Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Screening of Biocatalysts for Synthesis of The Wieland-Miescher Ketone

Version 1 : Received: 26 August 2020 / Approved: 27 August 2020 / Online: 27 August 2020 (08:37:44 CEST)

A peer-reviewed article of this Preprint also exists.

Patel, M.P.; Green, N.T.; Burch, J.K.; Kew, K.A.; Hughes, R.M. Screening of Biocatalysts for Synthesis of the Wieland–Miescher Ketone. Catalysts 2020, 10, 1063. Patel, M.P.; Green, N.T.; Burch, J.K.; Kew, K.A.; Hughes, R.M. Screening of Biocatalysts for Synthesis of the Wieland–Miescher Ketone. Catalysts 2020, 10, 1063.

Journal reference: Catalysts 2020, 10, 1063
DOI: 10.3390/catal10091063

Abstract

Lipases, a versatile class of biocatalysts, have been shown to function in non-aqueous media/organic solvents and to possess promiscuous catalytic activity for a wide range of organic transformations. In this study, we explore the biocatalytic properties of a library of commercially available lipases by screening them for catalysis of a one-pot synthesis of Wieland-Miescher Ketone, an important intermediate in the synthesis of biologically active compounds such as steroids and terpenoids, from methyl vinyl ketone and 2-methyl-1,3-cyclohexanedione. As a direct outgrowth of this screen, we have created an optimized procedure for Wieland-Miescher Ketone (WMK) synthesis using crude lipase preparations, characterizing both reaction yield and enantiomeric excess. We have also identified principal components of the crude lipase mixture through proteomics and present evidence for a non-lipolytic origin of the observed catalysis. Finally, using the optimized conditions developed in this study, we propose a general absorbance-based screening methodology for assessing biocatalytic potential of crude enzyme preparations for synthesis of WMK.

Subject Areas

lipase; biocatalysis; Wieland-Miescher ketone; biocatalyst screening; amylase; peptidase; enantiomeric excess; Robinson Annulation

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