Photoenzymatic Approaches in Organic Synthesis

Chen, Jie; Guan, Zhi; He, Yan‐Hong

doi:10.1002/ajoc.201900427

Cited by 23 publications

(14 citation statements)

References 36 publications

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“…The combination of enzymatic catalysis and photochemistry provides numerous perspectives for organic synthesis [110][111][112][113]. This strategy is also an important element of sustainable (green) chemistry.…”

Section: Photochemically Supported Enzymatic Reactionsmentioning

confidence: 99%

Enantioselective synthesis of heterocyclic compounds using photochemical reactions

Hoffmann

2021

Photochem Photobiol Sci

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Different methods for the direct enantioselective photochemical synthesis of heterocycles are presented. Currently, asymmetric catalysis with templates involving hydrogen bonds or metal complexes is intensively investigated. Enzyme catalysis can be simplified under photochemical conditions. For example, in multi enzyme systems, one or more enzyme catalytic steps can be replaced by simple photochemical reactions. Chiral induction in photochemical reactions performed with homochiral crystals is highly efficient. Such reactions can also be carried out with crystalline inclusion complexes. Inclusion of a photochemical substrate and an enantiopure compound in zeolites also leads to enantioselective compounds. In all these methods, the conformational mobility of the photochemical substrates is reduced or controlled. Memory of chirality is a particular case in which a chiral information is temporally lost but the rigid conformations stabilize the molecular structure which leads to the formation of enantiopure compounds. Such studies allows a profound understanding on how particular conformations determine the configuration of the final products.

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Section: Photochemically Supported Enzymatic Reactionsmentioning

confidence: 99%

Enantioselective synthesis of heterocyclic compounds using photochemical reactions

Hoffmann

2021

Photochem Photobiol Sci

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“…As a consequence, researchers in synthetic organic chemistry work day by day in the development of processes that are friendly to the environment and that may be achieved through photo-organocatalytic processes; that is, by the use of small molecules that interact with light promoting chemical reactions [ 141 ]. Photocatalysis is therefore a topic of current interest and has given rise to many publications [ 142 , 143 , 144 ]. However, there are very few reports of the use of this technique under solvent-free conditions.…”

Section: Photocatalysis Under Solvent-free Conditionsmentioning

confidence: 99%

Novel Methodologies for Chemical Activation in Organic Synthesis under Solvent-Free Reaction Conditions

Avila‐Ortiz

Juaristi

2020

Molecules

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One central challenge for XXI century chemists is the development of sustainable processes that do not represent a risk either to humanity or to the environment. In this regard, the search for more efficient and clean alternatives to achieve the chemical activation of molecules involved in chemical transformations has played a prominent role in recent years. The use of microwave or UV-Vis light irradiation, and mechanochemical activation is already widespread in many laboratories. Nevertheless, an additional condition to achieve “green” processes comes from the point of view of so-called atom economy. The removal of solvents from chemical reactions generally leads to cleaner, more efficient and more economical processes. This review presents several illustrative applications of the use of sustainable protocols in the synthesis of organic compounds under solvent-free reaction conditions.

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“…[6] However, most of the examples combing photo-/electro-and biocatalysis are focusing on the cofactor recycling or cofactor replacement with light irradiation. [7][8][9][10] Notably, examples of photoenzymes by direct light activation are quite rare but desirable.…”

Section: Introductionmentioning

confidence: 99%

“…For example, asymmetric organocatalytic C−C bond‐forming reactions have been combined with redox enzymatic biotransformation, [5] (3) Combination of photo‐/electro‐(chemistry and catalysis) and biocatalysis, which is the most attractive approach to promote electron transfer, thus enables the development of green and sustainable chemistry [6] . However, most of the examples combing photo‐/electro‐and biocatalysis are focusing on the cofactor recycling or cofactor replacement with light irradiation [7–10] . Notably, examples of photoenzymes by direct light activation are quite rare but desirable.…”

Section: Introductionmentioning

confidence: 99%

Light‐Driven Enzymatic Decarboxylation of Dicarboxylic Acids

et al. 2021

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Photodecarboxylase from Chlorella variabillis ( Cv FAP) is one of the three known light‐activated enzymes that catalyzes the decarboxylation of fatty acids into the corresponding C1‐shortened alkanes. Although the substrate scope of Cv FAP has been altered by protein engineering and decoy molecules, it is still limited to mono‐fatty acids. Our studies demonstrate for the first time that long chain dicarboxylic acids can be converted by Cv FAP. Notably, the conversion of dicarboxylic acids to alkanes still represents a chemically very challenging reaction. Herein, the light‐driven enzymatic decarboxylation of dicarboxylic acids to the corresponding (C2‐shortened) alkanes using Cv FAP is described. A series of dicarboxylic acids is decarboxylated into alkanes in good yields by means of this approach, even for the preparative scales. Reaction pathway studies show that mono‐fatty acids are formed as the intermediate products before the final release of C2‐shortened alkanes. In addition, the thermostability, storage stability, and recyclability of Cv FAP for decarboxylation of dicarboxylic acids are well evaluated. These results represent an advancement over the current state‐of‐the‐art.

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Photoenzymatic Approaches in Organic Synthesis

Cited by 23 publications

References 36 publications

Enantioselective synthesis of heterocyclic compounds using photochemical reactions

Enantioselective synthesis of heterocyclic compounds using photochemical reactions

Novel Methodologies for Chemical Activation in Organic Synthesis under Solvent-Free Reaction Conditions

Light‐Driven Enzymatic Decarboxylation of Dicarboxylic Acids

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