Skip to content. | Skip to navigation

Sections
Personal tools
You are here: Home > Research

Research

by brianadmin last modified Feb 07, 2017 12:48 PM

Research Projects

Synthesis and Properties of Sterically Congested Amino Acids

There are twenty or so naturally occurring amino acids that are the building blocks of proteins.  My research group works to prepare and study novel analogs of these molecules that are not found in nature.  In particular, we synthesize sterically congested alpha,alpha-disubstituted alpha-amino acids, which are much bulkier than their natural relatives.  This extra bulk affects their properties and the properties of peptides (chains of amino acids) that incorporate them.  An example is shown below for the synthesis of alpha-methylcysteine.  The enzyme porcine liver esterase (PLE) is used to stereoselectively hydrolyze one of the ester groups in the symmetrical malonate diester (1).  The resulting carboxylic acid (2) is then converted into a protected amino acid (3) by a Curtius rearrangement followed by treatment with an alcohol.  Current work in the group is aimed at expanding the scope of this method to access a wider range of analogs.

kedrowski research1

Congested Amino Acid Publications (undergraduate coauthors are underlined). 

  • Kedrowski, B. L.; Gutow, J. H.; Stock, G.; Smith, M.; Jordan, C.; Masterson, D. S. “Glutathione Reductase Activity With an Oxidized Methylated Glutathione Analog” Journal of Enzyme Inhibition and Medicinal Chemistry201429(4), 491-494.

  • Masterson, D. S.; Kedrowski, B. L.; Blair, A. “An Improved Protocol for the Preparation of Protected (R)-2-Methylcysteine and its Use in Solution Phase Synthesis of a Glutathione Analogue” Synlett2010, 19, 2941-2943.

  • Kedrowski, B. L. "Synthesis of Orthogonally Protected (R)- and (S)-2-Methylcysteine via an Enzymatic Desymmetrization and Curtius RearrangementJournal of Organic Chemistry, 2003, 68, 5403-5406.

     

Ring Forming Reactions of Quinones and Ynamides

Quinones and ynamides are versatile functional groups that have proven useful for constructing rings in organic chemistry.  I am interested in discovering new ways to build rings with these molecules and expand their utility in organic synthesis. 

Quinone and Ynamide Publications (undergraduate coauthors are underlined). 

  • Wang, X. -N.; Yeom, H. -S; Fang, L. -C.; He, S.; Ma, Z. -X.; Kedrowski, B. L.; Hsung, R. P. “Ynamides in Ring Forming Transformations” Accounts of Chemical Research201447, 560-578.

  • Kedrowski, B. L.Hoppe, R. “A Concise Synthesis of (±)-Cacalol” Journal of Organic Chemistry, 2008, 73, 5177-5179.

     

Archeological Lipid Residue Analysis

Another research interest involves using gas chromatography/mass spectrometry GC/MS to analyze lipid residues in archaeological hearth sites.  This project is a collaboration between myself and Drs. Jeffery Behm and Barbara Crass from the Department of Anthropology and Religious Studies at UW Oshkosh, and Dr. Charles Holmes from the University of Alaska Anchorage.  Their study of the Swan Point archaeological site in central Alaska uncovered ancient hearths containing lipid residues dating to the late Pleistocene period.  In my research group we extract soil samples, derivative them, and analyze them by GC/MS to establish lipid fingerprints of the samples that shed light on the source of these fats and increase our understanding of the lives of these early northern peoples.  Recent work on this project has focused on simulated weathering model hearth lipid systems.  The goal of this work is to study how lipid mixtures from simulated hearth charge over time.

Archaeochemistry Publications (undergraduate coauthors are underlined)

  • Crass B. A.; Kedrowski B. L.; Baus, J.; Behm, J. A. “Residue Analysis of Bone Fueled Pleistocene Hearths” In: From The Yenisei To The Yukon: Interpreting Lithic Assemblage Variability In Late Pleistocene/Early Holocene Beringia; Goebel, T., Buvit, I., Eds.; Texas A&M University Press: College Station, Texas, 2011; p 192.

  • Kedrowski, B. L.; Crass, B. A.; Behm, J. A.;  Luetke, J. C.Nichols, A. L.Moreck, A. M.; Holmes, C. E. “GC-MS Analysis of Fatty Acids From Ancient Hearth Residues at the Swan Point Archaeological Site” Archaeometry2009,51, 110-122.

 

Isolation, Characterization, and Properties of Seed Meal Compounds

Seed meals are the solid materials left over after seeds have been pressed for their oil.  These materials represent a rich source of interesting biomolecules with potentially useful properties. Potential applications for the materials include use as antimicrobial agents and in skin care.  This project involves extracting the seed meals, characterizing their extracts using High Performance Liquid Chromatography (HPLC) and mass spectrometry, and then testing their activity in bioassays. Recently my research group has been studying the ability of extracts derived from fruit seed meals to inhibit tyrosinase enzyme, which plays a key role in the synthesis of the skin pigment melamine. Possible applications of the these materials include uses as skin lightening and skin tone evening agents.  Previous work with virologist Dr. Teri Shors (Dept. of Biology, UW Oshkosh) identified anti-viral activity in some of these materials.   This project is being carried out in collaboration with the Wisconsin company Botanic Innovations (Spooner, WI) and with WiSys Technology Foundation.

 

Chemical Education

I am also interested in research in chemical education that involves developing new laboratory experiments, teaching materials, and pedagogies for organic chemistry instruction.  

ChemEd Publication

  • Kedrowski, B. L.; Wacholtz, W. F. “Thematic Use of Ribavirin as an Example to Illustrate NMR Principles and Techniques” In NMR Spectroscopy in the Undergraduate Curriculum: Upper-Level Courses and Across the Curriculum Volume 3; ACS Symposium Series 1225; Soulsby, D., Anna, L. J., Wallner, A. S., Eds. American Chemical Society: Washington, DC, 2016.

 

UWOImage
Document Actions
by brianadmin last modified Feb 07, 2017 12:48 PM