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Expanding the Scope of Biocatalysis: Oxidative Biotransformations on Solid-Supported Substrates.

Authors
  • Brooks, Sarah J1
  • Coulombel, Lydie
  • Ahuja, Disha
  • Clark, Douglas S
  • Dordick, Jonathan S
  • 1 Department of Chemical and Biological Engineering, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Nanotechnology Center, Rensselaer Polytechnic Institute, Troy, NY, 12180, USA.
Type
Published Article
Journal
Advanced Synthesis & Catalysis
Publisher
Wiley
Publication Date
Jul 07, 2008
Volume
350
Issue
10
Pages
1517–1525
Identifiers
PMID: 21881621
Source
Medline
Language
English
License
Unknown

Abstract

Oxidative biocatalytic reactions were performed on solid-supported substrates, thus expanding the repertoire of biotransformations that can be carried out on the solid phase. Various phenylacetic and benzoic acid analogs were attached to controlled pore glass beads via an enzyme-cleavable linker. Reactions catalyzed by peroxidases (soybean and chloro), tyrosinase, and alcohol oxidase/dehydrogenase gave a range of products, including oligophenols, halogenated aromatics, catechols, and aryl aldehydes. The resulting products were recovered following cleavage from the beads using α-chymotrypsin to selectively hydrolyze a chemically non-labile amide linkage. Controlled pore glass (CPG) modified with a polyethylene glycol (PEG) linker afforded substantially higher product yields than non-PEGylated CPG or non-swellable polymeric resins. This work represents the first attempt to combine solid-phase oxidative biotransformations with subsequent protease-catalyzed cleavage, and serves to further expand the use of biocatalysis in synthetic and medicinal chemistry.

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