Cyclic peptides increase metabolic stability and cell permeability relative to their linear counterparts, and thus many are used as pharmaceutical drugs. Conventional methods for assembling cyclic peptides are challenging due to the high entropic cost when cyclizing the linear precursors. To address this issue, we are exploring an efficient and green strategy that uses dehydro-amino acid residues as turn inducers. The cyclic dehydro-peptides can be derivatized in a variety of ways with asymmetric catalysis, including: selective functionalization of C-H bonds of amino acids, asymmetric hydrogenation of dehydro-amino acids, and conjugate addition of dehydro-residues. This poster will show our progress towards late-stage asymmetric functionalization of cyclic dehydro-peptides.

Late-stage functionalization of cyclic dehydro-peptides

246th National Meeting (2013)

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