Event Information
Peter Wipf
(University of Pittsburgh)
Synthesis and Biological Evaluation of Peptide Mimetics
Departmental Seminar
Synthesis and Biological Evaluation of Peptide Mimetics
- Abstract:
- Peptide mimetics, in particular peptide bond isosteres, have had a long and mixed history in the pharmaceutical industry. In particular, the lack of an obvious design analogy between natural bioactive peptide sequences and similarly bioactive peptide mimetics has frustrated medicinal chemists. In this presentation, I will provide evidence that (1) appropriate substitutions at the sp2-carbon of alkene peptide isosteres are important to provide a good match of conformational and electronic properties of the parent peptide bond, (2) cascade hydrozirconation - Zr/Zn transmetalation - imine addition is a versatile methodology for (E)-alkene isostere synthesis
and the preparation of chemical libraries, and (3) organometallic multi-component C,C-bond formations can provide large increases in structural diversity and allow the rapid assembly of complex products from simple starting materials.
Hosts: David Beratan, Michael Goldsmith
Departmental Seminar