Recent advances in photoenzymatic synthesis

MING Yang; CHEN Bin; HUANG Xiaoqiang

doi:10.12211/2096-8280.2022-056

您当前的位置：

首页 >

文章列表页 >

Recent advances in photoenzymatic synthesis

Invited Review | 更新时间：2025-03-20

- Recent advances in photoenzymatic synthesis
- Synthetic Biology Journal Vol. 4, Issue 4, Pages: 651-675(2023)
- 作者机构：
  
  南京大学化学化工学院，南京大学化学与生物医药创新研究院，配位化学国家重点实验室，江苏南京 210023
- 作者简介：
- 基金信息：
- DOI：10.12211/2096-8280.2022-056
  CLC： Q55;O62
- Received：10 October 2022，
  
  Revised：2022-12-06，
  
  Published：31 August 2023
- 稿件说明：
移动端阅览
明阳，陈彬，黄小强. 光酶催化合成进展［J］. 合成生物学， 2023， 4（4）： 651-675

MING Yang， CHEN Bin， HUANG Xiaoqiang. Recent advances in photoenzymatic synthesis［J］. Synthetic Biology Journal， 2023， 4（4）： 651-675
明阳，陈彬，黄小强. 光酶催化合成进展［J］. 合成生物学， 2023， 4（4）： 651-675 DOI： 10.12211/2096-8280.2022-056.

MING Yang， CHEN Bin， HUANG Xiaoqiang. Recent advances in photoenzymatic synthesis［J］. Synthetic Biology Journal， 2023， 4（4）： 651-675 DOI： 10.12211/2096-8280.2022-056.

摘要

酶催化具有绿色温和、高效高选择性的优势，在工业生产和技术研发等领域发挥着重要作用。然而，酶能催化的反应类型相对有限，难以满足未来绿色生物合成的需要。光催化已成为在温和反应条件下生成活性反应中间体的有效策略，但是光化学反应的选择性调控一直是个挑战性难题。结合光催化与酶催化的光酶催化合成，能够突破天然酶催化功能的局限，并为光化学领域的选择性调控难题提供新的解决方案，成为合成科学领域的研究热点之一。本文综述了光酶催化合成的最新研究进展，根据光酶的结合模式分成四部分讨论：光氧化还原实现辅因子再生、光催化剂-酶的协同或串联反应、光激发已知酶实现新转化、人工光酶。本文归纳了近年来光酶催化合成的代表性工作，重点分析光酶催化反应的化学机制和实现新生物转化的策略。与此同时，通过分析该领域当下面临的瓶颈，本文展望了光酶催化未来的发展方向，希望能够为光酶催化新转化的开发和更多高附加值化学品的绿色不对称合成提供参考。

Abstract

Biocatalysis has the advantages in terms of sustainability

efficiency

selectivities and evolvability

thus it plays a more and more important role in green and sustainable synthesis

both in industrial production and academic research. However

compared with the well-known privileged chemocatalysts

enzymes suffer from the relatively limited types of reactions it can catalyze

which is unable to meet the future needs of green biomanufacturing. On the other hand

photocatalysis has emerged as one of the most effective strategies for the generation of reactive chemical intermediates under mild conditions

thereby providing a fertile testing ground for inventing new chemistry. However

the light-generated organic intermediates

including radicals

radical ions

ions

as well as excited states

are highly reactive resulting in the difficulties of controlling the chemo- and stereo-selectivities. The integration of biocatalysis and photocatalysis created a cross-disciplinary area

namely photoenzymatic catalysis

which can not only provide a new solution to stereochemical control of photochemical transformations with the exquisite and tunable active site of enzymes

but also open a new avenue to expand the reactivity of enzymes with visible-light-excitation. In addition

photoenzymatic catalysis inherits the inherent advantages of biocatalysis and photocatalysis

such as mild reaction conditions

representing green and sustainable synthetic methods. We have witnessed the booming development of photoenzymatic catalysis during the past several years. In this review paper

the recent advances in this field are highlighted. According to the cooperative modes of photocatalysis and enzymes

this paper is divided into following four parts: photoredox-enabled cofactor regeneration systems

cascade/cooperative reactions combining enzymes with photocatalysts

unnatural transformations with photoactivable oxidoreductase

and artificial photoenzymes. In this paper

we summarize the representative works and emphasize on the catalytic mechanisms of photoenzymatic transformations as well as the strategies for realizing abiological transformations. At the end of this review

by analyzing the challenges of photoenzymatic synthesis

the future directions are prospected. We hope that this review can inspire the discovery of more novel photoenzymatic systems and ultimately spur the applications of photoenzymes in industrial productions of high value-added enantiopure chiral products.

关键词

Keywords

references

QU G , LI A T , ACEVEDO-ROCHA C G , et al . The crucial role of methodology development in directed evolution of selective enzymes [J ] . Angewandte Chemie International Edition , 2020 , 59 ( 32 ): 13204 - 13231 .

DEVINE P N , HOWARD R M , KUMAR R , et al . Extending the application of biocatalysis to meet the challenges of drug development [J ] . Nature Reviews Chemistry , 2018 , 2 ( 12 ): 409 - 421 .

SCHMID A , DORDICK J S , HAUER B , et al . Industrial biocatalysis today and tomorrow [J ] . Nature , 2001 , 409 ( 6817 ): 258 - 268 .

YI D , BAYER T , BADENHORST C P S , et al . Recent trends in biocatalysis [J ] . Chemical Society Reviews , 2021 , 50 ( 14 ): 8003 - 8049 .

PYSER J B , CHAKRABARTY S , ROMERO E O , et al . State-of-the-art biocatalysis [J ] . ACS Central Science , 2021 , 7 ( 7 ): 1105 - 1116 .

SURAJ C SAJEEV , SUMANT O . Enzymes market: opportunities and forecast [R/OL ] . 2022 , 2021 - 2031 . ( 2022-07-17 )[ 2022-11-01 ] . https://www.alliedmarketresearch.com/enzymes-market https://www.alliedmarketresearch.com/enzymes-market .

HANEFELD U , HOLLMANN F , PAUL C E . Biocatalysis making waves in organic chemistry [J ] . Chemical Society Reviews , 2022 , 51 ( 2 ): 594 - 627 .

PENG Y Z , CHEN Z C , XU J , et al . Recent advances in photobiocatalysis for selective organic synthesis [J ] . Organic Process Research & Development , 2022 , 26 ( 7 ): 1900 - 1913 .

CHEN K , ARNOLD F H . Engineering new catalytic activities in enzymes [J ] . Nature Catalysis , 2020 , 3 ( 3 ): 203 - 213 .

YOON T P , ISCHAY M A , DU J A . Visible light photocatalysis as a greener approach to photochemical synthesis [J ] . Nature Chemistry , 2010 , 2 ( 7 ): 527 - 532 .

CIAMICIAN G . The photochemistry of the future [J ] . Science , 1912 , 36 ( 926 ): 385 - 394 .

XU C P , RAVI ANUSUYADEVI P , AYMONIER C , et al . Nanostructured materials for photocatalysis [J ] . Chemical Society Reviews , 2019 , 48 ( 14 ): 3868 - 3902 .

HUANG X Q , MEGGERS E . Asymmetric photocatalysis with bis-cyclometalated rhodium complexes [J ] . Accounts of Chemical Research , 2019 , 52 ( 3 ): 833 - 847 .

BUZZETTI L , CRISENZA G E M , MELCHIORRE P . Mechanistic studies in photocatalysis [J ] . Angewandte Chemie International Edition , 2019 , 58 ( 12 ): 3730 - 3747 .

ZHANG J N , HU W P , CAO S , et al . Recent progress for hydrogen production by photocatalytic natural or simulated seawater splitting [J ] . Nano Research , 2020 , 13 ( 9 ): 2313 - 2322 .

FU J W , JIANG K X , QIU X Q , et al . Product selectivity of photocatalytic CO 2 reduction reactions [J ] . Materials Today , 2020 , 32 : 222 - 243 .

CHEN D J , CHENG Y L , ZHOU N , et al . Photocatalytic degradation of organic pollutants using TiO 2 -based photocatalysts: a review [J ] . Journal of Cleaner Production , 2020 , 268 : 121725 .

SILVESTRI S , FAJARDO A R , IGLESIAS B A . Supported porphyrins for the photocatalytic degradation of organic contaminants in water: a review [J ] . Environmental Chemistry Letters , 2022 , 20 ( 1 ): 731 - 771 .

XUAN J , HE X K , XIAO W J . Visible light-promoted ring-opening functionalization of three-membered carbo- and heterocycles [J ] . Chemical Society Reviews , 2020 , 49 ( 9 ): 2546 - 2556 .

YIN Y L , ZHAO X W , QIAO B K , et al . Cooperative photoredox and chiral hydrogen-bonding catalysis [J ] . Organic Chemistry Frontiers , 2020 , 7 ( 10 ): 1283 - 1296 .

CHAN A Y , PERRY I B , BISSONNETTE N B , et al . Metallaphotoredox: the merger of photoredox and transition metal catalysis [J ] . Chemical Reviews , 2022 , 122 ( 2 ): 1485 - 1542 .

BRIMIOULLE R , LENHART D , MATURI M M , et al . Enantioselective catalysis of photochemical reactions [J ] . Angewandte Chemie International Edition , 2015 , 54 ( 13 ): 3872 - 3890 .

WANG C F , LU Z . Catalytic enantioselective organic transformations via visible light photocatalysis [J ] . Organic Chemistry Frontiers , 2015 , 2 ( 2 ): 179 - 190 .

MEGGERS E . Asymmetric catalysis activated by visible light [J ] . Chemical Communications , 2015 , 51 ( 16 ): 3290 - 3301 .

HARRISON W , HUANG X Q , ZHAO H M . Photobiocatalysis for abiological transformations [J ] . Accounts of Chemical Research , 2022 , 55 ( 8 ): 1087 - 1096 .

GUO X W , OKAMOTO Y , SCHREIER M R , et al . Enantioselective synthesis of amines by combining photoredox and enzymatic catalysis in a cyclic reaction network [J ] . Chemical Science , 2018 , 9 ( 22 ): 5052 - 5056 .

ZHANG W Y , BUREK B O , FERNÁNDEZ-FUEYO E , et al . Selective activation of C—H bonds in a cascade process combining photochemistry and biocatalysis [J ] . Angewandte Chemie International Edition , 2017 , 56 ( 48 ): 15451 - 15455 .

ÖZGEN F F , RUNDA M E , SCHMIDT S . Photo-biocatalytic cascades: combining chemical and enzymatic transformations fueled by light [J ] . Chembiochem , 2021 , 22 ( 5 ): 790 - 806 .

蒋迎迎 , 曲戈 , 孙周通 . 机器学习助力酶定向进化 [J ] . 生物学杂志 , 2020 , 37 ( 4 ): 1 - 11 .

JIANG Y Y , QU G , SUN Z T . Machine learning-assisted enzyme directed evolution [J ] . Journal of Biology , 2020 , 37 ( 4 ): 1 - 11 .

WANG Y J , XUE P , CAO M F , et al . Directed evolution: methodologies and applications [J ] . Chemical Reviews , 2021 , 121 ( 20 ): 12384 - 12444 .

CHITNIS P R . PHOTOSYSTEM I: Function and physiology [J ] . Annual Review of Plant Physiology and Plant Molecular Biology , 2001 , 52 : 593 - 626 .

GAO J L , WANG H , YUAN Q P , et al . Structure and function of the photosystem supercomplexes [J ] . Frontiers in Plant Science , 2018 , 9 : 357 .

KAVAKLI I H , BARIS I , TARDU M , et al . The photolyase/cryptochrome family of proteins as DNA repair enzymes and transcriptional repressors [J ] . Photochemistry and Photobiology , 2017 , 93 ( 1 ): 93 - 103 .

SANCAR A . Structure and function of DNA photolyase and cryptochrome blue-light photoreceptors [J ] . Chemical Reviews , 2003 , 103 ( 6 ): 2203 - 2237 .

SORIGUÉ D , LÉGERET B , CUINÉ S , et al . An algal photoenzyme converts fatty acids to hydrocarbons [J ] . Science , 2017 , 357 ( 6354 ): 903 - 907 .

SORIGUÉ D , HADJIDEMETRIOU K , BLANGY S , et al . Mechanism and dynamics of fatty acid photodecarboxylase [J ] . Science , 2021 , 372 ( 6538 ): eabd5687 .

SCHMERMUND L , JURKAŠ V , ÖZGEN F F , et al . Photo-biocatalysis: biotransformations in the presence of light [J ] . ACS Catalysis , 2019 , 9 ( 5 ): 4115 - 4144 .

SEEL C J , GULDER T . Biocatalysis fueled by light: on the versatile combination of photocatalysis and enzymes [J ] . Chembiochem , 2019 , 20 ( 15 ): 1871 - 1897 .

LEE S H , CHOI D S , KUK S K , et al . Photobiocatalysis: activating redox enzymes by direct or indirect transfer of photoinduced electrons [J ] . Angewandte Chemie International Edition , 2018 , 57 ( 27 ): 7958 - 7985 .

张武元 , 袁波 , 曲戈 , 等 . 光促酶催化反应设计及生物合成应用 [J ] . 生物学杂志 , 2021 , 38 ( 5 ): 1 - 11 .

ZHANG W Y , YUAN B , QU G , et al . Photobiocatalytic reaction design and its biosynthetic applications [J ] . Journal of Biology , 2021 , 38 ( 5 ): 1 - 11 .

YUN C H , KIM J , HOLLMANN F , et al . Light-driven biocatalytic oxidation [J ] . Chemical Science , 2022 , 13 ( 42 ): 12260 - 12279 .

KIM J , LEE S H , TIEVES F , et al . Biocatalytic C=C bond reduction through carbon nanodot-sensitized regeneration of NADH analogues [J ] . Angewandte Chemie International Edition , 2018 , 57 ( 42 ): 13825 - 13828 .

SCHROEDER L , FRESE M , MÜLLER C , et al . Photochemically driven biocatalysis of halogenases for the green production of chlorinated compounds [J ] . ChemCatChem , 2018 , 10 ( 15 ): 3336 - 3341 .

CHENG Y Q , SHI J F , WU Y Z , et al . Intensifying electron utilization by surface-anchored Rh complex for enhanced nicotinamide cofactor regeneration and photoenzymatic CO 2 reduction [J ] . Research , 2021 , 2021 : 8175709 .

ZHANG S H , ZHANG Y S , CHEN Y , et al . Metal hydride-embedded titania coating to coordinate electron transfer and enzyme protection in photo-enzymatic catalysis [J ] . ACS Catalysis , 2021 , 11 ( 1 ): 476 - 483 .

JIA J S , HUO Q , YANG D , et al . Granum -inspired photoenzyme-coupled catalytic system via stacked polymeric carbon nitride [J ] . ACS Catalysis , 2021 , 11 ( 15 ): 9210 - 9220 .

SUN Y Y , SHI J F , WANG Z , et al . Thylakoid membrane-inspired capsules with fortified cofactor shuttling for enzyme-photocoupled catalysis [J ] . Journal of the American Chemical Society , 2022 , 144 ( 9 ): 4168 - 4177 .

STRIETH-KALTHOFF F , JAMES M J , TEDERS M , et al . Energy transfer catalysis mediated by visible light: principles, applications, directions [J ] . Chemical Society Reviews , 2018 , 47 ( 19 ): 7190 - 7202 .

ZHANG Y , LIU H Z , SHI Q S , et al . Enantiocomplementary synthesis of vicinal fluoro alcohols through photo-bio cascade reactions [J ] . Green Chemistry , 2022 , 24 ( 20 ): 7889 - 7893 .

SUN Y Y , LI W P , WANG Z , et al . General framework for enzyme-photo-coupled catalytic system toward carbon dioxide conversion [J ] . Current Opinion in Biotechnology , 2022 , 73 : 67 - 73 .

LITMAN Z C , WANG Y J , ZHAO H M , et al . Cooperative asymmetric reactions combining photocatalysis and enzymatic catalysis [J ] . Nature , 2018 , 560 ( 7718 ): 355 - 359 .

WANG Y J , HUANG X Q , HUI J S , et al . Stereoconvergent reduction of activated alkenes by a nicotinamide free synergistic photobiocatalytic system [J ] . ACS Catalysis , 2020 , 10 ( 16 ): 9431 - 9437 .

VERHO O , BÄCKVALL J E . Chemoenzymatic dynamic kinetic resolution: a powerful tool for the preparation of enantiomerically pure alcohols and amines [J ] . Journal of the American Chemical Society , 2015 , 137 ( 12 ): 3996 - 4009 .

BHAT V , WELIN E R , GUO X L , et al . Advances in stereoconvergent catalysis from 2005 to 2015: transition-metal-mediated stereoablative reactions, dynamic kinetic resolutions, and dynamic kinetic asymmetric transformations [J ] . Chemical Reviews , 2017 , 117 ( 5 ): 4528 - 4561 .

YANG Q , ZHAO F Q , ZHANG N , et al . Mild dynamic kinetic resolution of amines by coupled visible-light photoredox and enzyme catalysis [J ] . Chemical Communications , 2018 , 54 ( 100 ): 14065 - 14068 .

DEHOVITZ J S , LOH Y Y , KAUTZKY J A , et al . Static to inducibly dynamic stereocontrol: the convergent use of racemic β-substituted ketones [J ] . Science , 2020 , 369 ( 6507 ): 1113 - 1118 .

PIRNOT M T , RANKIC D A , MARTIN D B C , et al . Photoredox activation for the direct β-arylation of ketones and aldehydes [J ] . Science , 2013 , 339 ( 6127 ): 1593 - 1596 .

BIEGASIEWICZ K F , COOPER S J , EMMANUEL M A , et al . Catalytic promiscuity enabled by photoredox catalysis in nicotinamide-dependent oxidoreductases [J ] . Nature Chemistry , 2018 , 10 ( 7 ): 770 - 775 .

SANDOVAL B A , KURTOIC S I , CHUNG M M , et al . Photoenzymatic catalysis enables radical-mediated ketone reduction in ene-reductases [J ] . Angewandte Chemie International Edition , 2019 , 58 ( 26 ): 8714 - 8718 .

NAKANO Y , BLACK M J , MEICHAN A J , et al . Photoenzymatic hydrogenation of heteroaromatic olefins using 'ene'-reductases with photoredox catalysts [J ] . Angewandte Chemie International Edition , 2020 , 59 ( 26 ): 10484 - 10488 .

YE Y X , CAO J Z , OBLINSKY D G , et al . Using enzymes to tame nitrogen-centred radicals for enantioselective hydroamination [J ] . Nature Chemistry , 2023 , 15 ( 2 ): 206 - 212 .

LAUDER K , TOSCANI A , QI Y Y , et al . Photo-biocatalytic one-pot cascades for the enantioselective synthesis of 1, 3-mercaptoalkanol volatile sulfur compounds [J ] . Angewandte Chemie International Edition , 2018 , 57 ( 20 ): 5803 - 5807 .

YU Y , LIN R D , YAO Y , et al . Development of a metal- and oxidant-free enzyme-photocatalyst hybrid system for highly efficient C-3 acylation reactions of indoles with aldehydes [J ] . ACS Catalysis , 2022 , 12 ( 20 ): 12543 - 12554 .

DING X , DONG C L , GUAN Z , et al . Concurrent asymmetric reactions combining photocatalysis and enzyme catalysis: direct enantioselective synthesis of 2,2-disubstituted indol-3-ones from 2-arylindoles [J ] . Angewandte Chemie International Edition , 2019 , 58 ( 1 ): 118 - 124 .

BUREK B O , BORMANN S , HOLLMANN F , et al . Hydrogen peroxide driven biocatalysis [J ] . Green Chemistry , 2019 , 21 ( 12 ): 3232 - 3249 .

LÜTZ S , STECKHAN E , LIESE A . First asymmetric electroenzymatic oxidation catalyzed by a peroxidase [J ] . Electrochemistry Communications , 2004 , 6 ( 6 ): 583 - 587 .

ZHANG W Y , FERNÁNDEZ-FUEYO E , NI Y , et al . Selective aerobic oxidation reactions using a combination of photocatalytic water oxidation and enzymatic oxyfunctionalizations [J ] . Nature Catalysis , 2018 , 1 ( 1 ): 55 - 62 .

YUAN B , MAHOR D , FEI Q , et al . Water-soluble anthraquinone photocatalysts enable methanol-driven enzymatic halogenation and hydroxylation reactions [J ] . ACS Catalysis , 2020 , 10 ( 15 ): 8277 - 8284 .

ZHANG W Y , MA M , HUIJBERS M M E , et al . Hydrocarbon synthesis via photoenzymatic decarboxylation of carboxylic acids [J ] . Journal of the American Chemical Society , 2019 , 141 ( 7 ): 3116 - 3120 .

XU J , HU Y J , FAN J J , et al . Light-driven kinetic resolution of α-functionalized carboxylic acids enabled by an engineered fatty acid photodecarboxylase [J ] . Angewandte Chemie International Edition , 2019 , 58 ( 25 ): 8474 - 8478 .

LI D Y , WU Q , REETZ M T . Focused rational iterative site-specific mutagenesis (FRISM) [J ] . Methods in Enzymology , 2020 , 643 : 225 - 242 .

XU J , FAN J J , LOU Y J , et al . Light-driven decarboxylative deuteration enabled by a divergently engineered photodecarboxylase [J ] . Nature Communications , 2021 , 12 : 3983 .

LI D Y , HAN T , XUE J D , et al . Engineering fatty acid photodecarboxylase to enable highly selective decarboxylation of trans fatty acids [J ] . Angewandte Chemie International Edtion , 2021 , 60 ( 38 ): 20695 - 20699 .

GE R , ZHANG P P , DONG X T , et al . Photobiocatalytic decarboxylation for the synthesis of fatty epoxides from renewable fatty acids [J ] . ChemSusChem , 2022 , 15 ( 20 ): e202201275 .

AMER M , WOJCIK E Z , SUN C H , et al . Low carbon strategies for sustainable bio-alkane gas production and renewable energy [J ] . Energy & Environmental Science , 2020 , 13 ( 6 ): 1818 - 1831 .

BRUDER S , MOLDENHAUER E J , LEMKE R D , et al . Drop-in biofuel production using fatty acid photodecarboxylase from Chlorella variabilis in the oleaginous yeast Yarrowia lipolytica [J ] . Biotechnology for Biofuels , 2019 , 12 : 202 .

XU W H , MOU K H , ZHOU H N , et al . Transformation of triolein to biogasoline by photo-chemo-biocatalysis [J ] . Green Chemistry , 2022 , 24 ( 17 ): 6589 - 6598 .

SELLÉS VIDAL L , KELLY C L , MORDAKA P M , et al . Review of NAD(P)H-dependent oxidoreductases: properties, engineering and application [J ] . Biochimica et Biophysica Acta-Proteins and Proteomics , 2018 , 1866 ( 2 ): 327 - 347 .

TOOGOOD H S , SCRUTTON N S . Discovery, characterisation, engineering and applications of ene reductases for industrial biocatalysis [J ] . ACS Catalysis , 2019 , 8 ( 4 ): 3532 - 3549 .

MULLIKEN R S . Molecular compounds and their spectra. Ⅱ [J ] . Journal of the American Chemical Society , 1952 , 74 ( 3 ): 811 - 824 .

CRISENZA G E M , MAZZARELLA D , MELCHIORRE P . Synthetic methods driven by the photoactivity of electron donor-acceptor complexes [J ] . Journal of the American Chemical Society , 2020 , 142 ( 12 ): 5461 - 5476 .

EMMANUEL M A , GREENBERG N R , OBLINSKY D G , et al . Accessing non-natural reactivity by irradiating nicotinamide-dependent enzymes with light [J ] . Nature , 2016 , 540 ( 7633 ): 414 - 417 .

PENG Y Z , WANG Z G , CHEN Y , et al . Photoinduced promiscuity of cyclohexanone monooxygenase for the enantioselective synthesis of α-fluoroketones [J ] . Angewandte Chemie International Edtion , 2022 , 61 ( 50 ): e202211199 .

HUANG X Q , FENG J Q , CUI J W , et al . Photoinduced chemomimetic biocatalysis for enantioselective intermolecular radical conjugate addition [J ] . Nature Catalysis , 2022 , 5 ( 7 ): 586 - 593 .

XU J , CEN Y X , SINGH W , et al . Stereodivergent protein engineering of a lipase to access all possible stereoisomers of chiral esters with two stereocenters [J ] . Journal of the American Chemical Society , 2019 , 141 ( 19 ): 7934 - 7945 .

BIEGASIEWICZ K F , COOPER S J , GAO X , et al . Photoexcitation of flavoenzymes enables a stereoselective radical cyclization [J ] . Science , 2019 , 364 ( 6446 ): 1166 - 1169 .

LAGUERRE N , RIEHL P S , OBLINSKY D G , et al . Radical termination via β-scission enables photoenzymatic allylic alkylation using "ene"-reductases [J ] . ACS Catalysis , 2022 , 12 ( 15 ): 9801 - 9805 .

BLACK M J , BIEGASIEWICZ K F , MEICHAN A J , et al . Asymmetric redox-neutral radical cyclization catalysed by flavin-dependent 'ene'-reductases [J ] . Nature Chemistry , 2020 , 12 ( 1 ): 71 - 75 .

SANDOVAL B A , CLAYMAN P D , OBLINSKY D G , et al . Photoenzymatic reductions enabled by direct excitation of flavin-dependent 'ene'-reductases [J ] . Journal of the American Chemical Society , 2021 , 143 ( 4 ): 1735 - 1739 .

HUANG X Q , WANG B J , WANG Y J , et al . Photoenzymatic enantioselective intermolecular radical hydroalkylation [J ] . Nature , 2020 , 584 ( 7819 ): 69 - 74 .

PAGE C G , COOPER S J , DEHOVITZ J S , et al . Quaternary charge-transfer complex enables photoenzymatic intermolecular hydroalkylation of olefins [J ] . Journal of the American Chemical Society , 2021 , 143 ( 1 ): 97 - 102 .

FU H G , LAM H , EMMANUEL M A , et al . Ground-state electron transfer as an initiation mechanism for biocatalytic C—C bond forming reactions [J ] . Journal of the American Chemical Society , 2021 , 143 ( 25 ): 9622 - 9629 .

FU H G , CAO J Z , QIAO T Z , et al . An asymmetric sp 3 -sp 3 cross-electrophile coupling using 'ene'-reductases [J ] . Nature , 2022 , 610 ( 7931 ): 302 - 307 .

GU Y F , ELLIS-GUARDIOLA K , SRIVASTAVA P , et al . Preparation, characterization, and oxygenase activity of a photocatalytic artificial enzyme [J ] . Chembiochem , 2015 , 16 ( 13 ): 1880 - 1883 .

ZUBI Y S , LIU B Q , GU Y F , et al . Controlling the optical and catalytic properties of artificial metalloenzyme photocatalysts using chemogenetic engineering [J ] . Chemical Science , 2022 , 13 ( 5 ): 1459 - 1468 .

SOSA V , MELKIE M , SULCA C , et al . Selective light-driven chemoenzymatic trifluoromethylation/hydroxylation of substituted arenes [J ] . ACS Catalysis , 2018 , 8 ( 3 ): 2225 - 2229 .

SCHWOCHERT T D , CRUZ C L , WATTERS J W , et al . Design and evaluation of artificial hybrid photoredox biocatalysts [J ] . Chembiochem , 2020 , 21 ( 21 ): 3146 - 3150 .

CESANA P T , LI B X , SHEPARD S G , et al . A biohybrid strategy for enabling photoredox catalysis with low-energy light [J ] . Chem , 2022 , 8 ( 1 ): 174 - 185 .

CESANA P T , PAGE C G , HARRIS D , et al . Photoenzymatic catalysis in a new light: Gluconobacter "ene"-reductase conjugates possessing high-energy reactivity with tunable low-energy excitation [J ] . Journal of the American Chemical Society , 2022 , 144 ( 38 ): 17516 - 17521 .

YU Y , LIU X H , WANG J Y . Expansion of redox chemistry in designer metalloenzymes [J ] . Accounts of Chemical Research , 2019 , 52 ( 3 ): 557 - 565 .

LIU X H , LIU P C , LI H J , et al . Excited-state intermediates in a designer protein encoding a phototrigger caught by an X-ray free-electron laser [J ] . Nature Chemistry , 2022 , 14 ( 9 ): 1054 - 1060 .

ZHENG D D , TAO M , YU L J , et al . Ultrafast photoinduced electron transfer in a photosensitizer protein [J ] . CCS Chemistry , 2022 , 4 ( 4 ): 1217 - 1223 .

LIU X H , KANG F Y , HU C , et al . A genetically encoded photosensitizer protein facilitates the rational design of a miniature photocatalytic CO 2 -reducing enzyme [J ] . Nature Chemistry , 2018 , 10 ( 12 ): 1201 - 1206 .

FU Y , HUANG J , WU Y Z , et al . Biocatalytic cross-coupling of aryl halides with a genetically engineered photosensitizer artificial dehalogenase [J ] . Journal of the American Chemical Society , 2021 , 143 ( 2 ): 617 - 622 .

SUN N N , HUANG J J , QIAN J Y , et al . Enantioselective [2+2]-cycloadditions with triplet photoenzymes [J ] . Nature , 2022 , 611 ( 7937 ): 715 - 720 .

ROELFES G . LmrR: A privileged scaffold for artificial metalloenzymes [J ] . Accounts of Chemical Research , 2019 , 52 ( 3 ): 545 - 556 .

TRIMBLE J S , CRAWSHAW R , HARDY F J , et al . A designed photoenzyme for enantioselective [2+2]cycloadditions [J ] . Nature , 2022 , 611 ( 7937 ): 709 - 714 .

SIEGEL J B , ZANGHELLINI A , LOVICK H M , et al . Computational design of an enzyme catalyst for a stereoselective bimolecular Diels-Alder reaction [J ] . Science , 2010 , 329 ( 5989 ): 309 - 313 .

Views

下载量

CSCD

Alert me when the article has been cited

提交

Tools

Publicity Resources

Recent advances in chemically driven enantioselective photobiocatalysis

Halogenases in biocatalysis: advances in mechanism elucidation, directed evolution, and green manufacturing

AI-enabled directed evolution for protein engineering and optimization

Related Author

HUANG Xiaoqiang

CHEN Bin

MING Yang

ZHONG Fangrui

FU Yu

ZHONG Fangrui

ZHANG Yimin

WANG Qinhong

Related Institution

State Key Laboratory of Coordination Chemistry， Chemistry and Biomedicine Innovation Center，School of Chemistry and Chemical Engineering， Nanjing University

Hubei Key Laboratory of Bioinorganic Chemistry & Materia Medica， Hubei Engineering Research Center for Biomaterials and Medical Protective Materials， School of Chemistry and Chemical Engineering， Huazhong University of Science and Technology （HUST）

College of Pharmacy， Shenzhen Technology University

Hubei Engineering Research Center for Biomaterials and Medical Protective Materials， Hubei Key Laboratory of Bioinorganic Chemistry & Materia Medica， School of Chemistry and Chemical Engineering， Huazhong University of Science and Technology （HUST）

School of Life Sciences， Qufu Normal University， Qufu

⁰