Article
Chemistry, Multidisciplinary
Christopher J. J. Hall, William R. F. Goundry, Timothy J. Donohoe
Summary: Enantiopure 1,2-amino alcohols derived from abundant amino acids were used in C-C bond-forming hydrogen-borrowing alkylation reactions for the first time. The use of Ph*COMe aryl ketone facilitated the reactions, preventing racemisation of the amine stereocentre. The Ph* and trityl groups could be easily cleaved in one pot to give GABA products without further purification, allowing the two steps to be performed in sequence without isolation of the hydrogen-borrowing intermediate, eliminating the need for column chromatography.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
Pawel Borowiecki, Aleksandra Rudzka, Tamara Reiter, Wolfgang Kroutil
Summary: This study reports a chemoenzymatic route towards xanthine-based enantiomerically pure active pharmaceutical ingredients using recombinant short-chain ADHs, achieving excellent enantiomeric excess and high yields for both (R)- and (S)-enantiomers. The biocatalytic method demonstrated in this work is straightforward and practical for the manufacturing of these pharmaceuticals.
BIOORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yu Li, Na Hu, Zefei Xu, Yunfeng Cui, Jinhui Feng, Peiyuan Yao, Qiaqing Wu, Dunming Zhu, Yanhe Ma
Summary: The enzymatic asymmetric reductive amination process can be used to convert simple aldehydes and amines into chiral N-substituted 1,2-amino alcohols, providing an environmentally friendly and economical method.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Xiaoyang Li, Yufei Cao, Jiarong Xiong, Jun Li, Hai Xiao, Xinyang Li, Qingqiang Gou, Jun Ge
Summary: Combining enzymatic and single-metal-atom catalysis shows promise for green chemical synthesis. This study presents a one-pot chemoenzymatic cascade reaction for the asymmetric synthesis of (R)-1-(4-biphenyl) ethanol, using a highly active and selective enzyme-metal-single-atom hybrid as the catalyst. The Pd single atoms anchored lipase (Pd1/CALB-P) efficiently drives cascade reactions in aqueous solution, achieving facile synthesis of chiral biaryl alcohols.
CHINESE JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Physical
Takehiro Matsuyama, Takafumi Yatabe, Tomohiro Yabe, Kazuya Yamaguchi
Summary: A versatile 1,2-diketone decarbonylation to produce diaryl ketones was achieved using a CeO2-supported Au-Pd alloy nanoparticle catalyst. The high catalytic performance was attributed to the promotion of reductive elimination by electron-deficient Pd(0) species interacting strongly with CeO2 and the suppression of catalyst deactivation through Pd alloying with Au.
Article
Chemistry, Physical
Takehiro Matsuyama, Takafumi Yatabe, Tomohiro Yabe, Kazuya Yamaguchi
Summary: This study reports a versatile decarbonylation of diaryl 1,2-diketones to afford diaryl ketones using a CeO2-supported Au-Pd alloy nanoparticle catalyst. Through thorough characterization of the catalyst, kinetic evaluation, and control experiments, it was found that the high catalytic performance is attributed to the interaction of electron-deficient Pd(0) species with CeO2 and the suppression of catalyst deactivation by alloying Pd with Au.
Article
Chemistry, Multidisciplinary
Minghui Zhu, Qinglong Zhang, Weiwei Zi
Summary: The study presents a dual-metal catalyzed diastereodivergent coupling method for the synthesis of beta-amino alcohols with multiple stereoisomers, enabling the concise preparation of natural products such as mycestericins F and G.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Balaji Sundara Sekar, Jiwei Mao, Benedict Ryan Lukito, Zilong Wang, Zhi Li
Summary: Enzyme cascades were developed to convert styrene into enantiopure (R)- and (S)-2-phenylglycinols, as well as other substituted styrenes and indene into substituted phenylglycinols and 1-amino-2-indanol with high enantioselectivity. Enantioselective enzyme cascades were also developed to produce (R)- and (S)-2-phenylglycinols from bio-based L-phenylalanine. Combining L-phenylalanine biosynthesis pathway with enantioselective cascade in one strain or coupled strains enabled the synthesis of (R)- and (S)-2-phenylglycinols from renewable feedstocks, enhancing production from glucose and glycerol.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Allwin D. McDonald, Samantha K. Bruffy, Aadhishre T. Kasat, Andrew R. Buller
Summary: In this study, we used a substrate multiplexed screening approach to improve the substrate scope overlap in biocatalytic cascades for the synthesis of chiral 1,2-amino alcohols. By engineering the activity of enzymes, we achieved selective and efficient synthesis of enantiopure products in a one-pot cascade reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Paula Oroz, Claudio D. Navo, Alberto Avenoza, Jesus H. Busto, Francisco Corzana, Gonzalo Jimenez-Oses, Jesus M. Peregrina
Summary: The study introduces a novel method for the chemo- and diastereoselective 1,4-conjugate additions of Se-nucleophiles to a chiral bicyclic dehydroalanine, offering a promising route for the synthesis of enantiomerically pure selenocysteine derivatives with high potential for chemical biology applications.
Article
Chemistry, Multidisciplinary
Edwin Avila, Christos Nixarlidis, Young-Seok Shon
Summary: The catalytic activity and selectivity of two different water-soluble palladium nanoparticles capped with different ligands were investigated. The nanoparticles exhibited high regioselectivity in transforming allyl benzene to 3-phenylpropanal, and the yields reached up to 83%. The presence of benzylic hydrogen played a crucial role in the formation of a p-allyl Pd intermediate and the anti-Markovnikov addition of H2O.
Article
Nanoscience & Nanotechnology
Viktor Sabadasch, Maxim Dirksen, Pascal Fandrich, Julian Cremer, Niklas Biere, Dario Anselmetti, Thomas Hellweg
Summary: In this study, palladium-loaded smart membranes made by UV cross-linking of thermoresponsive microgels were prepared as reusable, catalytically active materials. The membranes were examined for their coverage of a supporting mesh and their Young modulus. The catalytic activity of the membrane was compared with suspended colloidal nanoparticle microgel hybrids, and the membrane showed lower catalytic activity but allowed for easy separation and recycling of the catalyst. The results demonstrate the feasibility and durability of depositing catalytically active inter-cross-linked microgel particles on commercial nylon meshes for scaling up continuous industrial processes.
ACS APPLIED MATERIALS & INTERFACES
(2022)
Article
Engineering, Environmental
Xiaoyang Li, Xinyu Hu, Yida Qiao, Tianying Lu, Yunxiu Bai, Jiarong Xiong, Xinyang Li, Qingqiang Gou, Jun Ge
Summary: By constructing an enzyme-bimetallic hybrid catalyst on cross-linked lipase aggregates, the intrinsic incompatibility between enzyme and chemical catalysts in one-pot chemoenzymatic cascade reactions was overcome, resulting in improved activity and lower reaction temperature.
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Chemistry, Physical
Sergey P. Verevkin, Irina Andreeva, Aleksey A. Pimerzin
Summary: This study measured the absolute vapor pressures of three amino-alcohols using the transpiration method, and evaluated a consistent set of standard molar enthalpies of vaporization for eighteen amino-alcohols through empirical and structure-property correlations. The correlation between vaporization enthalpies and normal boiling temperatures was established, with vaporization enthalpies of amino-alcohols following group-additivity rules. The averaged values of vaporization enthalpies were recommended as reliable benchmark properties for heat management in CO2 capture technologies.
JOURNAL OF MOLECULAR LIQUIDS
(2021)
Article
Chemistry, Organic
Dongping Cheng, Yinqiang Shen, Ziliang Wu, Xiaoliang Xu, Jizhong Yan
Summary: A novel oxidative coupling of hydrazones and 1,3-diarylpropenes mediated by DDQ was disclosed, leading to the selective generation of 1,2-dihydropyridazines or pyrazoles through subsequent cyclization under metal-free conditions. The mechanisms of the coupling and cyclization were proposed in the study.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Food Science & Technology
Michele Ciulla, Valentino Canale, Rafal Damian Wolicki, Vincenzo Ferrone, Giuseppe Carlucci, Antonella Fontana, Gabriella Siani, Nicola D'Alessandro, Pietro Di Profio
Summary: This paper compares extraction methods using subcritical solvents, dimethyl ether (sC-DME) and n-butane (sC-nB), and finds that sC-DME exhibits higher selectivity and better yield for caffeine. It also discusses technical implementations to optimize subcritical solvent usage and demonstrates that extraction processes based on sub-critical solvents are easy to operate and efficient, and can be easily automated.
EUROPEAN FOOD RESEARCH AND TECHNOLOGY
(2023)
Article
Environmental Sciences
Fabio Girardi, Andrea Mascitti, Nicola D'Alessandro, Lucia Tonucci, Giuseppe Augusto Marzo, Romolo Remetti
Summary: This study aims to investigate the impact of the Fenton reaction, an oxidative treatment, on the biochemical methane potential of solid residues from olive oil production. The experiment reveals that the Fenton treatment improves the speed of methane production, reduces the bacteriostatic effect of phenols, decreases the H2S content in the produced biogas, and enhances methane production in the first four weeks of the test.
WASTE AND BIOMASS VALORIZATION
(2023)
Article
Chemistry, Applied
Philipp Petermeier, Christoph Kohlfuerst, Ana Torvisco, Roland C. C. Fischer, Alejandro Mata, Doris Dallinger, C. Oliver Kappe, Joerg H. H. Schrittwieser, Wolfgang Kroutil
Summary: Substituted piperidine rings are efficiently prepared with multiple stereocentres using multi-enzymatic and chemo-enzymatic methods from achiral diketoester precursors. Highly enantioselective transamination and diastereoselective reduction processes enable the synthesis of optically pure piperidines. This approach offers a more streamlined and efficient route for the synthesis of trisubstituted piperidines with potential applications in drug discovery.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
P. Petermeier, C. Kohlfuerst, A. Torvisco, R. C. Fischer, A. Mata, D. Dallinger, C. O. Kappe, J. H. Schrittwieser, W. Kroutil
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Mathias Pickl, Markus Ebner, Samantha Gittings, Pere Clapes, Wolfgang Kroutil
Summary: Although optical pure amino alcohols are highly demanded, their synthesis remains challenging due to the requirement of elaborate protection strategies. This study presents a multi-enzymatic methodology that allows the synthesis of enantioenriched 1,3-amino alcohols from commodity chemicals. By utilizing a Type I aldolase and enzymatic transamination, both diastereomers of the 1,3-amino alcohol motif were accessible, resulting in the desired amino alcohols with high enantioselectivity.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Xiaomin Xu, Jacob M. A. van Hengst, Yejia Mao, Mireia Martinez, Sergi Roda, Martin Floor, Victor Guallar, Caroline E. Paul, Miguel Alcalde, Frank Hollmann
Summary: A peroxygenase-catalysed hydroxylation of organosilanes has been reported, demonstrating efficient conversion of various silane starting materials and high catalyst performance. Molecular modelling of the enzyme-substrate interaction provides a basis for understanding the selectivity of AaeUPO.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Yinqi Wu, Caroline E. Paul, Thomas Hilberath, Ewald P. J. Jongkind, Wuyuan Zhang, Miguel Alcalde, Frank Hollmann
Summary: The utilization of fatty acids can be expanded by adding new functionalities to the hydrocarbon part. In this study, a peroxygenase mutant AaeUPO-Fett is demonstrated to selectively oxyfunctionalize fatty acids, leading to the production of ?-1 hydroxy fatty acid (esters). These hydroxy fatty acid (esters) can be further transformed into lactones, alcohols, esters, and amines through multi-enzyme cascades, providing new pathways for fatty acid valorisation.
Article
Chemistry, Physical
Chiara Domestici, Yinqi Wu, Thomas Hilberath, Miguel Alcalde, Frank Hollmann, Alceo Macchioni
Summary: Unspecific peroxygenases (UPOs) are promising biocatalysts for oxyfunctionalisation reactions, owing to their simplicity of handling, stability, and robustness. In this study, an organometallic complex [Cp*Ir(pica)NO3] was successfully used to efficiently regenerate FMNH2 from FMN, driven by NaHCOO, and then spontaneously react with O-2 to produce H2O2. The hybrid catalytic tandem of 1 and rAaeUPO PaDa-I showed excellent performances in hydroxylation, epoxidation, and sulfoxidation reactions.
Article
Agriculture, Multidisciplinary
Bin Wu, Shiyu Wang, Yunjian Ma, Shuguang Yuan, Frank Hollmann, Yonghua Wang
Summary: Alcohol oxidases catalyze the oxidation of alcohols to carbonyl products, with only H2O2 as the byproduct. To broaden their applicability, researchers performed enzyme engineering on a methanol oxidase, extending its substrate preference to a broad range of benzylic alcohols. A mutant with four substitutions exhibited improved catalytic activity, making it promising for use in the food industry.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2023)
Article
Multidisciplinary Sciences
Shun Zhang, Ruizhi Wu, Feng Zhong, Xiaochun Ma, Xiang Wang, Qiang Wu
Summary: The strength of bcc-structured Mg-Li alloy is improved by alloying Zn, with compressive yield strength reaching over 300 MPa due to semi-coherent B2 nanoparticles in cast state Mg-13Li-9Zn alloy. The compressive yield strength immediately increases to 400 MPa in as-quenched state Mg-13Li-15Zn (LZ1315) alloy, thanks to solid solution strengthening of Zn and the spinodal zone. Additionally, as-quenched LZ1315 alloy exhibits natural aging strengthening behavior, with yield strength up to 495 MPa due to precipitation of B2 nanoparticles.
FUNDAMENTAL RESEARCH
(2023)
Article
Chemistry, Physical
Chang Hyun Kim, Jinhyun Kim, Frank Hollmann, Chan Beum Park
Summary: Solar-driven N2 fixation provides a green alternative to the energy-intensive Haber-Bosch process, but the effect of oxidation reaction on N2 reduction has not been investigated in N2-reducing photo-electrochemical (PEC) studies. In this study, a bias-free PEC platform for N2 reduction and H2O oxidation was developed, and valuable chemicals were simultaneously synthesized on both electrodes using N2, H2O, and sunlight. This work represents the first example of a PEC NRR platform coupled with H2O oxidation and H2O2-dependent oxygenation for unbiased chemical synthesis.
APPLIED CATALYSIS B-ENVIRONMENTAL
(2023)
Article
Chemistry, Multidisciplinary
Christopher Grimm, Simona Pompei, Kristina Egger, Michael Fuchs, Wolfgang Kroutil
Summary: Lignin-derived aryl methyl ethers have potential as carbon sources in chemistry. An alternative method for their demethylation is through cobalamin-dependent enzymes, which require a methyltransferase and a carrier protein. Fusion proteins, connecting the methyltransferase with the corrinoid-binding protein, showed better performance than separate proteins, enabling a simpler protocol for demethylation. The fusion enzyme has promising applications in diversifying natural products and valorizing lignin.
Article
Chemistry, Physical
Willem B. Breukelaar, Nakia Polidori, Amit Singh, Bastian Daniel, Silvia M. Glueck, Karl Gruber, Wolfgang Kroutil
Summary: The biocatalytic reduction of oxime to amine has been observed in ene-reductases transforming alpha-oximo beta-keto esters. Through structural analysis, molecular dynamics simulations, biocatalytic cascades, and investigation of possible intermediates, it has been determined that the reaction proceeds via an imine intermediate and not through a hydroxylamine intermediate. A non-canonical tyrosine residue in ene-reductase OPR3 was found to play a role in protonating the hydroxyl group of the oxime in the first reduction step.
Article
Chemistry, Multidisciplinary
Emmanuel Cigan, Jakob Pletz, Sarah A. Berger, Bettina Hierzberger, Michael Grilec-Zlamal, Alexander Steiner, Isabel Oroz-Guinea, Wolfgang Kroutil
Summary: This study demonstrates an efficient access to the morphinan scaffold using a combination of organic synthesis and enzymatic reactions. The synthesis of a medicinally important compound class, promorphinans, was achieved by minimizing protecting group techniques and utilizing biocatalysis.
Article
Chemistry, Multidisciplinary
Xuemei Liu, Chaonan Cui, Shuoshuo Wei, Jinyu Han, Xinli Zhu, Qingfeng Ge, Hua Wang
Summary: This study presents a new strategy for designing efficient photocatalysts that can convert CO2 into hydrocarbons by utilizing synergistic catalytic sites. The findings provide a solution for the selective photocatalytic reduction of CO2 to CH4.
Article
Chemistry, Multidisciplinary
Chengxian Hu, Dan Wang, Lu Wang, Ying Fu, Zhengyin Du
Summary: A novel one-pot, three-component reaction conducted under electrochemical conditions was studied. The reaction involved 2-aminothiophenols, aldehydes, and malononitrile, using TBABF4 as an electrolyte and CuI as a catalyst. The proposed reaction mechanism suggested that CuI served as an electron relay. This method offers simplified operation, high atom economy, and mild reaction conditions.
Article
Chemistry, Multidisciplinary
Zhi Yang, Yu Chen, Linxi Wan, Yuxiao Li, Dan Chen, Jianlin Tao, Pei Tang, Fen-Er Chen
Summary: A highly enantioselective method for the complete hydrogenation of pyrimidinium salts using Ir/(S,S)-f-Binaphane complex as the catalyst was developed. This method provides easy access to fully saturated chiral hexahydropyrimidines, which are prevalent in many bioactive molecules. The reactions exhibit high yields and enantioselectivities under mild reaction conditions without additives. Successful application of this methodology in a continuous flow fashion further extends its practical utility.
Article
Chemistry, Multidisciplinary
Tina Jeoh, Jennifer Danger Nill, Wujun Zhao, Sankar Raju Narayanasamy, Liang Chen, Hoi-Ying N. Holman
Summary: In this study, the enzymatic hydrolysis of cellulose was investigated using real-time infrared spectromicroscopy. The spatial heterogeneity of cellulose was found to impact the hydrolysis kinetics. Hydration affected cellulose ordering, and Cel7A preferentially removed less extensively hydrogen bonded cellulose.
Article
Chemistry, Multidisciplinary
Tiphaine Richard, Walid Abdallah, Xavier Trivelli, Mathieu Sauthier, Clement Dumont
Summary: An effective method of grafting functionalities onto lignin based on glycerol carbonate has been developed using an efficient nickel-catalysed telomerisation reaction. This method allows lignin to have new reactive functions and reduces the glass transition temperatures of modified lignins, thereby expanding the application range of lignin-based resins.
Article
Chemistry, Multidisciplinary
Jing Qi, Xiyan Wang, Gan Wang, Srinivas Reddy Dubbaka, Patrick ONeill, Hwee Ting Ang, Jie Wu
Summary: This study presents a green and environmentally friendly approach for the synthesis of imides using electrocatalytic oxidation with H2O as the oxygen source. The method eliminates the need for toxic or expensive oxidants and achieves high yields under mild reaction conditions. It shows broad substrate compatibility and potential for industrial applications.
Article
Chemistry, Multidisciplinary
Babasaheb Sopan Gore, Lin-Wei Pan, Jun-Hao Lin, Yi-Chi Luo, Jeh-Jeng Wang
Summary: Here, we report a visible light-promoted intramolecular radical cascade reaction for the construction of fluorenol and naphthalene-fused cyclopropyl carbaldehyde derivatives. This method offers mild reaction conditions, a broad substrate scope, excellent step efficiency, and scalability, without the need for external chemical oxidants. The novelty of this protocol was demonstrated by synthesizing chrysene analogs and performing late-stage functionalizations.
Article
Chemistry, Multidisciplinary
Juho Antti Sirvio, Idamaria Romakkaniemi, Juha Ahola, Svitlana Filonenko, Juha P. Heiskanen, Ari Ammala
Summary: This article discusses the method of using supramolecular interaction between an aromatic hydrogen bond donor and lignin to achieve rapid delignification of softwood at low temperatures.
Article
Chemistry, Multidisciplinary
Yunyan Meng, Chunxiang Pan, Na Liu, Hongjiang Li, Zixiu Liu, Yao Deng, Zixiang Wei, Jianbin Xu, Baomin Fan
Summary: A novel visible light-driven synthesis method for 2,3-diamines has been developed, which has mild conditions, avoids the use of metal reagents, and can synthesize diamines and diols in one pot.
Article
Chemistry, Multidisciplinary
Mingqing Huang, Haiyang Huang, Mengyao You, Xinxin Zhang, Longgen Sun, Chao Chen, Zhichao Mei, Ruchun Yang, Qiang Xiao
Summary: A direct air-oxidized strategy for the synthesis of benzo[b]phosphole oxides was developed in this study. Arylphosphine oxides were transformed into phosphinoyl radicals, which were further combined with various alkynes to achieve the desired products. DFT calculations revealed the mechanism of phosphinoyl radical formation.
Article
Chemistry, Multidisciplinary
Anwei Wang, Jiayin Huang, Chunsheng Zhao, Yu Fan, Junfeng Qian, Qun Chen, Mingyang He, Weiyou Zhou
Summary: This study demonstrates an innovative strategy for the aerobic oxidation of C(sp(3))-H bonds using gamma-valerolactone. By optimizing the reaction conditions and utilizing specific catalysts, efficient oxidation of C(sp(3))-H bonds is achieved with good chemoselectivity in certain cases.
Article
Chemistry, Multidisciplinary
Shun Li, Likai Tong, Zhijian Peng, Bo Zhang, Xiuli Fu
Summary: Sulfide compounds show promise as electrocatalysts for water splitting, but their performance is limited by factors such as limited active sites and hindered substance transport. This study successfully prepared a high-entropy sulfide (ZnCoMnFeAlMg)(9)S-8, which reduced grain size and increased specific surface area, enabling the realization of a dual-functional catalyst with multiple catalytic sites. High entropy also modulated the electronic properties of sulfides, reducing the potential energy barrier for hydrolysis. This research introduces a new approach for functionalizing high entropy nanomaterials and improves the performance of water splitting catalysts.