Biotinylated Metathesis Catalysts: Synthesis and Performance in Ring Closing Metathesis
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Nine biotinylated Grubbs–Hoveyda and Grubbs-type metathesis catalysts were synthesized and evaluated in ring closing metathesis reactions of N-tosyl diallylamine and 5-hydroxy-2-vinylphenyl acrylate. Their catalytic activity in organic- and aqueous solvents was compared with the second generation Grubbs–Hoveyda catalyst. The position of the biotin-moiety on the N-heterocyclic carbene was found to critically influence the catalytic activity of the corresponding ruthenium-based catalysts.
KeywordsFluorescence assay Aqueous catalysis Ring closing metathesis Coumarin Hoveyda–Grubbs
The authors thank The Seventh Framework Programme Project METACODE (KBBE, “Code-engineered new-to-nature microbial cell factories for novel and safety enhanced bio-production”) as well as ITN BioChemLig (FP7-ITN-238434) for financial support.