Stephanie E. Sen
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Associate Professor
Organic and Bioorganic Chemistry |
| B.A., Bryn Mawr College,
1984
Ph.D., State University of New York Stony Brook, 1989
Dround Foundation Fellow, Research Institute of Scripps
Clinic, 1989-90
NIH Postdoctoral Fellow, Research Institute of Scripps
Clinic, 1990
NIH Postdoctoral Fellow, Stanford University, 1990-91 |
| Phone: (317)274-6889 |
| Email: sen@chem.iupui.edu
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Research |
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Publications |
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Sen
Lab Homepage |
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Research
Our work currently relates to three areas: i) juvenile
hormone (JH) metabolism; ii) biomimetic polyene cyclizations; and
iii) the development of new enzyme mimics. While the specific goals
for each project varies, they all ultimately relate to better understanding
how enzymes catalyze chemical transformations. To do so, we utilize
a combination of organic, biochemical, and computational methods.
Development of Insect Juvenile Hormone Inhibitors
Insects control their growth, morphology, behavior, and sexuality
with a complicated array of hormones. We are interested in understanding,
at the molecular level, how the insect hormone, JH, is made and
then use this information, construct compounds that will selectively
inhibit its formation. Three specific enzymes related to JH production
are currently under investigation, including prenyltransferase,
farnesol dehydrogenase, and isopentenyl diphosphate isomerase. The
long range goals of this project is to provide new targets for insecticide
development.
Biomimetic Polyene Cyclizations
Bimimicry is the process whereby natural processes are duplicated
under artificial conditions. In this regard, we are actively pursuing
the development of new methods for steroid and related polycycle
production, that mimic naturally-occurring enzymes. Zeolites, or
molecular sieves, are both porous and acidic inorganic materials,
which we believe can function as surrogates of polyene cyclization
enzymes, such as oxidosqualene cyclase. Development of this type
of cyclization methodology could greatly expand the chemistÕs
synthetic repertoire by allowing the preparation of both naturally
occurring and unnatural compounds.
Antibody-Assisted Chemical Transformations
Antibodies, prepared from the immune systems of higher organisms,
are highly efficient receptors. While their overall structures are
quite similar, antibodies contain a binding region which has been
fine tuned for a specific antigen. This characteristic can be used
to prepare proteins that serve as either chiral templates for regio-
and/or enantioselective chemical reactions or as catalysts. The
latter "abzymes" have the potential of performing transformations,
which are thus far inaccessible using chemical or enzymatic methods.
We are currently utilizing antibody technology to develop novel
detoxifying agents.
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Publications
Sperry, A.E and Sen, S.E. Partial purification of a farnesyl
diphosphate synthase from whole-body Manduca sexta. Insect Biochem.
Mol. Biol., 2002, 32, 889-899.
Sperry, A.E and Sen, S.E. Farnesol oxidation in insects: evidence
that the biosynthesis of insect juvenile hormone is mediated by
a specific alcohol oxidase. Insect Biochem. Mol. Biol.,
2001, 31, 171-178.
Sen, S.E.; Sperry, A.E.; and Hannemann, D.E. "Farnesol
Oxidation in Insects. Evidence for the Invovlement of a Specific
Alcohol Oxidase in Juvenile Hormone Biosynthesis" Insect
Biochem. Mol. Biol.1999, submitted.
Gachotte, D.; Sen, S.E.; Eckstein, J.; Barbuch,
R.; Kreiger, M.; Ray, B.D.; and Bard, M. "Characterization
of the Saccaromyces cerevisiae ERG27 gene encoding the 3-keto
reductase invovled in C-4 sterol demethylation" Proc. Natl.
Acad. Sci., USA1999, 96,12655-12660.
Sen, S.E.; Smith, S.M.; and Sullivan K. "Organic
Transformations using Zeolite and Zeotype Materials" Tetratedron(Report)
1999, 55,12657-12698.
Crowell, D.N.; Sen, S.E.; and Randall, S.K. "Prenylcysteine
a-Carboxyl Methyltransferse in Suspension-Cultured Tobacco Cells"
Plant Physiol.1998, 118,115-123.
S.E. Sen, Y.-z. Zhang, S.M. Smith, and J.C. Huffman
"Tricyclization of an Epoxypolyene Utilizing Zeolites as
Next-Generation Biomimetic Cyclization Promoters: Evidence of
Surface and Pore Selectivity in the Cyclization Process"
J. Org. Chem.1998, 63,4459-4465.
S.E. Sen, S.L. Roach, S.M. Smith, and Y.-z. Zhang,
"Ferric Chloride, an Efficient Promoter of Cationic Polyene
Cyclizations" Tetrahedron Lett.1998, 39,3969-3972.
Q. Tang, and S.E. Sen "Carbomethoxypropionyl
Cyanide: A Regioselective C-Acylation Reagent for the Preparation
of b-Dicarbonyl Compounds" Tetrahedron Lett.1998, 39,2249-2252.
S.E. Sen, S.L. Roach, G.J. Ewing,, J. Boggs, and
J. Magrath "Ferric Chloride Hexahydrate: A Mild Hydrolytic
Agent for the Deprotection of Acetals" J. Org. Chem.1997,
62,6684-6686.
S.E. Sen, and G.J. Ewing "Natural and Unnatural
Precursors of Insect Juvenile Hormone" J. Org. Chem.1997,
62,3529-3536.
Y.D. Burke, M.J. Stark, S.L. Roach, S.E. Sen, and
P.L. Crowell "Inhibition of Pancreatic Cancer Growth by the
Dietary Isoprenoids Farnesol and Geraniol" Lipids 1997, 32,151-156.
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