Professor of Chemistry; Manager of Brewing Laboratory Science Program
Chemistry and Biochemistry
University of Northern Colorado
Campus Box 98
Greeley, CO 80639
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
Research/Areas of Interest
Novel Routes to 2-Isoxazolines and Related Heterocycles
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.
In other work, our group is exploring the intercalative properties of O-substituted
N-acridinyl hydroxylamines. These compounds are prepared by coupling the O-substituted
hydroxylamine with 9-chloroacridine. The results of an initial study indicate that
these compounds are effective DNA intercalators with biological activity (as measured
by MTT assay). 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 with 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. The second of the projects involves the
use of spectroscopic techniques for the analysis of components in beer. For example,
we have shown that %ABV can be rapidly analyzed by using ATR.
- “Palladium(0)-mediated cyclization of β,γ-unsaturated oximes”, Mikesell, J.; Mosher,
M.D., Tetrahedron Lett., 2016, 57, 1011-1013. doi: 10.1016/j.tetlet.2016.01.076
- “Introduction to Brewing Science Courses”, Mosher, M.D.; Trantham, K.W., in “Ethanol
and Education: Alcohol as a Theme for Teaching Chemistry” Barth, R., Benvenuto, M.A.
Eds., ACS Symposium Series; American Chemical Society: Washington, DC, 2015, 1189, 55-67. doi:10.1021/bk-2015-1189.ch005
- “Potential DNA bis-Intercalating Agents. Synthesis and Antitumor Activity of N,N'-(Methylenedi-4,1-cyclohexanediyl-bis(9-acridinamine)
Isomers”, Gribble, G.W.; Mosher, M.D.; Jaycox, G.D.; Cory, M.; Fairley, T.A. Heterocycles, 2014, 88(1), 535-546. doi: 10.3987/COM-13-S(S)77
- “Podcasting in Organic Chemistry”, Mosher, M.D., in “Advances in Teaching Organic
Chemistry”, Duffy-Matzner, J., Pacheco, K. Eds., ACS Symposium Series; American Chemical
Society: Washington, DC, 2012, 1108, 225-231. doi: 10.1021/bk-2012-1108.ch014
- “Non-cyclization routes to 2-Isoxazolines and 2-Isoxazoline N-oxides”, Mosher, M.D.
Curr. Org. Syn., 2011, 8(5), 645-658.
- “Organic Mastery: an activity for the undergraduate classroom”, Mosher, M.D.; Mosher,
M.W.; Garoutte, M. J. Chem. Educ., 2012, 89(5), 646-648. doi:10.1021/ed200015v
- “5-Bromomethyl-4,5-dihydroisoxazoles”, Mosher, M.D.; Norman, A.L.; Shurrush, K.A.
Tetrahedron Lett., 2009, 50, 5647-5648. doi:10.1016/j.tetlet.2009.07.106
- “Bis-anthracenyl Isoxazolyl Amides have Enhanced Anticancer Activity”, Gajewski, M.;
Beall, H.; Schnieder, M.; Stranahan, S.M.; Mosher, M.D.; Rider, K.C.; Natale, N.R.
Bioorg. Med. Chem. Lett., 2009, 19, 4067-4069; doi:10.1016/j.bmcl.2009.06.019
- “Design, Synthesis and Biological Evaluation of a Novel Class of Anticancer Agents:
Anthracenylisoxazole Lexitropsin Conjugates”, Han, X.; Li, C.; Mosher, M.D.; Rider,
K.C.; Zhou, P.; Crawford, R.L.; Fusco, W.; Paszczynski, A.; Natale, N.R. J. Bioorg. Med. Chem., 2009, 17, 1671-1680; doi:10.1016/j.bmc.2008.12.056