Abstract
Hoveyda–Grubbs-type complexes, ruthenium catalysts for olefin metathesis, have gained increased interest as a research target in the interdisciplinary research fields of chemistry and biology because of their high functional group selectivity in olefin metathesis reactions and stabilities in aqueous media. This review article introduces the application of designed Hoveyda–Grubbs-type complexes for bio-relevant studies including the construction of hybrid olefin metathesis biocatalysts and the development of in-vivo olefin metathesis reactions. As a noticeable issue in the employment of Hoveyda–Grubbs-type complexes in aqueous media, the influence of water on the catalytic activities of the complexes and strategies to overcome the problems resulting from the water effects are also discussed. In connection to the structural effects of protein structures on the reactivities of Hoveyda–Grubbs-type complexes included in the protein, the regulation of metathesis activities through second-coordination sphere effect is presented, demonstrating that the reactivities of Hoveyda–Grubbs-type complexes are controllable by the structural modification of the complexes at outer-sphere parts. Finally, as a new-type reaction based on the ruthenium-olefin specific interaction, a recent finding on the ruthenium complex transfer reaction between Hoveyda–Grubbs-type complexes and biomolecules is introduced.
Highlights
Transition metal-catalyzed olefin metathesis (OM), the rearrangement of C–C double bonds, has gained its importance in organic synthesis because a variety of OM reaction fashions are applicable for the syntheses of natural products and bioactive compounds [1,2,3]
Artificial metalloenzyme), synthetically conartificial metalloenzymes (ArMs; ArM = artificial metalloenzyme), synthetically constructed structed enzymes with a metal complex embedded in protein scaffolds, have the potential structed enzymes with a metal complex embedded in protein scaffolds, have the potential enzymes with a metal complex embedded in protein scaffolds, have the potential to to mediate abiological typeswith ofwith reaction, with design of metalinserted complexes inserted into to mediate abiological types reaction, design of metal complexes inserted mediate abiological types of of reaction, thethe design ofthe metal complexes intointo the theIn protein core
The circular dichroism (CD) signals were observed for the complex in α-CT, whereas no CD signal appeared without α-CT
Summary
Transition metal-catalyzed olefin metathesis (OM), the rearrangement of C–C double bonds, has gained its importance in organic synthesis because a variety of OM reaction fashions (shown in Scheme 1) are applicable for the syntheses of natural products and bioactive compounds [1,2,3]. Among transition metal catalysts used for OM reactions, a series of Grubbs catalyst and its derivatives (1–5; shown in Figure 1), catalysts with a ruthenium center, are the most popular catalysts both in industrial and laboratory-scale reactions [4]. This is because these catalysts are properly stable under the air compared to other transition metal complexes for OM reactions, such as Schrock-type complexes with a molybdenum center.
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