Talk Session: SESSION 9: INNOVATIONS IN PEPTIDE AND PROTEIN CHEMISTRY
Date: Tuesday, June 14, 2022
Talk Time: 10:45 am - 11:10 am
Talk Title: New Methods for Construction of Complex Peptide Macrocycles
1998 BS, Nanjing University, China; 2004 Ph.D., Columbia University, USA
2015-present Professor, State Key Laboratory of Elemento-organic Chemistry, Nankai University, China; 2018-present Adjunct professor, The Pennsylvania State University, USA; 2014-2015 Associate Professor, Department of Chemistry, The Pennsylvania State University; 2008-2014 Assistant Professor, Department of Chemistry, The Pennsylvania State University, USA;2005-2008 Postdoctoral fellow, Memorial Sloan-Kettering Cancer Center, USA
Cyclic peptides have provided an important platform for exploration of biorelevant chemical space between small molecules and biologics. In comparison with the state of the art synthesis of small molecules, chemists' ability to fine-tune the three-dimensional structures and properties of cyclic peptides is much limited.
In this talk, I will discuss our recent investigation of various chemical strategies, including metal-catalyzed, radial-mediated and classical polar reactions, for synthesis of peptide macrocycles with different structure features:
1) Construction of cyclophane-braced peptide macrocycles via palladium-catalyzed intramolecular arylation of various C-H bonds
2) Streamlined construction of S-aryl ether linked peptide macrocycles via palladium-catalyzed intramolecular S-arylation in solution and on DNA template
3) Cooperative stapling of unprotected peptides at lysine and tyrosine or arginine with simple formaldehyde.