Article
Chemistry, Multidisciplinary
Jicheng Wu, Peijing Jia, Rositha Kuniyil, Peng Liu, Weiping Tang
Summary: In this study, we report an efficient method for the stereoselective synthesis of challenging α-linked glycoconjugates using a Rh-II/chiral phosphoric acid (CPA)-cocatalyzed dynamic kinetic anomeric O-alkylation. By exploring various parameters of the cocatalytic system, we achieved excellent anomeric selectivity, excellent diastereoselectivity, broad substrate scope, and high efficiency for this glycosylation reaction. DFT calculations suggested that the anomeric selectivity was determined by steric interactions between the C2-carbon of the carbohydrate and the phenyl group of the metal carbenoid, while diastereoselectivity at the newly generated stereogenic center was influenced by π-π interactions with the C2-OBn substituent on the carbohydrate substrate.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Debasish Pal, Aritra Chaudhury, Balaram Mukhopadhyay
Summary: This manuscript reports the chemical synthesis method of the trisaccharide repeating unit of the O-antigen from Pseudomonas putida BIM B-1100. The challenging residues were successfully incorporated through rational protecting group manipulations and a linear strategy, and the desired carboxylic acid moiety was introduced through TEMPO-mediated oxidation. The use of aminoethyl glycoside allows further glycoconjugate formation without affecting the anomeric stereochemistry.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Kameshwar Prasad, Ananay Sharma, Soumyaranjan Pati, Marc Taillefer, Florian Jaroschik, Srinivas Hotha
Summary: We report metal free conditions for the activation of alkynyl glycosyl carbonate donors using I-2/TMSOTf in stoichiometric quantities. The extrusion product was characterized as vinylidene iodide by single crystal X-ray analysis. The reaction conditions were suitable for the synthesis of various glycosides, purine/pyrimidine nucleosides, and a pentasaccharide repeating unit of Klebsiella pneumoniae (O-3 antigen).
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Biophysics
Vanessa E. Abrantes-Coutinho, Andre O. Santos, Rafael B. Moura, Francisco N. Pereira-Junior, Lucia H. Mascaro, Simone Morais, Thiago M. B. F. Oliveira
Summary: Lectin-based biosensors have made significant progress in the field of electroanalysis, offering high sensitivity, specificity, precision, and stability for the detection of clinically relevant carbohydrates and glycoproteins. By combining different materials and functional groups, these sensors can further enhance detection performance and applicability.
COLLOIDS AND SURFACES B-BIOINTERFACES
(2021)
Article
Biochemistry & Molecular Biology
Matteo Cattin, Jean-Francois Bruxelle, Kurtis Ng, Markus Blaukopf, Ralph Pantophlet, Paul Kosma
Summary: This study describes an improved synthesis method for generating epitopes related to oligomannose-type glycans on the spike protein of HIV-1. The results suggest that a complete Man(9) structure might not be the preferred antigenic binding motif for some oligomannose-specific antibodies.
Article
Chemistry, Organic
Md Azadur Rahman, Kana Kuroda, Hirofumi Endo, Norihiko Sasaki, Tomoaki Hamada, Hiraku Sakai, Toshiki Nokami
Summary: The synthesis of protected precursors of chitin oligosaccharides was achieved by electrochemical polyglycosylation of thioglycosides as mono-mer, leading to the successful synthesis of up to hexasaccharides and octasaccharides. The mechanism of this process was discussed based on the oxidation potential of the monomers and oligosaccharides.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Benedicte Ronne Kristensen, Christian Marcus Pedersen
Summary: A self-promoted glycosylation method was developed to selectively form beta-glucosides from a diverse substrate library. This two-component reaction occurs at elevated temperatures without the need for additives or catalysts, providing easy access to glycoconjugates under mild conditions. The influences of neighboring group participation and substituents were investigated, and kinetic data from in situ IR were used for a Hammett study, revealing a correlation between acceptor pK(a) and reaction rate and providing new mechanistic insights.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Janaina Macedo-da-Silva, Veronica F. Santiago, Livia Rosa-Fernandes, Claudio R. F. Marinho, Giuseppe Palmisano
Summary: Extracellular vesicles (EVs) are lipid-bilayer enclosed particles that play crucial roles in intercellular communication, biomolecule delivery, cellular disposal, homeostasis maintenance, potential biomarkers, and drug carriers. The content of EVs, which includes DNA, lipids, metabolites, proteins, and microRNA, has been studied in various diseases, showcasing their significance in disease pathology and treatment.
MOLECULAR IMMUNOLOGY
(2021)
Article
Chemistry, Organic
Miao Liu, Zhao-Xiang Luo, Tian Li, De-Cai Xiong, Xin-Shan Ye
Summary: A new electrochemical approach for trifluoromethylation of glycals using CF3SO2Na and MnBr2 has been reported, resulting in trifluoromethylated glycals with different protective groups in high yields. The successful capture of a CF3 radical suggests a radical mechanism is involved in this reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Akito Shibuya, Moeko Kato, Asuka Saito, Sujit Manmode, Naoto Nishikori, Toshiyuki Itoh, Aiichiro Nagaki, Toshiki Nokami
Summary: This study found that the stability of glycosyl dioxalenium ions can be enhanced by introducing tert-butyldiphenylsilyl group at 6-OH, allowing reactions to be performed at elevated temperatures. NMR and VT-NMR measurements revealed the impact of protecting groups on the stability of intermediates, leading to the successful synthesis of a trisaccharide with a glucoside β-1,6 linkage.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Masahiro Takumi, Hodaka Sakaue, Aiichiro Nagaki
Summary: A novel flow electrochemical reactor has been developed to achieve electrolysis within a few seconds and enable reaction with nucleophiles before the decomposition of short-lived carbocations. Furthermore, continuous operation based on this system allows for rapid synthesis of pharmaceutical precursors on demand.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Biochemistry & Molecular Biology
Sophie Groux-Degroote, Dorothee Vicogne, Virginie Cogez, Celine Schulz, Anne Harduin-Lepers
Summary: The study focused on the expression of blood group carbohydrate antigens Sd(a) and SLe(x) in normal and cancerous colonic tissues, as well as the potential prognostic value of high levels of B4GALNT2 gene expression in colon cancer. Despite the association between elevated B4GALNT2 expression and better prognosis, the molecular mechanisms regulating the expression of these carbohydrate antigens remain poorly understood.
Article
Chemistry, Multidisciplinary
Hirofumi Endo, Masaharu Ochi, Md Azadur Rahman, Tomoaki Hamada, Takahiro Kawano, Toshiki Nokami
Summary: Unnatural cyclic oligosaccharides composed of N-acetylglucosamine with alpha-1,4-glycosidic linkages have been successfully synthesized using electrochemical synthesis. The study also demonstrated that this method can be utilized for the isomerization of linear oligosaccharides and intramolecular glycosylation for cyclization.
CHEMICAL COMMUNICATIONS
(2022)
Article
Electrochemistry
Navaneeth Punnakkal, Jeethu Raveendran, Suneesh Punathil Vasu, Bipin G. Nair, T. G. Satheesh Babu
Summary: The electrochemical detection of cholesterol was carried out using pencil lead electrode in acetonitrile and acetone solution with lithium perchlorate. The PLE exhibited a wide linear detection range and high sensitivity, with high specificity to cholesterol in the presence of interfering biomolecules. Calibration plots for real samples showed a highly linear response in both serum and skin cholesterol samples.
JOURNAL OF THE ELECTROCHEMICAL SOCIETY
(2021)
Article
Environmental Sciences
Mengze Geng, Xin Huang, Baoyou Shi, Jianwei Yu, Chunmiao Wang, Yuning Du, Yili Wang
Summary: The swampy/septic odor caused by thioethers is a major taste and odor problem in China's drinking water. Pre-oxidation has been found to improve the coagulation performance of thioethers, increasing their removal rates by 1.5 to 3 times. Bovine serum albumin (BSA) as background dissolved organic matter (DOM) enhances the removal efficiency of thioethers compounds compared to humic acid (HA), and the binding effect between BSA and thioethers compounds is mainly due to van der Waals forces and hydrogen bond. Therefore, pre-ozonation combined with coagulation is suggested for better control of thioethers compounds.
SCIENCE OF THE TOTAL ENVIRONMENT
(2023)
Article
Biochemistry & Molecular Biology
Agnieszka Hryniewicka, Katarzyna Niemirowicz-Laskowska, Przemyslaw Wielgat, Halina Car, Tomasz Hauschild, Jacek W. Morzycki
Summary: The novel dehydroepiandrosterone-derived imidazolium salts exhibit high antimicrobial activity against Gram-positive bacteria and Candida albicans, with good compatibility with host cells. Additionally, these compounds have immunoprotective properties.
BIOORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Juan A. Rivas-Loaiza, Aneta Baj, Yliana Lopez, Stanislaw Witkowski, Agnieszka Wojtkielewicz, Jacek W. Morzycki
Summary: The paper presents a simple synthesis method of Demissidine stereoisomers and analogues from a common steroidal sapogenin tigogenin. Different stereoisomers and compounds were obtained through step-by-step transformation or direct reductive amination in the synthesis process.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Urszula Kielczewska, Radek Jorda, Gabriel Gonzalez, Jacek W. Morzycki, Haresh Ajani, Katarina Svrckova, Sarka Stepankova, Agnieszka Wojtkielewicz
Summary: The newly synthesized solasodine analogues act as non-competitive inhibitors of acetyl- and butyryl-cholinesterases, showing potential neuroprotective effects without neurotoxicity. They are able to inhibit and bind cholinesterases, exhibiting the ability to increase cell viability in neuroprotective assays compared to standard drugs.
JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY
(2021)
Article
Biochemistry & Molecular Biology
Anna Puckowska, Magdalena Gawel, Marlena Komorowska, Pawel Drozdzal, Aleksandra Arning, Damian Pawelski, Krzysztof Brzezinski, Marta E. Plonska-Brzezinska
Summary: Derivatives based on pyridine-2-6- and furan-2,5-dicarboxamide scaffolds have diverse chemical properties and biological activities, making them a significant research topic in supramolecular and coordination chemistry, as well as in the discovery of new pharmacologically-active compounds. This study aimed to synthesize a series of symmetrical pyridine-2-6- and furan-2,5-dicarboxamides through the condensation reaction of appropriate acyl chlorides and aromatic amides. Successful syntheses were confirmed using NMR spectroscopy. Crystal structures of seven compounds, including two pyridine and five furan derivatives, were determined, revealing their supramolecular features. Hirshfeld surface analysis provided insights into the distribution of intermolecular contacts within the dicarboxamide crystals.
Article
Biochemistry & Molecular Biology
Diana Sawicka, Agnieszka Hryniewicka, Sylwia Gohal, Anna Sadowska, Anna Pryczynicz, Katarzyna Guzinska-Ustymowicz, Emilia Sokolowska, Jacek W. Morzycki, Halina Car
Summary: This research evaluated a series of novel imidazolium salts substituted with lithocholic acid and alkyl chains of various lengths against colon cancer cells. The results showed that these salts have anticancer activity, which is related to the length of the alkyl chain. The study also demonstrated the inhibitory effect of one compound on tumor growth in a mouse model.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Biochemistry & Molecular Biology
Jakub W. Strawa, Katarzyna Jakimiuk, Lukasz Szoka, Krzysztof Brzezinski, Pawel Drozdzal, Jerzy A. Palka, Michal Tomczyk
Summary: This study isolated four new compounds and three known compounds from the aerial parts of Hottonia palustris, and investigated their chemical structures and biological activities. The compounds showed potential inhibitory effects on the proliferation of oral squamous carcinoma cells, suggesting their potential for further development as therapeutics for oral squamous cell carcinoma.
Article
Biochemical Research Methods
Joanna Loch, Agnieszka Klonecka, Kinga Kadziolka, Piotr Bonarek, Jakub Barciszewski, Barbara Imiolczyk, Krzysztof Brzezinski, Miroslaw Gilski, Mariusz Jaskolski
Summary: This work reports the results of random mutagenesis of Escherichia coli class 2 l-asparaginase EcAIII and the study of new variants using structural, biophysical, and bioinformatic methods. The experiments revealed that the EcAIII fold can accept different types of mutations with varied impacts on protein thermal stability. Important findings include the adaptability of the EcAIII fold to new substitutions, the role of Arg207 in EcAIII activity, and the complexity of the autoprocessing reaction. These insights provide valuable information for enzyme-engineering experiments aimed at designing therapeutic proteins, especially l-asparaginases for leukemia therapy.
ACTA CRYSTALLOGRAPHICA SECTION D-STRUCTURAL BIOLOGY
(2022)
Article
Biochemical Research Methods
Piotr H. Malecki, Barbara Imiolczyk, Jakub Barciszewski, Justyna Czyrko-Horczak, Joanna Sliwiak, Magdalena Gawel, Katarzyna Wozniak, Mariusz Jaskolski, Krzysztof Brzezinski
Summary: The mesophilic cyanobacterium Synechocystis sp. PCC 6803 encodes an S-adenosyl-l-homocysteine hydrolase (SAHase) of archaeal origin in its genome. Unlike other bacterial SAHases, the activity and ligand binding of SynSAHase are not affected by specific alkali ions, and it exists in an equilibrium of dimeric and tetrameric forms in solution.
ACTA CRYSTALLOGRAPHICA SECTION D-STRUCTURAL BIOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Aneta Baj, Nirawit Kaewnok, Juan A. Rivas-Loaiza, Magdalena Szymanska, Stanislaw Witkowski, Agnieszka Wojtkielewicz, Jacek W. Morzycki
Summary: A simple synthesis method for solanidane alkaloids from common steroidal sapogenins was developed. The previously described multi-step transformations were shortened to only four steps by focusing on the key-step of epimerization at C25. Different approaches to this reaction were investigated and it was found that the epimerization step is unnecessary if the starting sapogenin has the same configuration at C25 as the target alkaloid. This enabled the synthesis of related solanidane alkaloids with retention of configuration at this stereogenic center in a three-step procedure.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Biochemistry & Molecular Biology
Aneta M. Tomkiel, Dorota Czajkowska-Szczykowska, Ewa Olchowik-Grabarek, Lucie Rarova, Szymon Sekowski, Jacek W. Morzycki
Summary: A chemoselective procedure was developed to oxidize 26-thiodiosgenin to sulfoxides and sulfones. Surprisingly, an unusual equilibration of sulfoxides was observed in solution. Additionally, the alpha-alkylation of sulfoxides and sulfones was investigated, followed by the examination of the biological activity of the obtained compounds.
Article
Plant Sciences
Malgorzata Marszalek-Zenczak, Anastasiia Satyr, Pawel Wojciechowski, Michal Zenczak, Paula Sobieszczanska, Krzysztof Brzezinski, Tetiana Iefimenko, Marek Figlerowicz, Agnieszka Zmienko
Summary: Metabolic gene clusters (MGCs) are groups of genes involved in a common biosynthetic pathway. They can lead to intraspecies variation and cause phenotypic diversity. The study examined copy number variations (CNVs) in four Arabidopsis thaliana MGCs and found that different gene clusters displayed varying levels of diversity and conservation. The study identified a large genomic insertion containing divergent duplicates of specific genes and discovered gene expression alterations and phenotypic differences associated with these duplications.
FRONTIERS IN PLANT SCIENCE
(2023)
Article
Biochemical Research Methods
Pawel Drozdzal, Tomasz Manszewski, Miroslaw Gilski, Krzysztof Brzezinski, Mariusz Jaskolski
Summary: The self-complementary L-d(CGCGCG)(2) hexanucleotide, which contains the enantiomeric 2'-deoxy-L-ribose, forms a right-handed Z-DNA duplex when crystallized in complex with cadaverine and potassium cations. The ultrahigh-resolution crystal structure at 0.69 angstrom resolution confirmed the right-handed structure. Mistakenly assuming the presence of 2'-deoxy-D-ribose, the X-ray diffraction data revealed the wrong hand of the structure due to the weak anomalous signal of P and K atoms. The crystal structure also showed the interaction of the cadaverinium dication and K+ cation with the Z-DNA duplex.
ACTA CRYSTALLOGRAPHICA SECTION D-STRUCTURAL BIOLOGY
(2023)
Article
Multidisciplinary Sciences
Agnieszka Hryniewicka, Joanna Breczko, Gabriela Siemiaszko, Anthony N. Papathanassiou, Kinga Gora-Marek, Karolina A. Tarach, Krzysztof Brzezinski, Anna Ilnicka, Artur P. Terzyk, Karolina H. Markiewicz, Luis Echegoyen, Marta E. Plonska-Brzezinska
Summary: Covalent triazine-based frameworks have received significant attention recently due to their high surface area and excellent thermal and electrochemical stabilities. This study demonstrates that immobilizing triazine-based structures on carbon nanostructures results in the formation of micro- and mesopores in a three-dimensional manner. The combination of spherical carbon nanostructures and the triazine framework leads to a material with unique physicochemical properties and the highest specific capacitance value in aqueous acidic solutions. This hybrid system shows promise for electrochemical applications.
SCIENTIFIC REPORTS
(2023)
Article
Materials Science, Multidisciplinary
Agnieszka Hryniewicka, Joanna Breczko, Gabriela Siemiaszko, Krzysztof Brzezinski, Anna Ilnicka, Artur P. Terzyk, Marta E. Plonska-Brzezinska
Summary: Covalent triazine frameworks (CTFs) are a promising class of high-performance materials due to their porosity and structural control at the molecular or atomic level. However, their use as supercapacitor electrodes is limited by low electrical conductivity and stacking effect. This study successfully synthesized hybrid carbon nano-onion-based CTFs, which exhibited significantly higher specific capacitance values compared to reference CTFs. This strategy expands the scope and application of CTFs as electrode materials for electrochemical energy storage systems.
MATERIALS ADVANCES
(2023)
Article
Chemistry, Multidisciplinary
Gabriela Siemiaszko, Agnieszka Hryniewicka, Joanna Breczko, Krzysztof Brzezinski, Marta E. Plonska-Brzezinska
Summary: In this study, mesoporous carbon materials were synthesized from diblock star copolymers derived from polyacrylonitrile. The size of the pores was controlled by manipulating the length of the polymer blocks. Furthermore, the organization of polymers on the carbon nano-onion's surface resulted in materials with higher surface area and superior electrochemical performance.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
