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Issue 22, 2011
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Formate dehydrogenase - a biocatalyst with novel applications in organic chemistry

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Abstract

In the field of industrial biocatalysis, formate dehydrogenase (FDH) is well established, in particular for its broad application in cofactor regeneration. Further applications have been limited by the enzyme's narrow range of substrates. These restrictions have been overcome now by the finding, that the enzyme is capable of selectively cleaving formic acid esters to the respective alcohol. Five homologous alkyl formates and phenyl formate as an aromatic ester were converted quantitatively by FDH from Candida boidinii in a batch reaction within 3 to 5 h. The substrates were turned irreversibly into carbon dioxide and the respective alcohol through hydride abstraction from the formyl group with full conversion. The mechanism shows parallels to hydrolysis reactions of the AAC1-type. KM-values and reactions rates of the tested formic acid esters display a tendency to higher conversion rates with increasing chain length. FDH emerged to be a superior deformylation catalyst compared to hydrolases as well as classical catalysts, as was shown by the selective deformylation of 1-acetoxy-4-formoxy butane (92%) and 1,3-bis(3-formoxypropyl)tetramethyldisiloxane. In particular its capability to distinguish between formic acid esters and non-formic acid esters renders the method particularly suitable for protective group chemistry. Furthermore the completeness of deformylation allows for converting substrates highly incompatible with aqueous media like siloxanes within a few hours.

Graphical abstract: Formate dehydrogenase - a biocatalyst with novel applications in organic chemistry

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Article information


Submitted
01 Jul 2011
Accepted
05 Sep 2011
First published
11 Oct 2011

Org. Biomol. Chem., 2011,9, 7941-7950
Article type
Paper

Formate dehydrogenase - a biocatalyst with novel applications in organic chemistry

P. Fröhlich, K. Albert and M. Bertau, Org. Biomol. Chem., 2011, 9, 7941
DOI: 10.1039/C1OB06064C

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