Chemistry and Biochemistry
Dipl. Brew. - Institute of Brewing and Distilling (UK)
Ph.D. (Organic Chemistry) - Texas Tech University, Lubbock TX
M.S. (Organic Chemistry) - Dartmouth College, Hanover NH
B.S. (Chemistry-ACS approved) - University of Idaho, Moscow ID
ISO-1, an inhibitor of the proinflammatory cytokine MIF, has been shown to exhibit preventative properties toward Type 1 Diabetes in transgenic mice. We have shown that this compound, and derivatives, can be prepared by the intra-molecular cyclization of a beta,gamma-unsaturated oxime. The reaction utilizes a palladium(II) catalyst to effect the cyclization, and depending upon the specific ligands employed, can result in modest stereocontrol of the reaction. Recent studies in our laboratory have shown that palladium(0) can mediate a tandem intra-molecular cyclization / aryl coupling. We are currently exploring the cyclization of alpha,beta-unsaturated oximes and the use of other metals to affect the cyclizations.
In other work, our group is exploring the intercalative properties of O-substituted N-acridinyl hydroxylamines. These compounds are based on the successful antitumor agent m-amsacrine (m-AMSA). The major issue with m-amsacrine involves the rapid hydrolysis/thiolysis in vivo. The use of the hydroxylamino group appears to inhibit that decomposition pathway. Our target compounds are prepared by synthesis of an O-substituted hydroxylamine and then its coupling with 9-chloroacridine. The results of an initial study indicate that these compounds are effective DNA intercalators with acceptable LD50 values toward glioblastoma cell lines. Further work in this area will involve exploration of the kinetics of hydrolysis of these compounds, evaluation of the specific interactions during intercalation, and modification of the O-substituted compounds to enhance biological activity.
In addition to our work in heterocyclic chemistry, we have begun exploring two major areas of research in beer brewing. The first of these projects involves the exploration of the mechanism of hop acid isomerization. Initial work in this area indicates that the isomerization is magnesium catalyzed. We are currently determining the binding constant and location of binding for the magnesium cation in that process. The second of the projects involves the use of spectroscopic techniques for the analysis of components in beer. For example, we have recently shown that we can accurately measure alcohol and carbon dioxide content using mid-range FTIR.
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