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Open accessJournal ArticleDOI: 10.1002/CBIC.202000587

Photo-biocatalytic Cascades: Combining Chemical and Enzymatic Transformations Fueled by Light.

02 Mar 2021-ChemBioChem (WILEY-V C H VERLAG GMBH)-Vol. 22, Iss: 5, pp 790-806
Abstract: In the field of green chemistry, light - an attractive natural agent - has received particular attention for driving biocatalytic reactions. Moreover, the implementation of light to drive (chemo)enzymatic cascade reactions opens up a golden window of opportunities. However, there are limitations to many current examples, mostly associated with incompatibility between the enzyme and the photocatalyst. Additionally, the formation of reactive radicals upon illumination and the loss of catalytic activities in the presence of required additives are common observations. As outlined in this review, the main question is how to overcome current challenges to the exploitation of light to drive (chemo)enzymatic transformations. First, we highlight general concepts in photo-biocatalysis, then give various examples of photo-chemoenzymatic (PCE) cascades, further summarize current synthetic examples of PCE cascades and discuss strategies to address the limitations.

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Open access
08 Jul 2018-
Abstract: Abstract A mild and selective C(sp3)−H aerobic oxidation enabled by decatungstate photocatalysis has been developed. The reaction can be significantly improved in a microflow reactor enabling the safe use of oxygen and enhanced irradiation of the reaction mixture. Our method allows for the oxidation of both activated and unactivated C−H bonds (30 examples). The ability to selectively oxidize natural scaffolds, such as (−)‐ambroxide, pregnenolone acetate, (+)‐sclareolide, and artemisinin, exemplifies the utility of this new method.

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Topics: Photocatalysis (55%)

70 Citations


Open accessJournal ArticleDOI: 10.1039/D0CS01575J
Dong Yi1, Thomas Bayer1, Christoffel P. S. Badenhorst1, Shuke Wu1  +3 moreInstitutions (1)
Abstract: Biocatalysis has undergone revolutionary progress in the past century. Benefited by the integration of multidisciplinary technologies, natural enzymatic reactions are constantly being explored. Protein engineering gives birth to robust biocatalysts that are widely used in industrial production. These research achievements have gradually constructed a network containing natural enzymatic synthesis pathways and artificially designed enzymatic cascades. Nowadays, the development of artificial intelligence, automation, and ultra-high-throughput technology provides infinite possibilities for the discovery of novel enzymes, enzymatic mechanisms and enzymatic cascades, and gradually complements the lack of remaining key steps in the pathway design of enzymatic total synthesis. Therefore, the research of biocatalysis is gradually moving towards the era of novel technology integration, intelligent manufacturing and enzymatic total synthesis.

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9 Citations


Journal ArticleDOI: 10.1038/S41570-021-00265-6
01 May 2021-
Abstract: Light-powered catalysis has found broad utility as a chemical transformation strategy, with widespread impact on energy, environment, drug discovery and human health. A noteworthy application impacting human health is light-induced sensitization of cofactors for photodynamic therapy in cancer treatment. The clinical adoption of this photosensitization approach has inspired the search for other photochemical methods, such as photoredox catalysis, to influence biological discovery. Over the past decade, light-mediated catalysis has enabled the discovery of valuable synthetic transformations, propelling it to become a highly utilized chemical synthesis strategy. The reaction components required to achieve a photoredox reaction are identical to photosensitization (catalyst, light source and substrate), making it ideally suited for probing biological environments. In this Review, we discuss the therapeutic application of photosensitization and advancements made in developing next-generation catalysts. We then highlight emerging uses of photoredox catalytic methods for protein bioconjugation and probing complex cellular environments in living cells. Photocatalysis is widely used in numerous fields, including chemistry and biology. This Review highlights the impact of photosensitization and photoredox photocatalysis within therapeutic development, bioconjugation and for probing complex cellular environments.

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Topics: Photoredox catalysis (53%)

7 Citations


Journal ArticleDOI: 10.1016/J.COGSC.2021.100496
Abstract: Using light for biocatalysis is a relatively new and expanding research field. Because of the ever-increasing number of publications, this review highlights developments in the field of photobiocatalysis published in the past two years. We introduce the topic briefly and list most of the review articles appeared so far. Afterward, we devote special attention to the most interesting and relevant key articles in the field of in vitro photobiocatalysis, and briefly, we describe novel discoveries in photobiocatalytic cascades and in strict light-dependent enzymes. Finally, we outline developments in the next decade in the conclusions and future perspectives part.

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3 Citations


Journal ArticleDOI: 10.1002/ANIE.202015215
14 Jun 2021-Angewandte Chemie
Abstract: The combination of gold(I) and enzyme catalysis is used in a two-step approach, including Meyer-Schuster rearrangement of a series of readily available propargylic alcohols followed by stereoselective bioreduction of the corresponding allylic ketone intermediates, to provide optically pure β,β-disubstituted allylic alcohols. This cascade involves a gold N-heterocyclic carbene and an enzyme, demonstrating the compatibility of both catalyst types in aqueous medium under mild reaction conditions. The combination of [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene][bis(trifluoromethanesulfonyl)-imide]gold(I) (IPrAuNTf2 ) and a selective alcohol dehydrogenase (ADH-A from Rhodococcus ruber, KRED-P1-A12 or KRED-P3-G09) led to the synthesis of a series of optically active (E)-4-arylpent-3-en-2-ols in good yields (65-86 %). The approach was also extended to various 2-hetarylpent-3-yn-2-ol, hexynol, and butynol derivatives. The use of alcohol dehydrogenases of opposite selectivity led to the production of both allyl alcohol enantiomers (93->99 % ee) for a broad panel of substrates.

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Topics: Allyl alcohol (59%), Allylic rearrangement (57%), Meyer–Schuster rearrangement (53%) ... show more

2 Citations


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145 results found


Open accessJournal ArticleDOI: 10.1021/ACS.CHEMREV.6B00018
25 Apr 2016-Chemical Reviews
Abstract: The interaction between an electronically excited photocatalyst and an organic molecule can result in the genertion of a diverse array of reactive intermediates that can be manipulated in a variety of ways to result in synthetically useful bond constructions. This Review summarizes dual-catalyst strategies that have been applied to synthetic photochemistry. Mechanistically distinct modes of photocatalysis are discussed, including photoinduced electron transfer, hydrogen atom transfer, and energy transfer. We focus upon the cooperative interactions of photocatalysts with redox mediators, Lewis and Bronsted acids, organocatalysts, enzymes, and transition metal complexes.

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1,299 Citations



Journal ArticleDOI: 10.1039/C3CS60282F
Zhen Guo1, Bin Liu1, Qinghong Zhang2, Weiping Deng2  +3 moreInstitutions (2)
Abstract: Oxidation catalysis not only plays a crucial role in the current chemical industry for the production of key intermediates such as alcohols, epoxides, aldehydes, ketones and organic acids, but also will contribute to the establishment of novel green and sustainable chemical processes. This review is devoted to dealing with selective oxidation reactions, which are important from the viewpoint of green and sustainable chemistry and still remain challenging. Actually, some well-known highly challenging chemical reactions involve selective oxidation reactions, such as the selective oxidation of methane by oxygen. On the other hand some important oxidation reactions, such as the aerobic oxidation of alcohols in the liquid phase and the preferential oxidation of carbon monoxide in hydrogen, have attracted much attention in recent years because of their high significance in green or energy chemistry. This article summarizes recent advances in the development of new catalytic materials or novel catalytic systems for these challenging oxidation reactions. A deep scientific understanding of the mechanisms, active species and active structures for these systems are also discussed. Furthermore, connections among these distinct catalytic oxidation systems are highlighted, to gain insight for the breakthrough in rational design of efficient catalytic systems for challenging oxidation reactions.

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Topics: Alcohol oxidation (57%), Catalytic oxidation (56%)

471 Citations


Journal ArticleDOI: 10.1126/SCIENCE.AAF2091
22 Apr 2016-Science
Abstract: The splitting of dinitrogen (N2) and reduction to ammonia (NH3) is a kinetically complex and energetically challenging multistep reaction. In the Haber-Bosch process, N2 reduction is accomplished at high temperature and pressure, whereas N2 fixation by the enzyme nitrogenase occurs under ambient conditions using chemical energy from adenosine 5'-triphosphate (ATP) hydrolysis. We show that cadmium sulfide (CdS) nanocrystals can be used to photosensitize the nitrogenase molybdenum-iron (MoFe) protein, where light harvesting replaces ATP hydrolysis to drive the enzymatic reduction of N2 into NH3 The turnover rate was 75 per minute, 63% of the ATP-coupled reaction rate for the nitrogenase complex under optimal conditions. Inhibitors of nitrogenase (i.e., acetylene, carbon monoxide, and dihydrogen) suppressed N2 reduction. The CdS:MoFe protein biohybrids provide a photochemical model for achieving light-driven N2 reduction to NH3.

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Topics: Nitrogenase (55%), ATP hydrolysis (51%)

467 Citations


Journal ArticleDOI: 10.1021/JA208760J
Chelsea A. Huff1, Melanie S. Sanford1Institutions (1)
Abstract: This communication demonstrates the homogeneous hydrogenation of CO2 to CH3OH via cascade catalysis. Three different homogeneous catalysts, (PMe3)4Ru(Cl)(OAc), Sc(OTf)3, and (PNN)Ru(CO)(H), operate in sequence to promote this transformation.

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Topics: Homogeneous catalysis (67%), Catalysis (54%)

430 Citations


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