Weiming Wu

Education

B.S. (1986) Nanjing Univ., Chemistry
Ph.D. (1992) Univ. of Illinois, Chemistry

Research Areas: Bioorganic Chemistry and Enzymology

Our research group is interested in the investigation of enzymatic mechanisms through model systems and in the design, synthesis, and study of enzyme substrate analogs. These analogs are designed to elucidate the catalytic mechanism of biologically important enzymes. The possibility of these analogs being developed as medicinal agents will also be investigated. Current interests concern an enzyme in the nucleic acid biosynthetic pathway, orotidine-5'-monophosphate decarboxylase.

Patent

Ge, Y.; He, Z.; Wu, W. “Methods of Inhibiting Cyanobacteria by Administering Gramine Derivatives”, US Patent 8,945,397 B2.

Publications (last ten years)

Koehn, S. K.; Tran, N. L.; Gronert, S.; Wu, W.

“The Stability of Aryl Carbanions Derived from Pyridine N-Oxide: The Role of Resonance in Stabilizing Aryl Anions,” J. Am. Chem. Soc. 2010, 132, 390-395.

Wong, F. M.; Chan, Y. M.; Chen, D. X.; Wu, W.

“Convenient One-Pot Synthesis of trans-1,2-Diaryloxiranes from the Direct Coupling of Benzyl Halides”, Tetrahedron Lett. 2010, 51, 6649-6650.

Wang, C.; Wu, W.

“A Simple Method to Determine the R/S Configuration of Molecules with an Axis of Chirality”, J. Chem. Edu. 2011, 88, 299-301.

Huang, S.; Wong, F. M.; Gassner, G. T.; Wu, W.

“Hydrolysis of α-Halo and α-Cyano Pyridinium: Great Rate Enhancement by the Positive Charge and a Model for ODCase-Catalyzed Hydrolysis”, Tetrahedron Lett. 2011, 52, 3960-3962.

Huang, S.; Gronert, S.; Wu, W.

“Polarization in the Structures of Uracil and Thiouracils:  Implication for Binding with Orotidine 5’-Monophosphate Decarboxylase”, Bioorg. Med. Chem. Lett. 2011, 21, 6341-6342.

Tan, R. C.; Vien, J. Q. T.; Wu, W.

“Hydrolysis of α-Chloro-Substituted 2- and 4-Pyridones: Rate Enhancement by Zwitterionic Structure”, ”, Bioorg. Med. Chem. Lett. 2012, 22, 1224-1225.

Tsang, Y.-W.; Wood, B. M; Wong, F. M.; Wu, W.; Gerlt, J. A.; Amyes, T. L.; Richard, J. P.

“Proton Transfer from C‑6 of Uridine 5′-Monophosphate Catalyzed by Orotidine 5′-Monophosphate Decarboxylase: Formationand Stability of a Vinyl Carbanion Intermediate and the Effect of a 5‑Fluoro Substituent”, J. Am. Chem. Soc. 2012, 134, 14580-14594.

Senger, N. A.; Bo, B.; Cheng, Q.; Keeffe, J. R.; Gronert, S.; Wu, W.

“The Element Effect Revisited:  Factors Determining Leaving Group Ability in Activated Nucleophilic Aromatic Substitution Reactions”, J. Org. Chem. 2012, 77, 9535-9540.

Senger, N. A.; Bliss, C. E.; Keeffe, J. R.; Gronert, S.; Wu, W.

“Stabilities of uracil and pyridone-based carbanions: a systematic study in the gas phase and solution and implications for the mechanism of orotidine-5’-monophosphate decarboxylase”, Tetrahedron 2013, 69, 5287-5292.

Senger, N. A.; Bowler, J. T.; Mercado, R. S.; Lin, S.; Wu, W.

Improved synthesis of N1-substituted orotic acid derivatives, Tetrahedron Lett. 2013, 54, 4245-4246

Chen, Y.-P.; Catbagan, C. C.; Bowler, J. T.; Gokey, T.; Goodwin, N. D. M.; Guliaev, A. B.; Wu, W.; Amagata, T.

“Evaluation of Benzoic Acid Derivatives as Sirtuin Inhibitors”, Bioorg. Med. Chem. Lett. 2014, 24, 349-352..

Tan, C.; Yan, P.; Ye, W.; Yao, J.; Wu, W.; Wang, C.

“Iodine-Promoted Synthesis of 1-Alkyl-3-aroylindolizines from N-(Aroylmethyl)-pyridinium Salts and Aliphatic Aldehydes”, Heteroatom Chem. 2014, 25, 72-81.

Bowler, J. T.; Wong, F. M.; Gronert, S.; Keeffe, J. R.; Wu, W.

“Reactivity in the Nucleophilic Aromatic Substitution Reactions of Pyridinium Ions”, Org. Biomol. Chem. 2014, 12, 6175-6180.

Bowler, J. T.; Clausen, C. R.; Blackburn, D. J.; Wu, W.

“Convenient Synthesis of N1-Substituted Orotic Acid Derivatives”, Tetrahedron Lett. 2014, 55, 6465-6466.

McGraw, K. M.; Bowler, J. T.; Ly, V. T.; Erden, I.; Wu, W.

“Reductive debromination of 1,2-dibromides with anisidines”, Tetrahedron Lett. 2016, 57, 285-287.

Kent, G. T.; Blackburn, D. J.; Gonzalez, J. R.; Mayer, M. L.; Wu, W.

“Convenient synthesis of phosphonohydrazines from arylamines”, Tetrahedron Lett. 2016, 57, 2097-2099.

Thompson, C. M.; Orellana, M. D.; Lloyd, S. E.; Wu, W.
“Stereospecific synthesis of cis-stilbenes from benzaldehydes and phenylacetic acids via sequential Perkin condensation and decarboxylation”, Tetrahedron Lett. 2016, 57, 4866-4868.

Blackburn, D. J.; Kent, G. T.; Wu, W 

“Regiospecific synthesis of 6-halouridine derivatives:  an effective method for coupling sterically hindered pyrimidine bases to ribose”, Tetrahedron Lett. 2017, 58, 1348-1350.

McGraw, K. M.; Kent, G. T.; Gonzalez, J. R.; Erden, I.; Wu, W 

“Competitive, substrate-dependent reductive debromination/dehydrobromination of 1,2-dibromides with triethylamine”, Tetrahedron Lett. 2017, 58, 1973-1975.

Tang, K. G.; Kent, G. T.; Erden, I.; Wu,

“cis-β-Bromostyrene derivatives from cinnamic acids via a tandem substitutive bromination-decarboxylation sequence”, Tetrahedron Lett. 2017, 58, 3894-3896.

Orellana, M. D.; Knapp, M. R.; Zhang, Z.; Lloyd, S. E.; Wu, W

“Convenient synthesis of N-substituted b-lactam-4-carboxylates”, Tetrahedron Lett. 2018, 59, 2434-2435.

Czub, M. P.; Zhang, B.#; Chiarelli, M. P.; Majorek, K. A.; Joe, L.#; Porebski, P. J.; Revilla, A.; Wu, W.; Becker, D. P.; Minor, W.; Kuhn, M. L.

“A Gcn5-related N-acetyltransferase (GNAT) that selectively acetylates