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Issue 53, 2017, Issue in Progress
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Chemoenzymatic one-pot reaction of noncompatible catalysts: combining enzymatic ester hydrolysis with Cu(I)/bipyridine catalyzed oxidation in aqueous medium

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Abstract

The combination of chemical catalysts and biocatalysts in a one-pot reaction has attracted considerable interest in the past years. However, since each catalyst requires very different reaction conditions, chemoenzymatic one-pot reactions in aqueous media remain challenging and are limited today to metal-catalysts that display high activity in aqueous media. Here, we report the first combination of two incompatible catalytic systems, a lipase based ester hydrolysis with a water-sensitive Cu/bipyridine catalyzed oxidation reaction, in a one-pot reaction in aqueous medium (PBS buffer). Key to the solution was the compartmentalization of the Cu/bipyridine catalyst in a core–shell like nanoparticle. We show the synthesis and characterization of the Cu/bipyridine functionalized nanoparticles and the application in the oxidation of allylic and benzylic alcohols in aqueous media. Furthermore, the work demonstrates the implementation of a one-pot reaction process with optimized reaction conditions involving a lipase (CAL-B) to hydrolyze various acetate ester substrates in the first step, followed by oxidation of the resulting alcohols to the corresponding aldehydes under aerobic conditions in aqueous media.

Graphical abstract: Chemoenzymatic one-pot reaction of noncompatible catalysts: combining enzymatic ester hydrolysis with Cu(i)/bipyridine catalyzed oxidation in aqueous medium

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Publication details

The article was received on 14 May 2017, accepted on 23 Jun 2017 and first published on 03 Jul 2017


Article type: Paper
DOI: 10.1039/C7RA05451C
RSC Adv., 2017,7, 33614-33626
  • Open access: Creative Commons BY license
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    Chemoenzymatic one-pot reaction of noncompatible catalysts: combining enzymatic ester hydrolysis with Cu(I)/bipyridine catalyzed oxidation in aqueous medium

    H. Sand and R. Weberskirch, RSC Adv., 2017, 7, 33614
    DOI: 10.1039/C7RA05451C

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