Article
Chemistry, Multidisciplinary
Jaggaiah N. Gorantla, Maniganda Santhi, Yanling Hua, James R. Ketudat Cairns
Summary: This study discovered an acyl migration-dependent method for synthesis by using appropriate blocking groups, which turns acyl migration into a tool for synthesis rather than an impediment.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Verena Sukowski, Manuela van Borselen, Simon Mathew, M. Angeles Fernandez-Ibanez
Summary: By reversing conventional site-selectivity of C-H activation, a new catalytic system based on palladium/norbornene and an S,O-ligand for meta-C-H arylation of aryl ethers is reported, which outperforms previously reported systems. This system shows unique ability to use alkoxyarene substrates with different substituents, as well as tolerate ortho-substituted aryl ethers by employing novel norbornene mediators. Moreover, monoarylation of alkoxyarenes is achieved for the first time, enabling rapid introduction of a second, different aryl coupling partner.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Michael R. Smith, Le Zhang, Yizhen Jin, Min Yang, Anusha Bade, Kevin D. Gillis, Sadhan Jana, Ramesh Naidu Bypaneni, Timothy E. Glass, Hening Lin
Summary: Maintaining the balance of amino acids is important for cell survival and dysfunction of nutrient balance can lead to diseases such as diabetes. In this study, a novel fluorescent sensor called NS560 was developed to detect 18 proteogenic amino acids in mammalian cells. By using NS560, amino acid pools were identified in lysosomes, late endosomes, and near the rough endoplasmic reticulum. Furthermore, the study revealed that Cathepsin L (CTSL) is the target of chloroquine, leading to the accumulation of amino acids in large cellular foci.
ACS CENTRAL SCIENCE
(2023)
Article
Biochemistry & Molecular Biology
Zhipeng Liang, Ya-Nan Wu, Yang Wang
Summary: In this study, a novel S(O)(2)-N coupling reaction was developed for the synthesis of sulfonamide compounds under mild conditions, utilizing visible light catalysis and dual copper catalysis. Furthermore, the reaction takes advantage of visible light-induced azides to generate triplet nitrene, allowing for the efficient synthesis of structurally diverse benzenesulfinamides in good yields.
Article
Biochemistry & Molecular Biology
Corentin Maret, Nicolas David, David Pierrot, Eric Leonel, Vincent Levacher, Jean-Francois Briere, Sylvain Oudeyer
Summary: The electrocarboxylation of alpha,alpha-dichloroarylmethane derivatives in the presence of CO2 was achieved, resulting in the formation of alpha-chloroarylacetic acid derivatives with high selectivity. These derivatives were found to be versatile intermediates in synthetic chemistry and underwent various chemical transformations. A proposed mechanism was supported by control experiments and cyclic voltammetry.
Article
Chemistry, Organic
Jiamin Wu, Jinli Zhang, Yongjuan Jiao, Gongtao Deng, Yingmei Li, Zhengyu Zhang, Yaojia Jiang
Summary: A unique decarbonylation of an amino acid derivative catalytic system has been developed via palladium-catalyzed C-C bond and C-N bond dual activations. This approach provides a straightforward avenue for constructing diverse functionalized amide compounds in good to excellent yields. The proposed reaction pathway may involve C-C bond and C-N bond dual activations based on mechanistic studies.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Tianqi Du, Kimiyoshi Kaneko, Yuki Sakai, Masato Tsunoi, Tenchi Yoshitake, Aki Kotera, Yasuyuki Matsushima, Tsuyoshi Miura, Tetsuya Kajimoto
Summary: In this study, terpenyl 2,3,4-tri-O-acetyl-alpha- D-glucuronide methyl esters were facilely synthesized in good yields using commercially available materials and Tf2NH as a catalyst in dichloromethane. The alpha-selectivity at the anomer position was primarily achieved through the stabilization of the oxonium intermediate by neighboring group participation of the methoxycarbonyl group at C-6. This acceleration of the glucuronidation reaction was unexpected given the use of the acetyl group as the activating group.
CHEMICAL & PHARMACEUTICAL BULLETIN
(2022)
Article
Chemistry, Organic
Yuan-Yuan Gao, Chun-Lin Zhang, Lei Dai, You-Feng Han, Song Ye
Summary: The unprecedented dynamic kinetic resolution (DKR) of hemiaminals without alpha-hydrogen was developed via N-heterocyclic carbene catalyzed O-acylation, resulting in high yields of esters with good to high enantioselectivities.
Article
Chemistry, Organic
Koichi Mitsudo, Yasuyuki Okumura, Kotaro Yohena, Yuji Kurimoto, Eisuke Sato, Seiji Suga
Summary: Electrochemical dehydrogenative C-O bond formation was achieved for the synthesis of sultones. In the presence of K2CO3 and H2O, constant current electrolysis of [1,1'-biphenyl]-2-sulfonyl chloride resulted in quantitative formation of aryl-fused sultone. Control experiments suggest that electrochemical oxidation of sulfonates generates sulfo radical intermediates.
Article
Chemistry, Multidisciplinary
Giuseppe Zuccarello, Suzanne M. Batiste, Hyungdo Cho, Gregory C. Fu
Summary: Due to increasing interest in the pharmaceutical industry, the synthesis of chiral alpha-aminoboronic derivatives has become an important challenge. In this study, we demonstrate the enantioselective synthesis of these derivatives using a chiral copper catalyst generated from commercially available components. Mechanistic studies were also conducted to optimize the process and provide insights into the reaction mechanism.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Sheng Guo, Timothy M. Swager
Summary: POPs and PAEs are versatile polymer materials with porous properties and high performance characteristics. A new synthetic method has been developed for the preparation of PAEs, allowing for a wider range of compositions and architectures. These porous PAEs are solution processable and have potential applications in heavy-metal-ion sensing and capture.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Manon Genet, Abdelilah Takfaoui, Jerome Marrot, Christine Greck, Xavier Moreau
Summary: An enantioselective organocatalytic reaction of indole-derived-1-azadienes with aldehydes has been reported, leading to the formation of enantioenriched cyclic N,O-acetals. The corresponding products can be obtained with high levels of stereoselectivity, and fused tetracyclic scaffolds can also be obtained using a one-pot strategy.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Shutao Wang, Lianyou Zheng, Shaoli Song, Siyu Wang, Zhuoqi Zhang, Jinbao Xiang
Summary: A controllable and regiodivergent N-allylation reaction has been developed using O-alkyl hydroxamates derived from natural alpha-amino acids, enabling specific synthesis of alpha/beta-dipeptides containing unsaturated beta-amino acid moieties in moderate to good yields. The regioselectivity can be conveniently altered by changing the catalysts and solvents.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Tian-Yu Peng, Zhe-Yuan Xu, Feng-Lian Zhang, Bin Li, Wen-Ping Xu, Yao Fu, Yi-Feng Wang
Summary: A strategically distinct dehydroxylative alkylation reaction of alpha-hydroxy carboxylic acid derivatives with alkenes has been developed. The reaction involves the attack of a 4-dimethylaminopyridine (DMAP)-boryl radical to the carbonyl oxygen atom, followed by a spin center shift (SCS) to initiate C-O bond scission. The resulting alpha-carbonyl radicals then couple with a wide range of alkenes, leading to various alkylated products. This strategy allows for the efficient conversion of alpha-hydroxy amides and esters derived from biomass molecules and natural products into valuable compounds. Experimental and computational studies have confirmed the reaction mechanism.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Xinghua Zhang, Shuang Xu, Xiang Yang, Wan Pang
Summary: A novel method for the synthesis of allylic sulfones via direct allylic C-H bond activation of alpha-methylstyrene derivatives with sulfonylhydrazines under metal-catalyst-free electrochemical conditions has been developed. By utilizing electron transfer in the current instead of stoichiometric chemical oxidants, a wide range of valuable allylic sulfones were obtained with excellent regioselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Medicinal
Arvind Negi, Paul Murphy
Summary: Mcl-1, an anti-apoptotic protein, plays a crucial role in cancer cell survival and is a promising target for cancer therapy. Various inhibitors targeting Mcl-1 have been designed, but none have been approved for clinical use. This review summarizes the structures and structure-activity relationships of Mcl-1 inhibitors, highlighting their potential in cancer treatment.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Multidisciplinary Sciences
Paul Murphy, Antonio Romero, Qi Xiao, Anna-Kristin Ludwig, Srinivas Jogula, Nadezhda Shilova, Tanuja Singh, Adele Gabba, Bilal Javed, Dapeng Zhang, Francisco J. Medrano, Herbert Kaltner, Jurgen Kopitz, Nicolai Bovin, Albert M. Wu, Michael L. Klein, Virgil Percec, Hans-Joachim Gabius
Summary: The study reveals the mechanism of connection between sulfatides and specific glycoproteins, highlighting the importance of the head group in the functionality of bio-membranes intracellularly and on the cell surface.
Article
Biochemistry & Molecular Biology
Adele Gabba, Agnieszka Bogucka, John G. Luz, Ana Diniz, Helena Coelho, Francisco Corzana, Francisco Javier Canada, Filipa Marcelo, Paul Murphy, Gabriel Birrane
Summary: The MGL protein is an important immunoregulatory receptor that can bind a variety of glycans, with a preference for the glycan GalNAc. New structural studies provide insights into substrate recognition by MGL.
Review
Biochemistry & Molecular Biology
Hans-Joachim Gabius, Mare Cudic, Tammo Diercks, Herbert Kaltner, Jurgen Kopitz, Kevin H. Mayo, Paul V. Murphy, Stefan Oscarson, Rene Roy, Andreas Schedlbauer, Stefan Toegel, Antonio Romero
Summary: The text emphasizes the importance of the sugar code, highlighting the diversity of sugars and the specificity in recognition processes. The enormous potential of glycan biosynthetic enzymes and the development of sugar receptors lay the foundation for understanding the sugar code.
Article
Cell Biology
Anna-Kristin Ludwig, Malwina Michalak, Adele Gabba, Tanja J. Kutzner, Donella M. Beckwith, Forrest G. FitzGerald, Gabriel Garcia Caballero, Joachim C. Manning, Mark Kriegsmann, Herbert Kaltner, Paul Murphy, Mare Cudic, Juergen Kopitz, Hans-Joachim Gabius
Summary: Wild-type lectins have distinct modular designs. This study explores the effects of homodimers and heterodimers of galectins on cell binding properties and activities. The results show that heterodimers exhibit altered properties, with the arrangement of lectin domains and linker length affecting effector activity.
HISTOCHEMISTRY AND CELL BIOLOGY
(2021)
Article
Immunology
Simone Marcella, Sam Afoullouss, Olivier P. Thomas, A. Louise Allcock, Paul Murphy, Stefania Loffredo
Summary: Characellide A and B are novel glycolipopeptides isolated from deep sea sponges, which have the ability to induce cytokine and chemokine release from human PBMC. The study also found that the cytokine release induced by characellide A is CD1d-dependent, indicating its potential role in modulating adaptive/innate immune responses. Further research is needed to explore its pharmacological applications.
INFLAMMOPHARMACOLOGY
(2021)
Article
Chemistry, Organic
Fiach B. Meany, Sarah O'Rourke, Paul Murphy
Summary: The alkene functionalized 2-aminobenzimidazole ring found in terrazoanthine natural products was synthesized in 3 steps from 1,2-epoxy-4-vinylcyclohexane.
Editorial Material
Chemistry, Multidisciplinary
Paul Murphy, Namakkal G. Ramesh
Article
Chemistry, Organic
Liam S. Fitzgerald, Ciaran O'Malley, Paul Murphy
Summary: The synthesis route and structure of a polyhydroxylated 1,4 lactone compound were confirmed through reactions and analyses.
Article
Biochemistry & Molecular Biology
Debashis Dhara, Ashis Dhara, Paul V. Murphy, Laurence A. Mulard
Summary: Chemical synthesis of glycans faces challenges in global deprotection steps, including removal of protecting groups and functional group conversions. This review focuses on representative global deprotection methods such as hydrogenolysis of benzyl groups, saponification of esters, and oxidation/reduction.
CARBOHYDRATE RESEARCH
(2022)
Article
Chemistry, Organic
Arvind Negi, Styliana I. Mirallai, Saidulu Konda, Paul V. Murphy
Summary: An optimized method for the synthesis of various triarylpyridines, including non-symmetric pyridines, with different aryl substituents was reported. The reaction involved sequential addition of two different acetophenones to benzylamine in the presence of copper (I) iodide, methanolic ammonia, and oxygen, resulting in good yields of the desired products.
Article
Biochemistry & Molecular Biology
Arpita Roy, Sylvester Byrne, Nirod Kumar Sarangi, Paul V. V. Murphy, Tia E. Keyes
Summary: This study investigates the mechanism of virulence of Influenza A viruses (IAVs) and the potential treatment with anti-IAV agents using a biophysical platform. The results show that the multivalent interactions of the HA glycoprotein affect the resistance, capacitance, and diffusivity of the host cell membrane. Inhibition of HA glycoprotein association with the host mimetic surface by sialic acid-based inhibitors is observed, although complete prevention of host binding is not achieved.
FRONTIERS IN MOLECULAR BIOSCIENCES
(2022)
Article
Biochemistry & Molecular Biology
Joachim C. Manning, Veronica Baldoneschi, Laura L. Romero-Hern, Katharina M. Pichler, Gabriel GarcIa Caballero, Sabine Andr, Tanja J. Kutzner, Anna-Kristin Ludwig, Valerio Zullo, Barbara Richichi, Reinhard Windhager, Herbert Kaltner, Stefan Toegel, Hans-Joachim Gabius, Paul V. Murphy, Cristina Nativi
Summary: Pairing glycans with tissue lectins can regulate multiple effector pathways in (patho)physiology, and it is particularly important in the progression of osteoarthritis. Designing inhibitors that can block galectin binding and matrix metalloproteinases (MMPs) has the potential to dissect the roles of lectins and proteolytic enzymes. Testing these inhibitors on clinical material has shown promising results in reducing galectin binding to osteoarthritis specimens.
BIOORGANIC & MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Arvind Negi, Paul Murphy
Summary: The human myeloid leukemia cell differentiation protein (hMcl-1) has been identified as a key drug target in blood cancers. However, most hMcl-1 inhibitors have off-target activity towards other members of the Bcl-2 protein family. To improve inhibitor design, researchers have focused on natural hMcl-1 inhibitors and evaluated their binding using multiple receptor and ligand conformations. The docking methods were assessed for their ability to reproduce crystal conformations and predict binding affinities.
CHEMISTRY-SWITZERLAND
(2022)
Article
Chemistry, Organic
Sinclair Sweeney, Patrick McArdle, Bartlomiej Taciak, Stefania Robakiewicz, Magdalena Krol, Paul Murphy
Summary: In this study, one acyclic and four macrocyclic analogs of migrastatin with an E-alkene at C-3 were synthesized using ring-closing metathesis, resulting in mixtures of stereoisomeric alkenes. The crystal structure of a macrolactam with an E-alkene at C-3 and Z-alkene at C-8 was determined, and amide rotamers were observed by NMR spectroscopy. Preliminary in vitro biological study suggested that these new compounds may have limited potential as inhibitors of tumor cell migration.
