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Article

Biocatalytic Silylation: The Condensation of Phenols and Alcohols with Triethylsilanol

1
Manchester Institute of Biotechnology, University of Manchester, 131 Princess Street, Manchester M1 7DN, UK
2
Department of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK
3
Faculty of Science, Technology, Engineering and Mathematics, Open University, Walton Hall, Milton Keynes MK7 6AA, UK
*
Author to whom correspondence should be addressed.
Academic Editors: Evangelos Topakas, Roland Wohlgemuth and David D. Boehr
Catalysts 2021, 11(8), 879; https://doi.org/10.3390/catal11080879
Received: 26 June 2021 / Revised: 16 July 2021 / Accepted: 20 July 2021 / Published: 22 July 2021
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. View Full-Text
Keywords: silicatein; condensation; silyl ether; organosiloxanes; biocatalysis silicatein; condensation; silyl ether; organosiloxanes; biocatalysis
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MDPI and ACS Style

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

AMA Style

Sparkes EI, Egedeuzu CS, Lias B, Sung R, Caslin SA, Tabatabaei Dakhili SY, Taylor PG, Quayle P, Wong LS. Biocatalytic Silylation: The Condensation of Phenols and Alcohols with Triethylsilanol. Catalysts. 2021; 11(8):879. https://doi.org/10.3390/catal11080879

Chicago/Turabian Style

Sparkes, Emily I., Chisom S. Egedeuzu, Billie Lias, Rehana Sung, Stephanie A. Caslin, S. Y. Tabatabaei Dakhili, Peter G. Taylor, Peter Quayle, and Lu S. Wong 2021. "Biocatalytic Silylation: The Condensation of Phenols and Alcohols with Triethylsilanol" Catalysts 11, no. 8: 879. https://doi.org/10.3390/catal11080879

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