Light‐Driven Enzymatic Decarboxylation of Fatty Acids

Huijbers, Mieke M.E.; Zhang, Wuyuan; Tonin, Fabio; Hollmann, Frank

doi:10.1002/anie.201807119

Cited by 159 publications

(193 citation statements)

References 22 publications

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“…To the best of our knowledge,n oe xamples of enantioselective reactions catalyzed by CvFAPhave been reported to date. [10,11] Herein, we demonstrate an ew KR method catalyzed by engineered CvFAPv ariants for the synthesis of chiral a-hydroxy/amino carboxylic acids.T his photo-activated biotransformation proceeds without NADPH circulation or any other reaction pretreatment, thus providing am ore efficient route to chiral compounds with high activity and stereoselectivity (Scheme 1).…”

mentioning

confidence: 99%

Light‐Driven Kinetic Resolution of α‐Functionalized Carboxylic Acids Enabled by an Engineered Fatty Acid Photodecarboxylase

Fan

et al. 2019

Angew Chem Int Ed

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Chiral a-functionalized carboxylic acids are valuable precursors for avariety of medicines and natural products. Herein, we described an engineered fatty acid photodecarboxylase (CvFAP)-catalyzed kinetic resolution of a-amino acids and a-hydroxy acids,w hich provides the unreacted R-configured substrates with high yields and excellent stereoselectivity (ee up to 99 %). This efficient light-driven process requires neither NADPH recycling nor prior preparation of esters, which were required in previous biocatalytic approaches.T he structure-guided engineering strategy is based on the scanning of large amino acids at hotspots to narrowthe substrate binding tunnel. To the best of our knowledge,this is the first example of asymmetric catalysis by an engineered CvFAP.

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confidence: 99%

Light‐Driven Kinetic Resolution of α‐Functionalized Carboxylic Acids Enabled by an Engineered Fatty Acid Photodecarboxylase

Fan

et al. 2019

Angew Chem Int Ed

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“…to the hydrogen donor. Hollmann and co‐workers utilized a short‐length construct of Cv FAP as a crude enzyme preparation for decarboxylation to afford hydrocarbons 114 (Table ) . The lysate proved to be more active and robust than the purified enzyme under the reaction conditions used.…”

Section: Application Of Photoenzymes and Enzymes With Altered Activitymentioning

confidence: 99%

“…Hydrolysis combined with fatty acid photodecarboxylation in a bi-enzymatic cascade reaction. [100] Table 6. Light-promoted reactionsc atalyzedb yf atty acid photodecarboxylase (CvFAP).…”

Section: Photoenzymes and Generation Of Altered Activity By Irradiationmentioning

confidence: 99%

Biocatalysis Fueled by Light: On the Versatile Combination of Photocatalysis and Enzymes

Seel

Gulder

2019

ChemBioChem

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Enzymes catalyze a plethora of highly specific transformations under mild and environmentally benign reaction conditions. Their fascinating performances attest to high synthetic potential that is often hampered by operational obstacles such as in vitro cofactor supply and regeneration. Exploiting light and combining it with biocatalysis not only helps in overcoming these drawbacks, but the fruitful liaison of these two fields of “green chemistry” also offers opportunities to unlock new synthetic reactivities. In this review we provide an overview of the wide variety of photo‐biocatalysis, ranging from the photochemical delivery of electrons required in redox biocatalysis and photochemical cofactor and reagent (re)generation to direct photoactivation of enzymes enabling reactions unknown in nature. We highlight synthetically relevant transformations such as asymmetric reactions facilitated by the combination of light as energy source and enzymes’ catalytic power.

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“…11,12 FAP has a reported reaction quantum yield of greater than 80% and specificity for long chain fatty acids (C14-C18). [11][12][13] ADO catalyzes decarbonylation of butyraldehyde (C4) and this can be improved by enzyme engineering. 6 Likewise, we surmised that FAP could be engineered to decarboxylate the C4 compound butyric acid and other short chain volatile acids, to form propane and other hydrocarbon gases to enable their production at scale.…”

Section: <Insert Figure 1 Here>mentioning

confidence: 99%

Distributed Biomanufacturing of Liquefied Petroleum Gas

Hoeven

Jmx

Amer

et al. 2019

Preprint

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Liquefied Petroleum Gas (LPG) is a major domestic and transport fuel. Its combustion lessens NO x , greenhouse gas and particulates emissions compared to other fuels. Propane -the major constituent of LPG -is a clean, high value 'drop-in' fuel that can help governments develop integrated fuels and energy policies with low carbon burden, providing solutions to the multi-faceted challenges of future energy supply. We show that bio-LPG (bio-propane and bio-butane) can be produced by microbial conversion of waste volatile fatty acids that can be derived from anaerobic digestion, industrial waste, or CO 2 via photosynthesis. Bio-LPG production was achieved photo-catalytically, using biomass propagated from bioengineered bacteria including E. coli, Halomonas (in non-sterile seawater), and Synechocystis (photosynthetic). These fuel generation routes could be implemented rapidly in advanced and developing nations of the world to meet energy needs, global carbon reduction targets and clean air directives.[141words]

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Light‐Driven Enzymatic Decarboxylation of Fatty Acids

Cited by 159 publications

References 22 publications

Light‐Driven Kinetic Resolution of α‐Functionalized Carboxylic Acids Enabled by an Engineered Fatty Acid Photodecarboxylase

Light‐Driven Kinetic Resolution of α‐Functionalized Carboxylic Acids Enabled by an Engineered Fatty Acid Photodecarboxylase

Biocatalysis Fueled by Light: On the Versatile Combination of Photocatalysis and Enzymes

Distributed Biomanufacturing of Liquefied Petroleum Gas

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