New Foldamer Building Blocks

Foldamers are oligomers which have a tendency to form well-defined secondary structures.  We are exploring new foldamer backbones that contain g-amino acid residues. Current efforts in our group include:

1) We have developed efficient synthetic routes to new conformationally constrained g-peptide
building blocks. These efforts focused Michael additions1,2 that provide g-nitro acids, via asymmetric catalysis.

 

 

2) Cyclically-constrained g-amino acids provide conformational stability. Our group has shown that a/g-and b/g peptides promote helical conformation: 12-helix (1:1, ag), 13-helix (1:1, bg). Foldamer conformations are characterized by NMR (solution state) and X-ray crystallography (solid state).2

 

 

 

 

1. Chi, Y.; Guo, L.; Kopf, N. A. Gellman, S. H. J. Am. Chem. Soc. 2008, 130, 5608

2. Guo, L.; Chi, Y.; Almeida, A. M.; Guzei, I. A.; Parker, B. K.; Gellman, S. H. J. Am. Chem. Soc. 2009, 131, 16018