Non-Oxidative Enzymatic (De)Carboxylation of (Hetero)Aromatics and Acrylic Acid Derivatives.

Autor: Payer SE; Institute of Chemistry University of Graz Heinrichstrasse 28 8010 Graz Austria., Faber K; Institute of Chemistry University of Graz Heinrichstrasse 28 8010 Graz Austria., Glueck SM; Institute of Chemistry University of Graz Heinrichstrasse 28 8010 Graz Austria.
Jazyk: angličtina
Zdroj: Advanced synthesis & catalysis [Adv Synth Catal] 2019 Jun 06; Vol. 361 (11), pp. 2402-2420. Date of Electronic Publication: 2019 May 17.
DOI: 10.1002/adsc.201900275
Abstrakt: The utilization of carbon dioxide as a C 1 -building block for the production of valuable chemicals has recently attracted much interest. Whereas chemical CO 2 fixation is dominated by C-O and C-N bond forming reactions, the development of novel concepts for the carboxylation of C-nucleophiles, which leads to the formation of carboxylic acids, is highly desired. Beside transition metal catalysis, biocatalysis has emerged as an attractive method for the highly regioselective (de)carboxylation of electron-rich (hetero)aromatics, which has been recently further expanded to include conjugated α,β-unsaturated (acrylic) acid derivatives. Depending on the type of substrate, different classes of enzymes have been explored for (i) the ortho -carboxylation of phenols catalyzed by metal-dependent ortho -benzoic acid decarboxylases and (ii) the side-chain carboxylation of para -hydroxystyrenes mediated by metal-independent phenolic acid decarboxylases. Just recently, the portfolio of bio-carboxylation reactions was complemented by (iii) the para -carboxylation of phenols and the decarboxylation of electron-rich heterocyclic and acrylic acid derivatives mediated by prenylated FMN-dependent decarboxylases, which is the main focus of this review. Bio(de)carboxylation processes proceed under physiological reaction conditions employing bicarbonate or (pressurized) CO 2 when running in the energetically uphill carboxylation direction. Aiming to facilitate the application of these enzymes in preparative-scale biotransformations, their catalytic mechanism and substrate scope are analyzed in this review.
Databáze: MEDLINE
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