Cross‐metathesis of C‐Glycosides and Peptides

Abstract

Peptides bearing an acryloyl residue at their N‐terminus were coupled with various C‐glycosides in an equimolar ratio via cross‐metathesis. The newly formed olefin was obtained with high E/Z selectivity in satisfying to high yields with low homodimerization of the starting materials. The posttranslational cross‐metathesis approach was shown to be suitable for the combinatorial synthesis of a small library of C‐glycopeptides.

Keywords:

• C‐glycopeptides
• cross‐metathesis
• posttranslational synthesis

Acknowledgment

U.V. thanks Oliver von Ahsen for conducting biological assays on some of the glycopeptides.