Synthesis of backbone modified cyclic peptides bearing dipicolylamino sidearms

Three analogues of the Lissoclinum class of cyclic peptides, bearing dipicolylamino functionalised side chains, have been synthesised using a stepwise approach followed by macrocyclisation. Attempts to incorporate dipicolylamino functionalised side chains prior to peptide synthesis resulted in epimerisation, but this was overcome by functionalising the ornithine side chains with dipicolylamino groups after the macrocyclisation reaction.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide