Article
Chemistry, Applied
Subhasish Ray, Saurabh Singh, Ganesh Kumar, Gaurav Shukla, Maya Shankar Singh
Summary: A chemoselective route to thiazolines and thiazines has been developed via heterocyclization of viable alpha-N-hydroxyimino-beta-oxodithioesters with 2-chloroethylamine hydrochloride/3-chloropropylamine hydrochloride. This method does not require metals or additives and can proceed at temperatures ranging from 0 to 60 degrees Celsius. The overall transformation involves base mediated intramolecular cyclization followed by coupling with chloroalkyl amines, enabling the construction of thiazolines/thiazines in one-pot. This strategy expands the synthetic methods available for obtaining N,S-heterocycles.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Jiao-Mei Wang, Teng Chen, Chang-Sheng Yao, Kai Zhang
Summary: Herein, an NHC (N-heterocyclic carbene)-catalyzed radical coupling reaction between aldehydes and azobis(isobutyronitrile) (AIBN) has been developed, providing an efficient and convenient approach for the synthesis of fi-ketonitriles containing a quaternary carbon center (31 examples, up to >99% yield) utilizing commercially available substrates. This protocol features broad substrate scope, good functional group tolerance, and high efficiency under metal-free and mild reaction conditions.
Article
Chemistry, Organic
Debashish Mishra, Sauvik Kashyap, Prodeep Phukan
Summary: A cascade protocol for the synthesis of aminotetrazoles has been developed, achieving excellent yields and broad substrate scope without the use of any metals. The reaction proceeds via an isolable carbodiimide intermediate and intermolecular cyclization, providing 5-aminotetrazoles in a short reaction time.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Multidisciplinary Sciences
Xiaochen Wang, Rongxin Yang, Binbing Zhu, Yuxiu Liu, Hongjian Song, Jianyang Dong, Qingmin Wang
Summary: Here, the authors describe a multicatalytic method for the synthesis of beta, gamma-unsaturated ketones via allylic acylation of alkenes. The method combines N-heterocyclic carbene catalysis, hydrogen atom transfer catalysis, and photoredox catalysis for cross-coupling reactions. The method shows excellent site selectivity and could be used for the synthesis of diverse beta, gamma-unsaturated ketones using carboxylic acids and olefins as substrates.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Johannes E. Erchinger, Reece Hoogesteger, Ranjini Laskar, Subhabrata Dutta, Carla Huempel, Debanjan Rana, Constantin G. Daniliuc, Frank Glorius
Summary: This article presents a new synthetic method that utilizes a photosensitizer to react sulfur fluoride compounds with alkenes, resulting in protected beta-amino sulfonyl fluorides. This method can be used to synthesize peptido sulfonyl fluorides, beta-ammonium sulfonates, and beta-sultams relevant in medicinal chemistry.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Branislav Ferko, Michaela Marcekova, Katarina Rachel Detkova, Jana Dohanosova, Dusan Berkes, Pavol Jakubec
Summary: A new stereoselective denitrative cross-coupling reaction has been developed for the synthesis of functionalized styrenes. The reaction is visible-light induced and doesn't require catalyst at room temperature, showing broad scope and tolerance to multiple functional groups, providing an alternative to traditional metal-catalyzed cross-couplings.
Article
Chemistry, Applied
Mayuko Tsukahara, Muhammet Uyanik, Kazuaki Ishihara
Summary: Here, a direct method for synthesizing α-imidoketones and α-azolylketones through hypoiodite-catalyzed oxidative α-C-N coupling of ketones with imides and azoles, respectively, is reported. The presence of inorganic base additives, such as cesium carbonate, in the presence of 18-crown-6 as a phase transfer catalyst, is crucial in promoting high reactivity. Control experiments suggest that the basic additives not only facilitate high-turnover hypoiodite catalysis but also participate in the activation of coupling partners.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Yuan-Yuan Xu, Zhong-Hua Gao, Cao-Bo Li, Song Ye
Summary: The enantioselective alpha-oxidative coupling of enals with carboxylic acids was achieved by umpolung of an NHC-bound enolate with an iodine(III) reagent. The reaction produced alpha-acyloxyl-beta,gamma-unsaturated esters in good yields, with high regio- and enantioselectivities. The reaction involved the formation of an enol iodine(III) intermediate from the enolate with iodosobenzene, which changed the polarity of the enal's alpha-carbon from nucleophilic to electrophilic and facilitated the subsequent carboxylate addition.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Agriculture, Multidisciplinary
M. Karimi Alavijeh, A. S. Meyer, S. L. Gras, S. E. Kentish
Summary: N-Acetyllactosamine (LacNAc) is a unique acyl-amino sugar essential in human milk oligosaccharides and glycoproteins, yet knowledge of large-scale production remains limited. Enzymatic routes, particularly utilizing beta-galactosidases and sialidases, are likely key to commercial production of LacNAc and its derivatives. Optimization of reaction parameters and development of robust enzymes are crucial for enhancing the commercial production of these important bioactive substances.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2021)
Article
Chemistry, Organic
Sijing Wang, Jia Yang, Hongkun Zeng, Yuqiao Zhou, Fei Wang, Xiaoming Feng, Shunxi Dong
Summary: Highly enantioselective formal coupling of beta-ketoesters with quinones was achieved using a chiral bifunctional N-heterocyclic olefin organocatalyst. Enantioenriched quinone derivatives were obtained with good yields, high enantioselectivities, and regioselectivities. The gram-scale synthesis and inhibitory effect on cancer cells demonstrate the potential utility of this method.
Article
Polymer Science
Xiaowei Jiang, Zhihong Liu, Yujiao Tan, Xiaosong Chen, Ping Huang, Libo Ma, Xu Xiong, Weibin Gao, Yu Tao, Hongxia Lu, Zheng Dai
Summary: Flexible nitrogen porous organic polymers (FNPOPs) with high nitrogen content were synthesized using acetic acid as both solvent and catalyst. The materials exhibit moderate BET surface area and excellent thermal stabilities. FNPOP-2 was prepared as phase change material (PCM) composites by self-adsorption method, which showed high encapsulation ratio (55.2 wt%) and latent heat (135.7 J g(-1)) due to its flexible structure and high nitrogen atomic content. Furthermore, the thermal energy storage properties of all PCM composites remained after several thermal cycles. In general, FNPOPs have potential applications in phase change materials adsorption and thermal energy storage.
JOURNAL OF APPLIED POLYMER SCIENCE
(2023)
Article
Chemistry, Physical
Rong Yan, Meiyang Song, Peng Chen, Henghui Song, Chengbing Fu, Haiyang Peng, Shuang-Feng Yin
Summary: A simplified strategy of introducing cyano-functionalized smaller D (benzene) - A (triazine) units in PDI-triazine based polymer (PDIMB) enhanced the intrinsic molecule dipole and built-in electric field, promoting exciton dissociation and charge transfer. PDIMB-2 showed high activity and selectivity for the photooxidation reaction of benzylamine to N-benzylidenebenzylamine under mild conditions.
JOURNAL OF COLLOID AND INTERFACE SCIENCE
(2023)
Article
Chemistry, Organic
Jiaoyang Wang, Danfeng Wang, Xiaofeng Tong
Summary: The MnO2-promoted oxidative coupling process reported in this study provides a mild and scalable method for the synthesis of trisubstituted hydrazine. This new approach is operationally straightforward and can be easily scaled up.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Applied
Jun-Long Zhan, Lin Zhu, Wei Ren, Bing-Jie Wang, Xin-Ming Zhao, Xin-Ru Zhang, Xin-Yu Zhang, Yao-Qiang Xie
Summary: A feasible and umpolung strategy for synthesizing diverse beta-amino ketones was achieved through TEMPO mediated C-N coupling of cyclopropanols with nitrogen nucleophiles. Mechanism studies showed that enones derived from cyclopropanols are key intermediates and TEMPO plays multiple roles. This protocol offers broad substrate scope, good scalability, and good to excellent yields, providing an alternative approach to the synthesis of structurally important beta-amino ketone scaffolds under metal and additive-free conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Biochemistry & Molecular Biology
Dehe Wang, Qichao Lu, Zhanjun Li, Chen Fang, Ran Liu, Bingchuan Yang, Guodong Shen
Summary: Efficient one-pot CuCl2-catalyzed C-S bond coupling reactions were developed for the synthesis of dibenzo[b,f][1,4]thiazepines and 11-methy-ldibenzo[b,f][1,4]thiazepines via 2-iodobenzaldehydes/2-iodoacetophenones with 2-aminobenzenethiols/2,2'-disulfanediyldianilines by using DMEDA as a bifunctional-reagent that worked as a ligand and reductant. The reactions were compatible with a range of substrates and gave moderate to excellent yields.
Article
Biochemistry & Molecular Biology
Lorenzo Pacini, Annunziata D'Ercole, Anna Maria Papini, Daniele Bani, Silvia Nistri, Paolo Rovero
Summary: Despite hindrances in its chronic treatment due to multiple daily IV injections for a long time, the potential of recombinant H2 relaxin or serelaxin as a cardiovascular drug remains. This study focused on investigating the molecular background for the possibility of administering relaxin orally. In vitro digestion of serelaxin and purified porcine relaxin (pRLX) was conducted to simulate gastroprotective formulations. The bioactivity of the intact molecules and their proteolytic fragments was evaluated using second messenger response in relaxin receptor-bearing human monocytic cells. The results suggest the potential development of synthetic relaxin agonists suitable for oral administration.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Biochemistry & Molecular Biology
Michael Quagliata, Francesca Nuti, Feliciana Real-Fernandez, Kalina Kirilova Kirilova, Federica Santoro, Alfonso Carotenuto, Anna Maria Papini, Paolo Rovero
Summary: Multiple sclerosis (MS) is an inflammatory and autoimmune disorder characterized by antibody-mediated demyelination. Glucosylated peptides derived from human myelin proteins, OMGp and RTN4R, were recognized by antibodies in the sera of MS patients, indicating an immunological association between human and bacterial protein antigens. These findings support the hypothesis of molecular mimicry triggering self-tolerance breakdown in MS, suggesting RTN4R and OMGp as autoantigens.
JOURNAL OF PEPTIDE SCIENCE
(2023)
Article
Chemistry, Organic
Poriah Strauss, Francesca Nuti, Michael Quagliata, Anna Maria Papini, Mattan Hurevich
Summary: Peptide fragments of glycoproteins with multiple N-glycosylated sites are important tools for studying protein-protein interactions and developing glycopeptide-based diagnostics and immunotherapy. However, the solid-phase synthesis of glycopeptides with multiple N-glycosylated sites is challenging due to difficult couplings and low yield. In this study, we propose an accelerated synthesis approach, called High-Temperature Fast Stirring Peptide Synthesis (HTFS-PS), using heating, stirring, and low-loading solid supports to obtain glycopeptides with multiple N-glycosylated sites.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Review
Chemistry, Medicinal
Michael Quagliata, Anna Maria Papini, Paolo Rovero
Summary: Eradication of malaria remains one of the main aims of medicine. Recent approval of the first effective vaccine has reinforced the importance of prevention through vaccination. Different types of vaccines targeting specific stages of the parasite cycle, as well as vaccine storage considerations and advanced technologies, can lead to more effective and safer vaccines.
EXPERT OPINION ON THERAPEUTIC PATENTS
(2023)
Article
Biochemistry & Molecular Biology
Patrycja Ledwon, Waldemar Goldeman, Katarzyna Haldys, Michal Jewginski, Greta Calamai, Joanna Rossowska, Anna Maria Papini, Paolo Rovero, Rafal Latajka
Summary: The development of skin-care products, including cosmeceuticals containing proven active ingredients, such as peptides, is on the rise. However, the applicability of whitening agents in these products is often limited due to drawbacks like toxicity and lack of stability. In this study, thiosemicarbazone (TSC)-peptide conjugates were found to inhibit diphenolase activity, and were tested as tyrosinase and melanogenesis inhibitors in B16F0 cells. The results showed that TSC1-conjugates had a lower IC50 value than the widely used reference compound kojic acid, making them potential candidates for tyrosinase inhibition.
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Francesca Nuti, Maud Larregola, Agnieszka Staskiewicz, Bernhard Retzl, Natasa Tomasevic, Lorenzo Macchia, Maria E. Street, Michal Jewginski, Olivier Lequin, Rafal Latajka, Paolo Rovero, Christian W. Gruber, Michael Chorev, Anna Maria Papini
Summary: In this study, a series of C alpha(1)-to-C alpha(6) side chain-to-side chain [1,2,3]triazol-1-yl-containing oxytocin analogues were designed and synthesized. Through in vitro experiments, the conformational analysis and pharmacological activity of these analogues were explored. The macrocyclization approach was employed to increase the stability of oxytocin, and interesting insights into the structure-conformation-function relationship of oxytocin were obtained.
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Michele Casoria, Marina Macchiagodena, Paolo Rovero, Claudia Andreini, Anna Maria Papini, Gianni Cardini, Marco Pagliai
Summary: The standard GAFF2 force field parameterization has been refined for three fluorinated alcohols commonly used to study proteins and peptides in biomimetic media. The newly proposed models are validated through experimental findings, supporting their accuracy and effectiveness.
JOURNAL OF PEPTIDE SCIENCE
(2023)
Review
Biochemistry & Molecular Biology
Michael Quagliata, Anna Maria Papini, Paolo Rovero
Summary: The COVID-19 pandemic caused by the SARS-CoV-2 virus is still a potentially lethal disease, and despite the availability of vaccines and antiviral drugs, there is ongoing search for more specific treatment options. Modified antiviral peptides are a promising class of compounds that can block viral infection at different stages of replication by increasing specificity and affinity. This review provides a useful basis for the design of new and powerful antiviral therapeutics against SARS-CoV-2.
JOURNAL OF PEPTIDE SCIENCE
(2023)
Article
Virology
Maria Alfreda Stincarelli, Michael Quagliata, Andrea Di Santo, Lorenzo Pacini, Feliciana Real Fernandez, Rosaria Arvia, Silvia Rinaldi, Anna Maria Papini, Paolo Rovero, Simone Giannecchini
Summary: In order to combat SARS-CoV-2, researchers have studied the conserved amino acid region of the internal fusion peptide in the Spike glycoprotein of SARS-CoV-2 to design new inhibitory peptides. One of these peptides, PN19, showed powerful inhibitory activity against different SARS-CoV-2 variants without cytotoxicity. The inhibitory activity of PN19 was dependent on the conservation of specific amino acid residues and its binding ability to membrane-proximal region derived peptides. These findings suggest that the internal fusion peptide region is a promising target for developing peptidomimetic antivirals against SARS-CoV-2.
Editorial Material
Chemistry, Multidisciplinary
Irene S. Fahim, Vania Andre, Jyotirmayee Mohanty, Rosalia Maria Cigala, Srabanti Ghosh, Luisa M. D. R. S. Martins, Weiwei Han, Anna Maria Papini, Joana Costa, Maela Manzoli, Ottavia Giuffre, Reshma Rani, Sarish Rehman, Debbie C. Crans, Gabriela Oksdath-Mansilla, Federica Sabuzi
FRONTIERS IN CHEMISTRY
(2023)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
