of Organic Chemistry 2007, 72, 6343-6352.

Gronert, S., EPR data do not indicate that hyperconjugation stabilizes alkyl radicals. Organic Letters 2007, 9, 2211-2214.

Selected publications

Updated October 2010

Koehn, S. K.; Gronert, S.; Aldajaei, J. T. “Mechanistic Insights into the Reactions of Co(III) salens with Diazoacetates”, Org. Lett. 2010, 12, 676-679.

Koehn, S.; Tran, N. L.; Gronert, S.; Wu, W. “The Stability of Aryl Carbanions Derived from Pyridine N-Oxide: The Role of Resonance in Stabilizing Aryl Anions”, J. Am. Chem. Soc., 2010, 132, 390-395.

Gronert, S.; Keeffe, J. R.; O’Ferrall, R. A. M., Correlations between Carbene and Carbenium Stability: Ab Initio Calculations on Substituted Phenylearbenes, Nonbenzenoid Arylearbenes, Heteroatom-Substituted Carbenes, and the Corresponding Carbocations and Hydrogenation Products J. Org. Chem. 2009, 74, 5250-5259.

Gronert, S.; Simpson, D. C.; Conner, K. M. “A Reevaluation of Computed Proton Affinities for the Common alpha-Amino Acids”, J. Am. Soc. Mass Spectrom. 2009, 20, 2116-2123.

Gronert, S. “The Folly of Protobranching: Turning Repulsive Interactions into Attractive Ones and Rewriting the Strain/Stabilization Energies of Organic Chemistry.” Chem. Eur. J., 2009, 15, 5372-5382.

Fournier, F.; Afonso, Fagin, A. E.; Gronert, S.; Tabet, J. C. “Can Cluster Structure Affect Kinetic Method Measurements? The Curious Case of Glutamic Acid’s Gas-Phase Acidity”, J. Am. Soc. Mass Spectrum. 2008 19, 1887-1896.

Wong, F. M., Capule, C. C. Chen, D. X., Gronert, S. Wu, W. M. “Surprisingly low aqueous acidity at the alpha-positions of pyridiniums and pyrimidinium: The role of solvation”, Org. Lett. 2008, 10, 2557-2760.

Fagin, A. E.; Wang, G.; Lau, M. C.; Gronert, S. “Gas-Phase Stereoselective Binding to Mn/Salen Catalysts” Org. Lett. 2008, 10, 1771-1773.

Gronert, S., An epoxide intermediate in nucleophilic acylations by thiazolium precursors. Organic Letters 2007, 9, 3065-3068.

Gronert, S.; Keeffe, J.R., The protonation of allene and some heteroallenes, a computational study. Journal of Organic Chemistry 2007, 72, 6343-6352.

Gronert, S., EPR data do not indicate that hyperconjugation stabilizes alkyl radicals. Organic Letters 2007, 9, 2211-2214.

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