Working Paper Article Version 1 This version is not peer-reviewed

Biocatalytic Silylation: The Condensation of Phenols and Alcohols with Triethylsilanol

Version 1 : Received: 26 June 2021 / Approved: 28 June 2021 / Online: 28 June 2021 (13:43:42 CEST)

A peer-reviewed article of this Preprint also exists.

Sparkes, E.I.; Egedeuzu, C.S.; Lias, B.; Sung, R.; Caslin, S.A.; Tabatabaei Dakhili, S.Y.; Taylor, P.G.; Quayle, P.; Wong, L.S. Biocatalytic Silylation: The Condensation of Phenols and Alcohols with Triethylsilanol. Catalysts 2021, 11, 879. Sparkes, E.I.; Egedeuzu, C.S.; Lias, B.; Sung, R.; Caslin, S.A.; Tabatabaei Dakhili, S.Y.; Taylor, P.G.; Quayle, P.; Wong, L.S. Biocatalytic Silylation: The Condensation of Phenols and Alcohols with Triethylsilanol. Catalysts 2021, 11, 879.

Journal reference: Catalysts 2021, 11, 879
DOI: 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 non-polar 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 towards future application as a robust and selective bi-ocatalyst for organosiloxane chemistry.

Subject Areas

Silicatein; condensation; silyl ether; organosiloxane; biocatalysis

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