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Faculty
     
  Doug Frantz
Associate Professor

Office Phone: (210) 458-7048
Office: BSE 4.258
E-Mail: doug.frantz@utsa.edu

Areas of Specialization
• Medicinal Chemistry
• Process Chemistry
• Asymmetric Catalysis
• Heterocyclic Synthesis
• Physical Organic Chemistry


Laboratory Web Page
http://www.utsa.edu/chem/faculty/dougfrantz/index.html

 






Research Interests

The centralized theme of research in my lab involves the application and development of new synthetic methodology in organic chemistry that can provide new avenues of chemical reactivity while keeping practicality as a viable and equally important goal. Many of the reactions we develop are mediated by late-transition metals catalysts that are fine-tuned through the use of real-time quantitative techniques allowing us to rapidly screen new reactions and parameters with unparalleled efficiency in academia. Furthermore, my lab is also involved with several medicinal chemistry programs aimed at developing new small molecule probes towards studying the mechanisms of stem cell differentiation. Students in my lab learn techniques in synthetic chemistry, medicinal chemistry, analytical chemistry, physical organic chemistry and drug discovery and development.





Selected Publications

 

Crouch, I. T.; Neff, R. K.; Frantz, D. E. “Pd-Catalyzed Asymmetric Beta-Hydride Elimination En Route to Chiral Allenes” J. Am. Chem. Soc. 2013, ASAP.


Scheuermann, T. H.; Li, Q.; Ma, H. –W.; Key, J.; Zhang, L.; Chen, R.; Garcia, J. A.; Naidoo, J.; Longgood, J.; Frantz, D. E.; Tambar, U. K.; Gardner, K. H.; Bruick, R. K. “Allosteric Inhibition of Hypoxia Inducible Factor 2 with Small Molecules” Nature Chem. Bio. 2013, In Press.


Rogers, J. L. Bayeh, L.; Scheuermann, T. H.; Longgood, J.; Caldwell, C.; Key, J.; Naidoo, J.; Melito, L.; Shokri, C.; Frantz, D. E.; Bruick, R. K.; Gardner, K. H.; MacMillan, J. B.; Tambar, U. K. “Development of Inhibitors of the PAS-B Domain of the HIF-2a Transcription Factor” J. Med. Chem. 2013, In Press.


Babinksi, D. J.; Bao, X.; El Arba, M.; Chen, B.; Hrovat, D. A.; Borden, W. T.; Frantz, D. E. “Synchronized Aromaticity as an Enthalpic Driving Force for the Aromatic Cope Rearrangement” J. Am. Chem. Soc. 2012, 134, 16139.


Kato, M.; Han, T. W.; Xie, S.; Shi, K.; Du, X.; Wu, L. C.; Mirzaei, H.; Goldsmith, E. J.; Longgood, J.; Pei, J.; Grishin, N. V.; Frantz, D. E.; Schneider, J. W.; Chen, S.; Li, L.; Sawaya, M. R.; Eisenberg, D.; Tycko, R.; McKnight, S. L. “Cell-free formation of RNA granules: Low complexity sequence domains form dynamic fibers within hydrogels.” Cell, 2012, 149, 753-767.


Zang, Q. S.; Hesham, S.; Maass, D. L.; Martinez, B.; Ma, L.; Kilgore, J. A.; Williams, N. S.; Frantz, D. E.; Wigginton, J. G.; Nwariaku, F. E.; Wolf, S. E.; Minei, J. P. “Specific Inhibition of mitochondrial oxidative stress suppresses inflammation and improves cardiac function in a rat pneumonia-related sepsis model.” American Journal of Physiology-Heart and Circulatory Physiology, 2012, 302, H1847-H1859.


Russell, J. L.; Goetsch, S. C.; Aguilar, H. R.; Coe, H.; Luo, X.; Liu, N.; van Rooij, E.; Frantz, D. E.; Schneider, J. W. “Targeting Native Adult Heart Progenitors with Cardiogenic Small Molecules.” ACS Chemical Biology, 2012, 7, 1067.


Russell, J. L.; Goetsch, S. C.; Aguilar, H. R.; Frantz, D. E.; Schneider, J. W. “Regulated expression of pH sensing G protein-coupled receptor-68 identified through chemical biology defines a new drug target for ischemic heart disease.” ACS Chemical Biology, 2012 7, 1077.


Hartley, R. M.; Peng, J.; Fest, G. A.; Dakshanamurthy, S.; Frantz, D. E.; Brown, M. L.; Mooberry, S. L.  “Polygamain, a new microtubule depolymerizing agent that occupies a unique pharmacophore in the colchicine site.”  Mol. Pharm. 2012, 81, 431.


Mata, M. A.; Satterly, N.; Versteeg, G. A.; Frantz, D. E.; Wei, S.; Williams, N.; Schmolke, M.; Peña-Llopis, S.; Brugarolas, J.; Forst, C. V.; White, M. A.; Garcia-Sastre, A.; Roth, M. G.; Fontoura, B. M. A. “Chemical inhibition of RNA viruses reveals REDD1 as a host defense fact.” Nature Chem, Bio. 2011, 7, 712-719.


Babinski, D. J.; Aguilar, H. A.; Still, R.; Frantz, D. E. “Synthesis of substituted pyrazoles via tandem cross-coupling/electrocyclization of enol triflates and diazoacetates.”

J. Org. Chem. 2011, 5915. (Featured Article and Highlighted by SYNFACTS)


Crouch, I. T.; Dreier, T.; Frantz, D. E. “Palladium-catalyzed elimination/isomerization of enol triflates into 1,3-dienes.” Angew. Chem. Int. Ed. 2011, 6128-6132.

(Highlighted by SYNFACTS)


Wang, Y. X.; Zang, Q. S.; Liu, Z. J.; Wu, Q.; Maass, D.; Dulan, G.; Shaul, P. W.; Melito, L.; Frantz, D. E.; Kilgore, J. A.; Williams, N. S.; Terada, L. S.; Nwariaku, F. E. “Regulation of VEGF-induced endothelial cell migration by mitochondrial reactive oxygen species.” Am. J. Phys. Cell Phys. 2011, 301, C695-C704.


Zhang, L.; Peng, L.; Hsu, T.; Aguilar, H. R.; Frantz, D. E.; Schneider, J. W.; Bachoo, R. M.; Hsieh, J. “Small-molecule blocks malignant astrocyte proliferation and induces neuronal gene expression.” Differentiation 2011, 81, 233-242.


Peng, J.; Jackson, E. M.; Babinski, D. J.; Risinger, A. L.; Helms, G.; Frantz, D. E.; Mooberry, S. L. “Evelynin, a ctyotoxic benzoquinone-type retro-dihydrochalcone from Tacca chantrieri.” J. Nat. Prod. 2010, 73,1590

 

 

An Alternative Polyamine Biosynthetic Pathway Is Widespread in Bacteria and Essential for Biofilm Formation in Vibrio cholerae
Lee, J., Sperandio, V., Frantz, D. E., Longgood, J., Camilli, J., Phillips, M. A., Michael, A. J. J.
Biol. Chem. 2009, 284, 9899.

 


 

Process Development of a Potent Bradykinin 1 Antagonist
Menzel, K., Machrouhi, F., Bodenstein, M., Alorati, A., Cowden, C., Gibson, A. W., Bishop, B., Ikemoto, N., Nelson, T. D., Kress, M. H., Frantz, D. E.
"Org. Process Res. Dev. 2009, 13, 519.

 

 


Process Development of a Potent Bradykinin 1 Antagonist
Schneider, J. W.; Gao, Z.; Li, S.; Farooqi, M.; Tang, T., -S.; Bezprozvanny, I.; Frantz, D. E.; Hsieh, J.
Nature Chem. Bio 2008, 4, 408.

 

 

 

Stereoselective Synthesis of Acetoacetate-Derived Enol Triflates
Babinski, D.; Soltani, O.; Frantz, D. E.
Org. Lett. 2008, 10, 2901.

 

 

 

Cardiogenic small molecules that enhance myocardial repair by stem cells
Sadek, H.; Hannack, B.; Choe, E.; Wang, J.; Latif, S.; Garry, M. G.; Garry, D. J.; Longgood, J.; Frantz, D. E.; Olson, E. N.; Hsieh, J,; Schneider, J. W.
Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 6063-6068.

 

 

 

Substitution effect on the regioselective halogen/metal exchange of 3-substituted 1,2,5-tribromobenzenes
Menzel, K.; Mills, P. M.; Frantz, D. E.; Nelson, T. D.; Kress, M. H.
Tetrahedron Lett. 2008, 49, 415-418.

 

 

 

High-Throughput Screen for Small Molecule Inhibitors of Mint1-PDZ Domains
Chen, X.; Longgood, J. C.; Michnoff, C.; Wei, S.; Frantz, D. E.; Bezprozvanny, I.
Assay and Drug Development Technologies 2007, 5, 769-784.

 

 

 

Halogen - metal exchange of 3-substituted 1,2-dibromoarenes: the use of long-range JCH coupling constants to determine regiochemistry
DiMichele, L.; Menzel, K.; Mills, P.; Frantz, D. E..; Nelson, T. D.
Magn. Reson. Chem. 2006, 44, 1041-1043.

 

 

 

An Improved Method for the Bromination of Metalated Haloarenes via Lithium, Zinc Transmetalation: A Convenient Synthesis of 1,2-Dibromoarenes
Menzel, K.; Fisher, E. L.; DiMichele, L.; Frantz, D. E.; Nelson, T. D.; Kress, M. H.
J. Org. Chem. 2006, 71,2188-2191.

 

 

 

Regioselective Halogen-Metal Exchange Reaction of 3-Substituted 1,2-Dibromo Arenes: The Synthesis of 2-Substituted 5-Bromobenzoic Acids
Menzel, K.; DiMichele, L.; Mills, P.; Frantz, D. E.; Nelson, T. D.; Kress, M. H.
Synlett 2006, 12, 1948-1952.


 

 

 

 

Current graduate students

 

David Babinski
Current project involves the use of stereodefined enol triflates in catalytic Pd-mediated reactions

 

Hector Aguilar
Current project involves the developing new routes to novel heterocyclic small molecules that are capable of inducing stem cell differentiation

 

Ian Crouch
Current project involves the chromatography free synthesis of alkynoates and allenoates and the extension of new transition metal mediated processes.

 

 

 

 

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