Biocatalytic Silylation: The Condensation of Phenols and Alcohols with Triethylsilanol

Sparkes, Emily I.; Egedeuzu, Chisom S.; Lias, Billie; Sung, Rehana; Caslin, Stephanie A.; Tabatabaei Dakhili, S. Yasin; Taylor, Peter G.; Quayle, Peter and Wong, Lu Shin (2021). Biocatalytic Silylation: The Condensation of Phenols and Alcohols with Triethylsilanol. Catalysts, 11(8) e879.

DOI: https://doi.org/10.3390/catal11080879

Abstract

Silicatein-α (Silα), a hydrolytic enzyme derived from siliceous marine sponges, is one of the few enzymes in nature capable of catalysing the metathesis of silicon–oxygen bonds. It is therefore of interest as a possible biocatalyst for the synthesis of organosiloxanes. To further investigate the substrate scope of this enzyme, a series of condensation reactions with a variety of phenols and aliphatic alcohols were carried out. In general, it was observed that Silα demonstrated a preference for phenols, though the conversions were relatively modest in most cases. In the two pairs of chiral alcohols that were investigated, it was found that the enzyme displayed a preference for the silylation of the S-enantiomers. Additionally, the enzyme’s tolerance to a range of solvents was tested. Silα had the highest level of substrate conversion in the nonpolar solvents n-octane and toluene, although the inclusion of up to 20% of 1,4-dioxane was tolerated. These results suggest that Silα is a potential candidate for directed evolution toward future application as a robust and selective biocatalyst for organosiloxane chemistry.

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