Madison Mikhail

Photo: 
First Name: 
Madison
Last Name: 
Mikhail
Official Title: 
Visa Coordinator
Contact Information
Office Location: 
450 N
Email: 
madmik@sas.upenn.edu
Phone: 
215-573-1246

Alice Chen

Photo: 
First Name: 
Alice
Last Name: 
Chen
Official Title: 
Administrative Assistant
Contact Information
Office Location: 
Room 3004 Vagelos Labs
Email: 
Alice2@sas.upenn.edu
Phone: 
215-573-5586

Yvonne Kline

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First Name: 
Yvonne
Last Name: 
Kline
Official Title: 
Administrative Assistant
Contact Information
Office Location: 
Room 124, 1973 Building
Email: 
ykline@sas.upenn.edu
Phone: 
215-898-7079

Bruno Fiorenza

Photo: 
First Name: 
Bruno
Last Name: 
Fiorenza
Official Title: 
Manager of Finance and Administration
Contact Information
Office Location: 
Room 133, 1973 Building
Email: 
fiorenza@sas.upenn.edu
Phone: 
215-898-8306

Leslie Shinn

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First Name: 
Leslie
Last Name: 
Shinn
Official Title: 
Coordinator, Undergraduate Biochemistry Program
Additional Titles: 
Coordinator, Vagelos Life Sciences Program
Contact Information
Office Location: 
Room 351, 1973 Wing
Email: 
lshinn@sas.upenn.edu
Phone: 
215-898-4771

Kristen Muscat

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First Name: 
Kristen
Last Name: 
Muscat
Official Title: 
Graduate Coordinator
Other Information: 
chemgrad@sas.upenn.edu (use for General Program/Admissions Inquiries and Graduate Course Permits)
Contact Information
Office Location: 
Room 130, 1973 Wing
Email: 
kmuscat@sas.upenn.edu
Phone: 
215-898-8334

Christopher Jeffrey

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First Name: 
Christopher
Last Name: 
Jeffrey
Official Title: 
Associate Director
Contact Information
Office Location: 
Room 127, 1973 Wing
Email: 
cjeffrey@sas.upenn.edu
Phone: 
215-898-9722

Robert Wertz

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First Name: 
Robert
Last Name: 
Wertz
Official Title: 
Grants Administrative Coordinator
Additional Titles: 
Webmaster
Contact Information
Office Location: 
454 N
Office Hours: 
m-f 9-5
Email: 
rwertz@sas.upenn.edu
Phone: 
215-573-7887

Jeffrey D. Winkler

Photo: 
First Name: 
Jeffrey D.
Last Name: 
Winkler
Official Title: 
Merriam Professor of Chemistry

Organic Chemistry 

Contact Information
Office Location: 
449 Chemistry Bldg.
Email: 
winkler@sas.upenn.edu
Phone: 
(215) 898-0052
Fax: 
(215) 573- 6329
Admin Support: 
Education: 
  • A.B. Harvard College (1977)
  • M.A., M.Phil., Ph.D. Columbia University (1981-83)
Research Interests: 

New Synthetic Pathways Based on the Intramolecular Dioxenone and Vinylogous Amide Photocycloaddition Reactions

We have developed these methods and have applied them to the first total syntheses of several molecules of biological importance, including manzamine A, 1, saudin, 2 , and ingenol, 3.

 

Total Synthesis of Manzamine-Related Structures

Current efforts in our laboratory are focused toward the synthesis of nakadomarin, 4, a structurally complex hexacyclic alkaloid that displays a range of promising biological activities including cytotoxic activity against murine lymphoma L1210 cells, inhibitory activity against cyclin dependent kinase 4, and anti-microbial activity against a fungus and a Gram-positive bacterium. We have also demonstrated that manipulation of the structure of 1 via Grubbs metathesis leads to the formation of novel structures, i.e., 5, with antibacterial properties comparable to those of ciprofloxacin. Finally, we have embarked on a program directed toward the synthesis of neokauluamine, 6, a dimeric manzamine with highly potent immunosuppressive properties. 

 

Transformations Using Organic Photochemistry

We have recently discovered a novel approach to the synthesis of substituted thiophenes 8 from arylsulfide enone precursors 7. The study of the mechanism of this unusual transformation (9 is a byproduct) as well as its application to the synthesis of more complex structures is currently underway in our laboratory.

 

Development of Novel Inhibitors of Hedgehog Signaling Based on Cyclopamine

Aberrant activation of the Sonic Hedgehog (Hh) signaling pathway has been associated with numerous malignancies in the brain, breast, pancreas and other organs. In vivo evidence suggests the antagonism of excessive Hh signaling may provide a route to unique mechanism-based therapies for the treatment of cancer. The steroidal alkaloid cyclopamine 10 suppresses the Hh signaling pathway, and has recently been been shown to be effective in the treatment of cancer using a variety of mouse models. Human cells are also sensitive, supporting the promising use of this natural product. However, the metabolic instability of cyclopamine precludes its clinical use. A significant demand exists for more stable cyclopamine-like structures. This project is directed toward the synthesis of cyclopamine-like structures, i.e., 11, from readily available metabolically-stable steroidal precursors, i.e., estrone.

 

Total Synthesis of Cortistatin A

The development of specific anti-angiogenic agents that could serve as anticancer chemotherapeutic agents is an important goal. In 2006, Kobayashi isolated the cortistatins from the marine sponge Corticium simplex. Cortistatin A 12 is the most active member of this family. It exhibits antiproliferative activity against human umbilical vein endothelial cells at nM concentrations. The total synthesis of the cortistatins and designed materials with cortistatin-like properties is one of the goals of our laboratory.

Bradford B. Wayland

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First Name: 
Bradford B.
Last Name: 
Wayland
Official Title: 
Emeritus Professor of Chemistry

Inorganic Chemistry

Contact Information
Office Location: 
Senior Faculty Suite
Email: 
wayland@sas.upenn.edu
Research Interests: 

Metallo-radical and organo-metal substrate reactions are used in both obtaining living radical polymerization for application in block copoymer materials and energy relevant small molecule organometallic transformations.

Our NSF supported polymer program spans areas from transition metal catalyst development and block co-polymer synthesis to materials applications of nano-structured polymer arrays in membranes, sensors, and microelectronic devices. The reactivity of metal-centered radical species and organometallic derivatives are exploited in the control of radical polymerization by catalytic chain transfer and living radical polymerization. Organo-cobalt porphyrin complexes have recently been observed to mediate a highly precise living radical polymerization of acrylate monomers to form low polydispersity homopolymers and block co-polymers. This new approach to obtaining living radical polymerization occurs by a degenerative transfer pathway that involves rapid interchange of polymeric radicals in the polymer with polymeric units in the organo-cobalt porphyrin complexes. This pathway to obtain living radical polymerization is a transition metal form of degenerative transfer that we refer to as radical interchange polymerization (RIP). The expanding capabilities of living radical polymerization to provide new classes of materials required to advance issues that have significant technological relevance are exploited through an active collaboration with materials science and engineering .Two of the issues targeted as focal points for this collaboration are 1) membranes for water purification and 2) low dielectric thin films for advanced micro electric devices. New materials design strategies are determined for each of the central topics along with the requisite approaches for polymer synthesis, morphology, and property evaluation.

The DOE supported energy related research interests are centered on developing new strategies to accomplish thermodynamically and or kinetically challenging reactions such as methane activation and carbon monoxide reductive coupling and hydrogenation. Ligands are designed to achieve high selectivity through steric and electronic constraints on forming the transition states for substrate reactions .The primary focus is on group nine (Co, Rh, Ir) metal complexes where the importance of metallo-radicals is a recurring theme. Metallo-porphyrins, chlorophylls, and related macrocycles are prominent thermal and photocatalysts in biological systems and emerging as important catalyst materials for chemical manufacturing processes. The unique unique chemical and physical properties of metallo-porphyrins and macrocyclic complexes are used in producing thermal and photocatalytic cycles for small molecule reactions. Several important examples include hydrogenation of CO and CO2, activation of methane, oxidation of alkenes, photoreductions and alkene polymerization. Tethered diporphyrin ligands have been designed and synthesized that are used in forming bimetalloradical complexes of Rh(II). Bimetalloradicals provide preorganization of transition states that involve two metalloradicals and give rapid highly selective substrate reactions. Structural, kinetic-mechanistic, thermodynamic, and reactivity studies are used in characterizing intermediates, anticipating new types of reactions, and guiding strategies to produce selective catalyst materials.

Other Affiliations: 

Temple University, Department of Chemistry

Department of Chemistry

231 S. 34 Street, Philadelphia, PA 19104-6323

215.898.8317 voice | 215.573.2112 fax | web@chem.upenn.edu

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