Lipase‐Mediated Conversion of Protecting Group Silyl Ethers: An Unspecific Side Reaction

Author:

Pick Lisa M.1,Wenzlaff Jessica1,Yousefi Mohammad2,Davari Mehdi D.2,Ansorge‐Schumacher Marion B.1ORCID

Affiliation:

1. Professur für Molekulare Biotechnologie Technische Universität Dresden 01062 Dresden Germany

2. Department of Bioorganic Chemistry Leibniz Institute of Plant Biochemistry Weinberg 3 06120 Halle Germany

Abstract

AbstractSilyl ether protecting groups are important tools in organic synthesis, ensuring selective reactions of hydroxyl functional groups. Enantiospecific formation or cleavage could simultaneously enable the resolution of racemic mixtures and thus significantly increase the efficiency of complex synthetic pathways. Based on reports that lipases, which today are already particularly important tools in chemical synthesis, can catalyze the enantiospecific turnover of trimethylsilanol (TMS)‐protected alcohols, the goal of this study was to determine the conditions under which such a catalysis occurs. Through detailed experimental and mechanistic investigation, we demonstrated that although lipases mediate the turnover of TMS‐protected alcohols, this occurs independently of the known catalytic triad, as this is unable to stabilize a tetrahedral intermediate. The reaction is essentially non‐specific and therefore most likely completely independent of the active site. This rules out lipases as catalysts for the resolution of racemic mixtures of alcohols through protection or deprotection with silyl groups.

Funder

Deutsche Forschungsgemeinschaft

Publisher

Wiley

Subject

Organic Chemistry,Molecular Biology,Molecular Medicine,Biochemistry

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