Associate Professor – Organic & Bioorganic Chemistry
Research and/or Creative Works
Research in our group spans the sub disciplines of synthesis and bioorganic chemistry and capitalizes in the synergy between the two areas. Our projects span a range of projects from the synthesis of peptide mimics, to proteomic approaches to the identification of protein-protein interactions, to development of methodology for the synthesis of combinatorial libraries to development of new synthetic methods. The synergy between bioorganic chemistry and synthesis is a strength of our program. For example, our peptidomimetic approaches are well grounded in organic chemistry principles such as conformational analysis and synthesis while often peptidomimetic targets necessitate the need for new synthetic methods and incidental chemistry inspires new synthetic methods.
R. M. Aranha, A. M. Bowser, J. S. Madalengoitia, “Facile 1,3-diaza-Claisen Rearrangements of Tertiary Allylic Amines Bearing an Electron Deficient Alkene” Org. Lett. 2009, 11, 575-578.
S. Flemer, A. Wurthmann, A. Mamai, J. S. Madalengoitia, “Strategies for the Solid-Phase Diversification of Poly-L-Proline Type II Peptide Mimic Scaffolds and Peptide Scaffolds Through Guanidinylation” J. Org. Chem. 2008, 73, 7953.
N. Huang, T. Jiang, T. Wang, M. Soukri, R. Ganorkar, B. Deker, J.-M. Leger, J. Madalengoitia, M. E. Kuehne, “The Acyclic Dieneamine Indoloacrylate Addition Route to Catharanthine” Tetrahedron 2008, 64, 9850.
S. Flemer, J. S. Madalengoitia, “Synthetic Routes into N-Pmc-N', N"-Disubstituted Guanidine Systems via Guanylation of Amines with N-Pmc-N'-alkyl Substituted Thioureas: Scope and Limitations of the Reaction” Synthesis 2007, 13, 81.
R. Ganorkar, A. Natarajan, A. Mamai, J. S. Madalengoitia "Synthesis of Conformationally Constrained Lysine Analogs" J. Org Chem. 2006, 71, 5004.
R. Zhang, A. Natarajan, S. Flemer, A. Mamai, C. Nickl, W. Dostmann, and J. S. Madalengoitia "Poly-L-Proline Type II Peptide Mimics as Probes of the Active Site Occupancy Requirements of cGMP Dependent Protein Kinase" J. Peptide Res. 2005, 66, 151-9.
A. M. Bowser and J. S. Madalengoitia "Synthesis of Highly Substituted Ureas and Thioureas Through 1,3-Diaza-Claisen Rearrangements" Tetrahedron Lett. 2005, 46, 2869.
A. M. Bowser and J. S. Madalengoitia "A 1,3-Diaza-Claisen Rearrangement that Affords Guanidines" Org. Lett. 2004, 6, 3409.
Mamai, A.; Madalengoitia, J. S. "Solid-Phase Guanidinylation as a Diversification Strategy of Poly-L-Proline Type II Peptide Mimic Scaffolds," Org. Lett. 2001, 3, 561.
Madalengoitia, J. S. "A Novel Peptide Fold: A Repeating βII'-Turn Secondary Structure" J. Am. Chem. Soc. 2000, 122, 4986.
Zhang, R.; Brownewell, F. E.; Madalengoitia, J. S. "Pseudo A(1,3) Strain as a Key Conformational Control Element in the Design of Poly-L-Proline Type II Peptide Mimics" J. Am. Chem. Soc. 1998, 120, 3894.
Areas of Expertise and/or Research
organic chemistry, bioorganic chemistry, peptide mimetics
- Ph.D., University of Virginia, Charlottesville, VA 1993
- Postdoctoral fellowship, University of California at Irvine, 1993-95
- (802) 656-8247