Article
Chemistry, Multidisciplinary
Hongkun Xu, Xuan Qin, Yaping Zhang, Chuan Wan, Rui Wang, Zhanfeng Hou, Xiaofeng Ding, Hailing Chen, Ziyuan Zhou, Yang Li, Chenshan Lian, Feng Yin, Zigang Li
Summary: The modification and functionalization of peptides play a crucial role in biotechnology and drug development. A highly reactive Michael-type warhead is reported here for the covalent modification of cysteine on peptides and proteins. By incorporating a vinyl group onto a methionine residue, the resulting vinyl sulfonium can be efficiently nucleophilically added by a suitable cysteine residue, leading to the formation of cyclized peptides. This peptide cyclization strategy demonstrates improved cell penetration and stability. Furthermore, a peptide ligand containing vinyl sulfonium can covalently bind to cysteine in the target protein, indicating the potential of vinyl sulfonium as a novel warhead for developing covalent peptide inhibitors.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Physical
Lei Wang, Wei Song, Binju Wang, Yan Zhang, Xin Xu, Jing Wu, Cong Gao, Jia Liu, Xiulai Chen, Jinghua Chen, Liming Liu
Summary: A one-pot enzymatic-chemical cascade route was developed to synthesize 2-Hydroxyacetophenone (2-HAP) with a final yield of 92.7%. The introduction of stereospecific carbonyl reductases allowed for further transformation of 2-HAP into (S)- and (R)-1-phenyl-1,2-ethanediol. This method shows potential for synthesizing other valuable chemicals by cascading spontaneous chemical and enzymatic reactions.
Article
Chemistry, Applied
Jen-Yu Kuan, I-Ting Chen, Hsuan Lin, Jeng-Liang Han
Summary: We have developed a substrate-dependent, regio- and stereocontrolled diversity-oriented organocatalytic vinylogous Michael addition/cyclization cascade of 2-alkylidene indane-1,3-diones with enals, using secondary amines as the catalyst. This method allows for the selective synthesis of spiroindane-1,3-diones, tetrahydrofluoren-9-one derivatives, and benzofused oxabicyclo[3.3.1]nonanes. Plausible catalytic pathways have been proposed, and DFT calculations have clarified the mechanisms involved.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Applied
Yong-Xing Song, Da-Ming Du
Summary: The aza-Michael addition cascade reaction is an important synthetic method for constructing functionalized C-N bonds, widely used in the synthesis of chiral drugs, intermediates, and natural products. This review highlights recent developments in asymmetric synthesis, including various types of aza-Michael addition triggered cascade reactions, reaction mechanisms, and derivatization experiments.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Biochemistry & Molecular Biology
Guishun Bai, Yang Yang, Xingyue Wang, Jiamin Wu, Hong Wang, Xinyi Ye, Xiaoze Bao
Summary: A DBU-promoted cascade reaction for the synthesis of polysubstituted arenes was reported, featuring mild reaction conditions, wide substrate scope, and high yield. The enantioselective version of this reaction was explored to produce chiral biaryl atropisomers.
Review
Chemistry, Multidisciplinary
Cheng Niu, Da-Ming Du
Summary: This review highlights the recent advancements in sulfa-Michael addition-triggered cascade reactions for the stereoselective synthesis of sulfur-containing compounds. It discusses various types of reactions, including sulfa-Michael/aldol, sulfa-Michael/Henry, sulfa-Michael/Michael, sulfa-Michael/Mannich and some sulfa-Michael triggered multi-step processes. The review also introduces reaction mechanisms and derivatization experiments.
Article
Chemistry, Organic
Manman Sun, Jing Gui, Rong Zhong, Haijian Wu, Saimei Liu, Jinshan Li, Jianguo Yang, Zhiming Wang
Summary: A TfOH-catalyzed direct Michael addition and cascade cyclization reactions of azadienes with unactivated ketones have been developed, providing a divergent approach to 2,3-disubstituted benzofurans and benzofuro[3,2-b]pyridines. This method utilizes the weak nucleophilicity of unactivated ketones and controls the catalyst acidity as a key parameter. The use of commercial ketones and mild reaction conditions also offer synthetic and environmentally benign advantages.
Article
Chemistry, Physical
Viktoria Kozma, Gyorgy Szollosi
Summary: In this study, asymmetric Michael additions of 1,3-dicarbonyl compounds to N-substituted maleimides were carried out using primary amine-(thio)phosphoramide bifunctional chiral organocatalysts derived from optically pure C-2-symmetric 1,2-diamines. The results show that the addition of ethyl 2-fluoroacetoacetate using the thiophosphoramide catalyst derived from 1,2-diphenylethane-1,2-diamine afforded succinimides substituted with fluorine bearing quaternary carbon in high yields, good diastereomeric ratios and excellent enantiomeric excesses. The bulkiness of the N-substituent of the maleimide ring influenced mostly the conversions. Additionally, the thiophosphoramide catalyst was found efficient in the addition of ethyl 2-fluoroacetoacetate to beta-nitrostyrenes.
MOLECULAR CATALYSIS
(2022)
Article
Multidisciplinary Sciences
Firouz Matloubi Moghaddam, Vahid Saberi, Ashkan Karimi
Summary: The first diastereoselective synthesis of spirothiooxindoles was achieved via Michael reaction without any catalyst. The method is scalable, environmentally friendly, and facilitates easy purification without column chromatography. Molecular docking studies suggest that the obtained cis-spirooxindoles exhibit higher binding affinities for the OPRT domain of LdUMPS, indicating potential for the development of new compounds for leishmaniasis treatment.
SCIENTIFIC REPORTS
(2021)
Article
Agricultural Engineering
Peiqian Zhang, Mei Cui, Renliang Huang, Wei Qi, Wim Thielemans, Zhimin He, Rongxin Su
Summary: This study investigated the mechanism of expansins and endoglucanase on cellulose using real-time monitoring technology. The addition of zinc ions was found to increase the adsorption rate and hydrolysis rate of both expansins and endoglucanase.
BIORESOURCE TECHNOLOGY
(2021)
Article
Environmental Sciences
Xing Zhu, Yi Tian, Bin He
Summary: Enzymatic modification has been used to reduce the cost and improve the efficiency of starch solid waste treatment. The modified enzymes have a specific temperature range where they can dissolve and react effectively. This method allows for efficient hydrolysis of the wastes and easy recovery and separation, leading to a significant reduction in treatment costs.
ENVIRONMENTAL RESEARCH
(2023)
Article
Chemistry, Multidisciplinary
Sakamuri Sarath Babu, A. Anagha Varma, Purushothaman Gopinath
Summary: We report a substrate-controlled cascade cyclization method for constructing functionalized heterocycles using photoredox catalysis under mild conditions. This versatile method has been successfully applied to a wide range of substrates and for the synthesis of functionalized etifoxine drug derivatives.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Tianyu Yang, Zhoubin Deng, Ke-Hu Wang, Pengfei Li, Yuyu Lv, Danfeng Huang, Yongwei Shang, Yingpeng Su, Yulai Hu
Summary: A highly efficient ZnBr2 promoted Michael addition/annulation cascade reaction of difluoromethyl-alpha,beta-ynones with beta-enamino derivatives has been developed, leading to the synthesis of a series of CHF2-substituted pyridines. These pyridines can be further converted into potentially biological active difluoromethylated 4-azafluorenes, providing a new strategy for the synthesis of bioactive molecules.
Article
Chemistry, Organic
Abhisek Midya, Laxman Devidas Khalse, Prasanta Ghorai
Summary: In this study, an amine-catalyzed reductive aldol-condensation followed by an intramolecular reductive Michael-addition cascade was demonstrated, using Hantzsch ester as a hydride source to a keto-bis-enone, leading to the synthesis of enantio- and diastereoselective benzannulated diquinanes with three consecutive stereocenters, including an all-carbon quaternary formyl stereocenter. Interestingly, changing the tether from an aliphatic to an aromatic moiety resulted in a change in reactivity, where an asymmetric aldol reaction, followed by an iminium/enamine isomerization and diastereoselective Michael addition reaction, resulted in the formation of a bis-benzannulated diquinane with vicinal congested quaternary chiral centers.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Polymer Science
Hao Fu, Linbo Gong, Shuling Gong
Summary: In this study, a self-dispersible, non-ionic waterborne comb-like polyester (NWCPE) was successfully synthesized by grafting an amino-terminated hydrophilic polyether to a series of linear polyesters using a facile and mild aza-Michael addition. The NWCPE dispersion showed excellent storage stability and hydrolysis resistance, and the cross-linked film exhibited good water resistance and mechanical properties.
Review
Biochemical Research Methods
Alexis Lossouarn, Pierre-Yves Renard, Cyrille Sabot
Summary: Kinetic target-guided synthesis (KTGS) is a promising tool for discovering biologically active compounds by covalently assembling potent ligands from a pool of reagents. However, the current limited number of biocompatible reactions may not meet the specificities of a wide range of biological targets, thus new reaction types are needed.
BIOCONJUGATE CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Elisabet Viayna, Nicolas Coquelle, Monika Cieslikiewicz-Bouet, Pedro Cisternas, Carolina A. Oliva, Elena Sanchez-Lopez, Miren Ettcheto, Manuela Bartolini, Angela De Simone, Mattia Ricchini, Marisa Rendina, Megane Pons, Omidreza Firuzi, Belen Perez, Luciano Saso, Vincenza Andrisano, Florian Nachon, Xavier Brazzolotto, Maria Luisa Garcia, Antoni Camins, Israel Silman, Ludovic Jean, Nibaldo C. Inestrosa, Jacques-Philippe Colletier, Pierre-Yves Renard, Diego Munoz-Torrero
Summary: By combining the scaffolds of the cholinesterase inhibitor huprine Y and the antioxidant capsaicin, compounds with nanomolar potencies towards AChE and BChE were created, demonstrating potential therapeutic effects for Alzheimer's disease.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Applied
Quentin Ibert, Madeleine Cauwel, Thomas Glachet, Tony Tite, Patricia Le Nahenec-Martel, Jean-Francois Lohier, Pierre-Yves Renard, Xavier Franck, Vincent Reboul, Cyrille Sabot
Summary: Broad scope one-pot diazirine synthesis strategies have been developed using two different oxidants depending on the nature of the starting material. The methods are operationally simple, and tolerant to most functional groups, providing diazirines with yields ranging from 20 to 99%.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Editorial Material
Biochemistry & Molecular Biology
Cyrille Sabot, Peter Kele
Article
Chemistry, Multidisciplinary
Walter Hofer, Emilia Oueis, Antoine Abou Fayad, Felix Deschner, Anastasia Andreas, Lais Pessanha de Carvalho, Stephan Huettel, Steffen Bernecker, Linda Paetzold, Bernd Morgenstern, Nestor Zaburannyi, Markus Bischoff, Marc Stadler, Jana Held, Jennifer Herrmann, Rolf Mueller
Summary: The rise of antimicrobial resistance poses a severe threat to public health. Chlorotonil, a new antibiotic targeting multidrug resistant pathogens, was found to have promising activities. However, its pharmaceutical properties needed improvement. By semisynthesis, derivatives with enhanced solubility were obtained, and their stability and activity were verified in vivo.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Medicinal
Ophelie Da Silva, Nicolas Probst, Christophe Landry, Anne-Sophie Hanak, Pierre Warnault, Caroline Coisne, Andre-Guilhem Calas, Fabien Gosselet, Charlotte Courageux, Anne-Julie Gastellier, Marilene Trancart, Rachid Baati, Marie-Pierre Dehouck, Ludovic Jean, Florian Nachon, Pierre-Yves Renard, Jose Dias
Summary: Recent events have highlighted the serious threat posed by organophosphorus nerve agents to civilian and military populations. This study proposes the use of glucoconjugated oximes without permanent charge as potential central nervous system reactivators, aiming to overcome the current limitations in therapy. The study evaluates the effectiveness of these compounds, their structural characteristics, and their permeability through the blood-brain barrier.
JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Alexis Lossouarn, Chloe Puteaux, Laetitia Bailly, Vincent Tognetti, Laurent Joubert, Pierre-Yves Renard, Cyrille Sabot
Summary: This study reports a protein-directed synthesis method for synthesizing carbonic anhydrase inhibitors and discovers unexpected photophysical properties. Fine-tuning of substituents on the coumarin moiety allows for bidirectional photochemical reactions, leading to the discovery of a new photoswitch moiety with fluorescence properties.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Environmental Sciences
Yolande Saab, Emilia Oueis, Stephanie Mehanna, Zahi Nakad, Rita Stephan, Rony S. Khnayzer
Summary: This study assessed the potential risks of phthalate esters (PAEs) in IV bags manufactured in Lebanon. Results showed that DEHP, the predominant phthalate found, exceeded safe limits in some samples, posing a particular risk to neonates. Therefore, restrictions should be imposed on the use of phthalates in medical IV bags.
Article
Chemistry, Multidisciplinary
Lena Keller, Emilia Oueis, Amninder Kaur, Nasim Safaei, Susanne H. Kirsch, Antonia P. Gunesch, Sibylle Haid, Ulfert Rand, Luka Cicin-Sain, Chengzhang Fu, Joachim Wink, Thomas Pietschmann, Rolf Mueller
Summary: A new strain of actinobacteria, Kibdelosporangium persicum sp. nov., collected from a hot desert in Iran, yielded a novel family of sesquarterpenoids (persicamidines A-E) with remarkable antiviral activity. Extensive NMR analysis revealed a hexacyclic terpenoid molecule with a modified sugar moiety on one side and a unique isourea moiety fused to the terpenoid structure. Persicamidines A-E exhibited potent activity against hCoV-229E and SARS-CoV-2 viruses in the nanomolar range, along with excellent selectivity indices, showing promise as potential drug candidates.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Organic
Kevin Renault, Pierre-Yves Renard, Cyrille Sabot
Summary: This review provides an overview of the synthesis of quinoxalin-2(1H)-ones and discusses their fluorescence properties and applications, including chemosensing and biosensing.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Steven Vertueux, Alexandre Haefele, Kathleen Solmont, Philippe Durand, Pierre-Yves Renard
Summary: A series of chemiluminescent cassettes based on adamantyl stabilized 1,2-dioxetanes linked to a fluorophore by a conjugated linker were synthesized in this study. The chemiluminescent decomposition and photoluminescence properties of their respective emissive species were investigated.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Maxime Boddaert, Pauline Bianchi, Diana V. Silva-Brenes, Ancuta Musina, Marc Winter, Philippe M. C. Roth, Pierre-Yves Renard, Julien Legros, Jean-Christophe M. Monbaliu
Summary: This study introduces a new, efficient, safe, and sustainable flow protocol using ozone to oxidatively neutralize sulfur-based chemical warfare agent simulants. The combination of computational research and experimental validation has successfully achieved rapid neutralization under flow conditions.
Article
Chemistry, Multidisciplinary
Sergui Mansour, Antonin Delaune, Maxime Manneveau, Baptiste Picard, Amelie Claudel, Cecile Vallieres, Lea Sigot, Pierre-Yves Renard, Julien Legros
Summary: This study found that the neutralisation of a simulant of the chemical warfare agent VX can be effectively carried out with lithium ethanolate in a nylon custom printed flow reactor. The formation of EtOLi and the neutralisation can be completed in a single operation. Additionally, the robustness and recyclability of the device were demonstrated.
Article
Chemistry, Multidisciplinary
Antonin Delaune, Sergui Mansour, Baptiste Picard, Philippe Carrasqueira, Isabelle Chataigner, Ludovic Jean, Pierre-Yves Renard, Jean-Christophe M. Monbaliu, Julien Legros
Summary: The oxidative neutralisation of sulfur-containing CWAs with Oxone in flow systems has been developed, and in order to achieve full selectivity towards harmless decomposition products, Oxone must be used in either solid or aqueous form.
Article
Chemistry, Multidisciplinary
Madeleine Cauwel, Clement Guillou, Kevin Renault, Damien Schapman, Magalie Benard, Ludovic Galas, Pascal Cosette, Pierre-Yves Renard, Cyrille Sabot
Summary: This study presents a novel photoaffinity probe based on quinoxalinone, which can covalently capture proteins and label them with fluorescence under visible blue LED irradiation (max wavelength 450 nm). This process allows monitoring applications without the need for washing.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
