Article
Chemistry, Organic
Ruslan A. Kovalevsky, Maxim Smirnov, Alexander S. Kucherenko, Kseniya A. Bykova, Elizaveta Shikina, Sergei G. Zlotin
Summary: In this study, 2-nitroallylic carbonates were used for the first time as promising biselectrophilic C3 synthons. They reacted with kojic acid derivatives in a bifunctional squaramide catalyzed asymmetric domino reaction, yielding nitro compounds that contain two hydroxypyranone units. The reaction products undergo noncatalytic epimerization at the carbon atom next to the nitro group. A plausible mechanism of the epimerization based on reversible formation of intermediate aci-nitro compound is proposed. The double addition products were transformed into configurationally stable acetates and chiral nitro glutarates, which are promising precursors for chiral amino glutaric acid derivatives.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Ahlem Meziadi, Navid Zuberi, Hendrick W. de Haan, Marc A. Gauthier
Summary: This study reveals that the inefficiency of bioconjugation reactions, such as protein PEGylation, is caused by the excluded volume effect (EVE) between methoxy poly(ethylene glycol) (mPEG) and proteins. The researchers found that this EVE leads to the self-assembly of proteins and reactive mPEG into separate protein-rich and mPEG-rich domains. By adding unreactive low-molecular weight mPEG as a co-solvent, the association between the larger protein and reactive mPEG can be promoted, resulting in improved reaction efficiency.
Article
Chemistry, Multidisciplinary
Morgan D. McSweeney, Limei Shen, Alexander C. DeWalle, Jordan B. Joiner, Elizabeth C. Ciociola, Dharmendra Raghuwanshi, Matthew S. Macauley, Samuel K. Lai
Summary: This study explored the effectiveness of prophylaxis with free PEG or tolerogenic PEGylated liposomes as a strategy to reduce the amount of APA induced by subsequently administered PEGylated liposomes. The results showed that a single administration of free PEG alone was capable of markedly reducing the APA response to PEG-liposomes for up to 2 months, which was comparable to, and often exceeded, interventions with different tolerogenic PEG-liposomes. These findings support further research on free PEG prophylaxis as a potential strategy to mitigate the APA response to sensitizing PEGylated therapeutics.
JOURNAL OF CONTROLLED RELEASE
(2021)
Article
Chemistry, Organic
Prasenjit Gayen, Prasanta Ghorai
Summary: A highly chemoselective 1,2-addition of thiols with 2-isothiocyanatochalcones followed by an enantioselective intramolecular thia-Michael addition cascade has been developed for the synthesis of enantioenriched [1,3]-benzothiazine derivatives. The squaramide catalyst derived from cinchona provides excellent yield and enantioselectivity with a wide range of substrates. Furthermore, this strategy can be extended to access enantioenriched organophosphorus-substituted [1,3]-benzothazines using diphenylphosphine oxide nucleophile.
Article
Chemistry, Multidisciplinary
Zhao Han, Jiaping Jin, Alemayehu Gashaw Woldegiorgis, Xufeng Lin
Summary: An efficient organocatalytic method has been developed for the synthesis of enantioenriched triflouromethylated indolin-2-ones bearing adjacent tertiary chiral centers. The use of a newly developed chiral spirobiindane-derived squaramide catalyst is essential in achieving high diastereo- and enantioselectivities.
Article
Biochemistry & Molecular Biology
Asim Mushtaq, Li Li, A. Anitha, Lisbeth Grondahl
Summary: This study synthesized methoxy polyethyleneglycol grafted chitosan (mPEG-CHI) using carbodiimide-mediated coupling and evaluated the effect of reaction conditions on the degree of substitution and PEGylation yield. The optimized conditions resulted in a high DS and PEGylation yield, making the product suitable for medical applications. The cytotoxicity of mPEG-CHI was also assessed and found to be non-toxic against breast cancer cell lines.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2022)
Article
Chemistry, Multidisciplinary
Xiu-Ning Hu, Dong-Ping Wu, Ye-Peng Xu, Pei-Qiang Huang
Summary: The first organocatalytic asymmetric synthesis of an advanced intermediate of (+)-sarain A was achieved by combining organocatalytic asymmetric Michael addition reaction and a nitrogen-to-carbon chirality transfer. This method allows for the construction of three chiral centers and chemoselective reduction of a key lactam intermediate, providing a tricyclic intermediate with all necessary functionalities for further elaboration into (+)-sarain A.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Taro Shimizu, Mizuki Awata, Amr S. Abu Lila, Chihiro Yoshioka, Yoshino Kawaguchi, Hidenori Ando, Yu Ishima, Tatsuhiro Ishida
Summary: In this study, we developed a delivery system using hydroxy PEG-modified liposomes (HO-PEG-Lip) that efficiently activated the complement system, facilitated the association with MZ-B cells, and significantly enhanced antigen delivery in vivo. The manipulation of HO-PEG density at 2 mol% in total lipids led to a successful induction of OVA-specific IgG response after a single intravenous injection. This new delivery technique may provide a simple and effective way to deliver antigens to MZ-B cells, inducing a significant humoral immune response.
JOURNAL OF CONTROLLED RELEASE
(2021)
Review
Chemistry, Multidisciplinary
Tapaswini Das, Seetaram Mohapatra, Nilima P. Mishra, Sabita Nayak, Bishnu P. Raiguru
Summary: The recent advancements in organocatalytic Michael addition reactions to alpha, beta-unsaturated nitroolefins have been discussed, highlighting the rapid innovations made possible by newly developed chiral organocatalysts and the essential role of nitroolefins as well-known Michael acceptors providing structurally necessary nitro-functionalized frameworks.
Article
Materials Science, Biomaterials
Kai Sugiura, Toshiki Sawada, Yuuki Hata, Hiroshi Tanaka, Takeshi Serizawa
Summary: This study demonstrates a simple method for distinguishing anti-PEG antibodies using antibiofouling cello-oligosaccharide assemblies tethering specific one-terminal methoxy oligo(ethylene glycol) ligands. The method allows for quantitative detection of the antibodies, even in the presence of serum.
JOURNAL OF MATERIALS CHEMISTRY B
(2023)
Review
Chemistry, Organic
Arabinda Chandra Nath, Gongutri Borah
Summary: Green solvent is an important topic in modern chemistry. In recent years, significant progress has been made in addressing the environmental and health impacts of solvents through sustainable synthesis. This review article examines various synthetic methodologies and applications of sustainable solvents, as well as their mechanisms and utility in chemical reactions.
CURRENT ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Fushuai Li, Zhihong Yang, Yanyan Yang, Qiuhong Huang, Xuling Chen, Pengfei Li, Mingxin Dong, Wenjun Li
Summary: A chiral phosphorus acid catalyzed enantioselective 1,4-conjugate addition of arylamines to in situ formed 7-methylene-7H-indoles from 7-indolylmethanols has been successfully developed for the first time without the use of additives. The catalytic protocol enables the formation of 1,4-adducts with a nitrogen-containing tertiary carbon stereocenter in moderate to high yields and good enantioselectivity under mild reaction conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
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)
Article
Environmental Sciences
S. P. Keerthana, R. Yuvakkumar, P. Senthil Kumar, G. Ravi, S. Hong, Dhayalan Velauthapillai
Summary: In this study, polyethylene glycol-assisted antimony tungstate nanorod photocatalysts were prepared via a hydrothermal route. The properties of the catalysts were investigated, and it was found that the 10 ml PEG-assisted sample exhibited a narrow bandgap and nanorod growth without agglomeration. Fourier transform infrared spectroscopy and Raman spectroscopy confirmed the composition and vibrational modes of the samples. Furthermore, the prepared 10 ml PEG-Sb2WO6 photocatalyst showed high efficiency and stability in degrading toxic pollutants in wastewater, making it a promising candidate for water treatment applications.
Article
Chemistry, Organic
Douglas B. Paixao, Eduardo G. O. Soares, Helena D. Salles, Caren D. G. Silva, Daniel S. Rampon, Paulo H. Schneider
Summary: This work introduces the use of rongalite in PEG-400 as a reductive system for the synthesis of chalcogenophenes from 1,3-butadiynes. The system provides nucleophilic chalcogen species that can add selectively to the triple bond, allowing the synthesis of a wide range of chalcogenophenes. The method is environmentally friendly, cost-effective, and allows for the reuse of PEG-400 for multiple reactions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Review
Chemistry, Organic
Natalia M. Moreira, Jhonathan R. N. dos Santos, Arlene G. Correa
Summary: Quinazoline derivatives have garnered attention in synthetic and medicinal chemistry due to their wide range of biological activities and potential pharmacological applications. Recent research has focused on greener methods for synthesizing these compounds.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Organic
Guilherme A. M. Jardim, Juliana A. Dantas, Amanda A. Barboza, Marcio W. Paixao, Marco A. B. Ferreira
Summary: Visible-light-induced palladium-mediated reactions have shown great potential in organic synthesis and can achieve new and unique reactivities by generating versatile Pd-radical hybrid species. This review provides an overview of recent advances in the combination of Pd-based photocatalytic manifolds and radical generation in the functionalization of important motifs in synthetic chemistry.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Wanderson C. C. de Souza, Rafaely N. N. Lima, Iva S. S. de Jesus, Jose Tiago M. Correia, Marcio W. Paixao
Summary: A deaminative alkyl radical cascade cyclization of 1,7-dienes under visible-light photocatalysis is reported. This method enables the synthesis of a family of benzoazepinones (benzazepinones) and can be carried out under mild reaction conditions, providing a broad substrate scope with excellent functional group tolerance and good yields. This protocol has also been extended to 1,7-enynes, resulting in a representative collection of cyclopentaquinolinones.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Kimberly Benedetti Vega, Jose Antonio Campos Delgado, Lucas V. B. L. Pugnal, Burkhard Koenig, Jose Tiago Menezes Correia, Marcio Weber Paixao
Summary: In this study, a strategy for the precise installation of sulfones and carboxylic acids onto styrenes using sodium sulfinates and CO2 as coupling partners was described. The protocol allowed for the preparation of carboxy-sulfonylated compounds with high yields and broad functional group tolerance. Additionally, a one-pot photocatalytic carboxy-sulfonylation-elimination strategy was developed for the synthesis of alpha-aryl-acrylates by taking advantage of the leaving group ability of the sulfone moiety.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Biochemistry & Molecular Biology
Everton Machado da Silva, Herika Danielle Almeida Vidal, Marcelo Augusto Pereira Januario, Arlene Goncalves Correa
Summary: BINOL derivatives are significant in terms of their biological activities and functionality as chiral ligands and catalysts, hence attracting considerable interest in their asymmetric synthesis. This paper provides an overview of the most efficient methods for obtaining chiral BINOLs, with emphasis on the utilization of metal complexes and organocatalysts, as well as kinetic resolution. Further derivatizations of BINOLs are also addressed.
Article
Biochemistry & Molecular Biology
Gustavo Cabrera-Barjas, Romel Jimenez, Romina Romero, Oscar Valdes, Aleksandra Nesic, Ruber Hernandez-Garcia, Andronico Neira, Serguei Alejandro-Martin, Alexander F. de la Torre
Summary: In this study, chitin, a biobased polymer, was used as a precursor to obtain phosphorylated derivatives. The influence of different degrees of phosphorylation in chitin on pyrolysis pattern was investigated. Through FTIR, SEM, and Py-GC/MS analysis, the thermal degradation and evolved gases during chitin degradation and its derivatives were measured. The results showed that phosphorylation of chitin decreased its thermal stability and significantly changed the pyrolysis pattern, leading to the production of long-chain hydrocarbons.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2023)
Article
Chemistry, Organic
Nataïlia M. Moreira, Ingrid T. de Miranda, Jhonathan R. N. dos Santos, Till Opatz, Glaucius Oliva, Rafael V. C. Guido, Arlene G. Correa
Summary: Reactions involving C(sp(3))-H bonds of azaarenes have been extensively studied for their ability to directly functionalize these N-heterocycles without harsh conditions. In this study, α-substituted β-nitrostyrenes catalyzed by inexpensive copper acetate were employed to functionalize 4-methylquinazolines and 1-benzylisoquinolines. Under optimized conditions, 21 pyrrolo[1,2-c]quinazolines, an imidazo[1,2-c]quinazoline, and 4 pyrrolo[2,1-a]isoquinolines were obtained in moderate to good yields. Furthermore, the biological activity of the pyrrolo[1,2-c]quinazolines against Plasmodium falciparum was evaluated and promising results were obtained.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Shahzaib Akhter, Odette Concepcion, Alexander Fernandez de la Torre, Akbar Ali, Abdul Rauf Raza, Rida Eman, Muhammad Khalid, Muhammad Fayyaz ur Rehman, Muhammad Safwan Akram, Hayssam M. Ali
Summary: Peptoids are designed to mimic peptides with increased stability and activity. Quinoline-based peptoids were synthesized and characterized, and their electronic properties were studied using computational analysis. In silico methods were used to predict the biological activities of the peptoids, and in vitro experiments confirmed their anticholinesterase activity. Overall, this research provides valuable insights into the design and evaluation of peptoids for various biological applications.
ARABIAN JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Marcelo Augusto Pereira Januario, Demetrius P. de Souza, Julio Zukerman-Schpector, Arlene G. Correa
Summary: Highly functionalized indole derivatives were synthesized via Rh(III)-catalyzed C-2 alkylation with nitroolefins. A total of 23 examples were prepared under optimized conditions with yields ranging from 39% to 80%. Furthermore, the nitro compounds were reduced and subjected to the Ugi four-component reaction, resulting in a series of new indole-peptidomimetics with moderate to good overall yields.
Review
Chemistry, Physical
Lorena S. R. Martelli, Ingrid V. V. Machado, Jhonathan R. N. dos Santos, Arlene G. G. Correa
Summary: Efficient synthetic methods that avoid the use of hazardous reagents and solvents have become crucial in organic synthesis. Organocatalysis is a powerful tool for building chemical bonds, but most examples still use toxic volatile organic solvents. This review discusses the use of bio-based solvents in asymmetric organocatalytic methods and their proposed mechanisms.
Article
Chemistry, Multidisciplinary
Muhammad Saeed Ahmad, Abu Bakar Siddique, Muhammad Khalid, Akbar Ali, Muhammad Ashraf Shaheen, Muhammad Nawaz Tahir, Muhammad Imran, Ahmad Irfan, Muhammad Usman Khan, Marcio Weber Paixao
Summary: In this study, a one-pot synthesis of tetra-substituted imidazole was reported, and a series of metal complexes were obtained by reacting the synthesized imidazole with salts of 1(st) row transition metals. The synthesized compounds were characterized using spectroscopic and analytical techniques, and their antioxidant and antimicrobial activities were evaluated. The results showed that the metal complexes exhibited stronger antimicrobial activity compared to the ligand, and the ligand had better antioxidant activity than the metal complexes. Computational studies revealed a clear intra-molecular charge transfer in the ligand and its metal complexes.
Article
Chemistry, Organic
Lorena S. R. Martelli, Otavio A. M. da Silva, Julio Zukerman-Schpector, Arlene G. Correa
Summary: This work presents a simple one-pot diastereoselective synthesis of new gamma-lactams from ketoaziridines via the Horner-Wadsworth-Emmons reaction, followed by intramolecular ester-aziridine cyclization and its in situ opening. The method provides new gamma-lactams in moderate to good yields, and initial efforts towards an enantioselective version are reported.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Bianca T. Matsuo, Pedro H. R. Oliveira, Emanuele F. Pissinati, Kimberly B. Vega, Iva S. de Jesus, Jose Tiago M. Correia, Marcio Paixao
Summary: This review summarizes the latest advances in the preparation of amide-containing compounds using carbamoyl radicals. The application of photoinduced protocols provides a range of structurally relevant derivatives. The study also discusses a recent approach using photolytic C-S cleavage of dithiocarbamate-carbamoyl intermediates.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Odette Concepcion, Francisco J. Penaloza, Jhon Jairo Lopez, Gustavo Cabrera-Barjas, Claudio A. Jimenez, Marcio W. Paixao, Alexander F. de la Torre
Summary: This study presents a simple method for synthesizing N-alkylated peptides and depsipeptides containing olefins, which can be achieved through sequential one-pot protocol of multicomponent reaction and oxidative elimination. The regioselective construction of alpha,beta-dehydrobutyrine and alpha,beta-dehydro-homophenylalanine was possible using Ugi four-component reaction, while the Passerini three-component reaction produced beta-enamide preferably.
NEW JOURNAL OF CHEMISTRY
(2022)
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.
