Novel continuous carboxylation using pressurized carbon dioxide by immobilized decarboxylase

Matsuda, Tomoko; Marukado, Ryo; Koguchi, Shinichi; Nagasawa, Tôru; Mukouyama, Masaharu; Harada, Tadao; Nakamura, Kaoru

doi:10.1016/j.tetlet.2008.08.004

Cited by 19 publications

(18 citation statements)

References 27 publications

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“…Heteroaromatic substrates : The first example for a non‐oxidative, reversible decarboxylation of a heteroaromatic carboxylate is the conversion of pyrrole‐2‐carboxylic acid ( 73a ) to pyrrole ( 73b ) by pyrrole‐2‐carboxylate decarboxylase from Bacillus megaterium PYR2910 [Figure , (a)] . The synthetic utility of the reverse carboxylation of pyrrole was demonstrated using excess bicarbonate (80% conversion, 52% isolated yield), pressurized CO 2 in a flow‐setup (24±7 μmol/h space‐time yield), or supercritical CO 2 (59% conversion) . Since the activity depends on the presence of (small) organic acids, a mechanism including an external carboxylate acting as catalytic base was proposed [Figure , (b)].…”

Section: Biocatalytic (De)carboxylation Of (Hetero)aromatics and αβ‐mentioning

confidence: 99%

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

2019

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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.

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Section: Biocatalytic (De)carboxylation Of (Hetero)aromatics and αβ‐mentioning

confidence: 99%

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

2019

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“…[49] Thed ecarboxylase underwent its reverse reactionu nder ah igh pressure of CO 2 (984 psi)t oa ffordp yrrole-2-carboxylic acid (59), demonstrating ay ield improvement in the flow systemo f2 5t imes compared to the corresponding batch system. [49] Thed ecarboxylase underwent its reverse reactionu nder ah igh pressure of CO 2 (984 psi)t oa ffordp yrrole-2-carboxylic acid (59), demonstrating ay ield improvement in the flow systemo f2 5t imes compared to the corresponding batch system.…”

Section: Enzyme-catalyzed Carboxylationmentioning

confidence: 99%

“…In 2008, a continuous flow system for the carboxylation of pyrrole with scCO 2 catalyzed by an immobilized decarboxylase enzyme was reported by Matsuda and co‐workers (Scheme ) . The decarboxylase underwent its reverse reaction under a high pressure of CO 2 (984 psi) to afford pyrrole‐2‐carboxylic acid ( 59 ), demonstrating a yield improvement in the flow system of 25 times compared to the corresponding batch system.…”

Section: C−c Bond Formation With Co2mentioning

confidence: 99%

Using Carbon Dioxide as a Building Block in Continuous Flow Synthesis

2018

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Carbond ioxide (CO 2 )i san attractive building block for organic synthesis that is environmentally friendly.C ontinuous flow technologies have enabled C À Oa nd C À Cb ondf orming reactions with CO 2 that previously were either low-yielding or impossible in batch to affordv alue-added chemicals. This review describes recent advancesi nc ontinuous flow as an enabling strategyi nu tilizing CO 2 as aC 1 building block in chemical synthesis.

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“…5 This immobilization method was applied because it was suitable for the reaction in scCO 2 for a decarboxylase-catalyzed carboxylation. 6 Moreover, this immobilization method has the advantage of a low diffusion barrier inside the gel layer around the enzyme, and stable operation was achieved for L-asparagic acid synthesis. 5 …”

Section: Immobilization Of the Whole Cellmentioning

confidence: 99%

Asymmetric reduction of ketones by Geotrichum candidum: immobilization and application to reactions using supercritical carbon dioxide

Matsuda

Marukado

Mukouyama

et al. 2008

Tetrahedron: Asymmetry

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Novel continuous carboxylation using pressurized carbon dioxide by immobilized decarboxylase

Cited by 19 publications

References 27 publications

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

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

Using Carbon Dioxide as a Building Block in Continuous Flow Synthesis

Asymmetric reduction of ketones by Geotrichum candidum: immobilization and application to reactions using supercritical carbon dioxide

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