In 2003, our group reported the synthesis of the first molecules classed as �bis-peptides�. Bis-peptides are spiro-oligmeric compounds composed of stereochemically pure monomers that possess two a-amino acids on a cyclic core. This synthesis was performed using common Fmoc-based solid phase peptide synthesis protocols followed by a rigidification step resulting in good purity and yield. In 2008, new methodology was introduced that allowed the introduction of internal functionality into bis-peptides, and in 2011, this method was adapted for solid phase synthesis using a Boc/tert-butyl based approach. This approach provides highly functionalized bis-peptides in good purity but isolated yields are consistently low. This poster describes improvements of the Boc/tert-butyl based method for the solid-phase synthesis of highly functionalized bis-peptides as well as the usefulness of the Fmoc-based approach toward multivalent displays.

Solid phase synthesis of bis-peptides: Then and now

244th National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.