Regulating Cofactor Balance In Vivo with a Synthetic Flavin Analogue

Tan, Zhuotao; Zhu, Chenjie; Fu, Jingwen; Zhang, Xiaowang; Li, Ming; Zhuang, Wei; Ying, Hanjie

doi:10.1002/anie.201810881

Cited by 14 publications

(6 citation statements)

References 44 publications

(11 reference statements)

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“…Moreover, considering that the absorption of these photocatalysts is in the range of visible light, still less damage to the biological system is ensured compared to photocatalysts activated by UV light. These photocatalyst systems may also have the potential to manipulate cofactor balance in vivo to regulate metabolic flux in a controlled way. , …”

Section: Resultsmentioning

confidence: 99%

“…These photocatalyst systems may also have the potential to manipulate cofactor balance in vivo to regulate metabolic flux in a controlled way. 48,49 ■ CONCLUSIONS Three amphiphilic polymers PEG 45 -b-PTTMNMA n (n = 8, 14, 21) with hydrophilic ratios (f PEG ) of 28.8, 19.6, and 14.4%, respectively, have been synthesized. They formed micelles, vesicle/micelle mixtures, and vesicles, respectively, using the nanoprecipitation method in water with dioxane as a cosolvent.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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AIE Polymer Micelle/Vesicle Photocatalysts Combined with Native Enzymes for Aerobic Photobiocatalysis

Zhang

Chen

2022

J. Am. Chem. Soc.

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Biocatalytic transformation has attracted increasing attention in the green synthesis of chemicals due to the diversity of enzymes, their high catalytic activities and specificities, and environmentally benign conditions. Most redox enzymes in nature are dependent on nicotinamide cofactors like β-nicotinamide adenine dinucleotide (NAD + )/reduced nicotinamide adenine dinucleotide (NADH). The use of solar energy, especially visible light, in the regeneration of cofactors through the combination of photocatalysis and biocatalysis provides an extraordinary opportunity to make complete green processes. However, the combination of photocatalysts and enzymes has been challenged by the rapid degradation and deactivation of the enzymatic material by photogenerated reactive oxygen species (ROS). Here, we design core−shell structured polymer micelles and vesicles with aggregation-induced emission (AIE) as visible-light-mediated photocatalysts for highly stable and recyclable photobiocatalysis under aerobic conditions. NAD + from NADH can be efficiently regenerated by the photoactive hydrophobic core of polymer micelles and the hydrophobic membrane of polymer vesicles, while the enzymatic material (glucose 1dehydrogenase) is screened from the attack of photogenerated ROS by the hydrophilic surface layer of polymer colloids. After at least 10 regeneration cycles, the enzyme keeps its active state; meanwhile, polymer micelles and vesicles maintain their photocatalytic activity. These polymer colloids show the potential to be developed for the implementation of industrially relevant photobiocatalytic systems.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

AIE Polymer Micelle/Vesicle Photocatalysts Combined with Native Enzymes for Aerobic Photobiocatalysis

Zhang

Chen

2022

J. Am. Chem. Soc.

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“…This is not surprising considering the natural occurrence of flavin in multicomponent systems but nevertheless opens new vistas in medicinal inorganic chemistry. [65] Another example of application of flavin mimics in cell media towards whole-cell biotransformation was reported [66] in which a synthetic flavin analogue was found to regulate cofactor balance in vivo. These…”

Section: Bioinspired Catalysis Using Flavin Redox Cofactorsmentioning

confidence: 99%

Nature is the Cure: Engineering Natural Redox Cofactors for Biomimetic and Bioinspired Catalysis

Murr

2019

ChemCatChem

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Metalloenzymes are nature's own catalysts and offer as such endless inspirational source for the chemists seeking selectivity in transformations. Metalloenzymes involved in oxidoreduction processes have specific subunits dedicated to electron and proton transfer, and these so‐called redox cofactors perform highly orchestrated redox events. This minireview offers a perspective on the development of biomimetic and bioinspired innovative approaches interfacing redox cofactors engineering with metal‐based catalysis, nanochemistry, light‐activation, supramolecular chemistry and artificial metalloenzymes to devise and build new synthetic systems using nature's finest electron transfer tools.

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“…Recently, inspired by flavin adenine dinucleotide–containing NADH [reduced form of nicotinamide adenine dinucleotide (NAD + )] oxidase catalyzing cofactor NAD(P) + [nicotinamide adenine dinucleotide (phosphate)] regeneration ( 25 ), we reported the feasibility of NAD(P) + regeneration system catalyzed by synthetic bridged flavin analog ( SBFA ) in vitro ( 26 ) and in vivo ( 27 ). Because of its excellent redox potential and aerobic oxidation characteristic, we speculated whether SBFA can be used as a biomimetic organocatalyst for the ADC reaction.…”

Section: Introductionmentioning

confidence: 99%

Cooperative chemoenzymatic synthesis of N-heterocycles via synergizing bio- with organocatalysis

Tan

Zhang

et al. 2022

Sci. Adv.

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Inspired by Nature’s ingenuity, considerable progress has been made in recent years to develop chemoenzymatic processes by the integration of environmentally friendly feature of biocatalysis with versatile reactivity of chemocatalysis. However, the current types of chemoenzymatic processes are relatively few and mostly rely on metal catalysts. Here, we report a previously unexplored cooperative chemoenzymatic system for the synthesis of N-heterocycles. Starting from alcohols and amines, benzimidazole, pyrazine, quinazoline, indole, and quinoline can be obtained in excellent yields in water with O 2 as the terminal oxidant. Synthetic bridged flavin analog is served as a bifunctional organocatalyst for the regeneration of cofactor nicotinamide adenine dinucleotide in the bioprocess and oxidative cyclodehydrogenation in the chemoprocess. Compared to the classical acceptorless dehydrogenative coupling strategy, being metal and base free, requiring only water as solvent, and not needing atmosphere protection were observed for the present method, exhibiting a favorable green and sustainable alternative.

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Regulating Cofactor Balance In Vivo with a Synthetic Flavin Analogue

Cited by 14 publications

References 44 publications

AIE Polymer Micelle/Vesicle Photocatalysts Combined with Native Enzymes for Aerobic Photobiocatalysis

AIE Polymer Micelle/Vesicle Photocatalysts Combined with Native Enzymes for Aerobic Photobiocatalysis

Nature is the Cure: Engineering Natural Redox Cofactors for Biomimetic and Bioinspired Catalysis

Cooperative chemoenzymatic synthesis of N-heterocycles via synergizing bio- with organocatalysis

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