Article
Biochemistry & Molecular Biology
Anurag Noonikara-Poyil, Alvaro Munoz-Castro, H. V. Rasika Dias
Summary: This study describes the isolation and full characterization of a thermally stable, copper(I) acetylene complex using a highly fluorinated bis(pyrazolyl)borate ligand support, as well as the details of a related copper(I) complex. Raman data show significant red-shifts in C equivalent to C stretch of different alkynes bound to copper(I), with computational analysis indicating that the interaction is primarily of the electrostatic character. The study also highlights the catalytic activity of a mononuclear copper complex in [3 + 2] cycloadditions and compares its effectiveness with a trinuclear copper catalyst.
Article
Chemistry, Organic
Salvatore Vincenzo Giofre, Matteo Tiecco, Angelo Ferlazzo, Roberto Romeo, Gianluca Ciancaleoni, Raimondo Germani, Daniela Iannazzo
Summary: Natural deep eutectic solvents (NADESs) were used as reaction media in copper-catalyzed azide-alkyne cycloaddition reactions (CuAAc) in this study, showing high efficiency and excellent yields. NADESs demonstrated strong reducing capabilities without the need for added bases and stabilized copper catalytic intermediates through hydrogen bonding.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Miao Wang, Chau Ming So
Summary: A newly developed phosphine ligand with a C2-cyclohexyl group on the indole ring was successfully applied in a chemoselective Sonogashira coupling reaction, achieving an inversion of the conventional chemoselectivity order. This study also provided an efficient approach to the synthesis of polycyclic aromatic hydrocarbons (PAHs) and the natural product analogue.
Review
Chemistry, Multidisciplinary
Manoj K. Jaiswal, Vinod K. Tiwari
Summary: Click Chemistry is a modular, rapid, and reliable tool used for the regioselective 1,2,3-triazole forming [3+2] reaction of organic azide and terminal alkyne. It is widely explored in various emerging research domains. The intramolecular click chemistry, which involves metal-catalyzed cyclization, organo-catalyzed cyclization, and thermal-induced topochemical reaction, is less addressed compared to the intermolecular metal variant. Recent approaches on intramolecular azide-alkyne cycloaddition 'Click Chemistry' and their emerging applications in the development of diverse molecules are reported.
Article
Chemistry, Organic
T. Moritz Weber, Joerg Pietruszka
Summary: Copper-catalyzed alkyne azide click chemistry (CuAAC) is important for drug development and biological materials labeling. A new tridentate Cu-ligand called TDETA was synthesized as a scalable and non-toxic alternative to HN3 and the previously used DTEA ligand. TDETA showed excellent solubility in organic solvents and aqueous solutions, outcompeted commercial ligands THPTA and TBTA for various azide and alkyne combinations using Cu(I) and Cu(II) species, and had a 80% recovery yield.
SYNTHESIS-STUTTGART
(2023)
Article
Biochemistry & Molecular Biology
Joshua Osuofa, Scott M. Husson
Summary: Protein A chromatography is the preferred method for purifying Fc-based proteins, and convective chromatography technologies such as membrane adsorbers can improve throughput. This study demonstrates the use of copper-free click chemistry to prepare Protein A membranes, which showed high binding capacity and concentration for polyclonal human immunoglobulins (hIgG).
Article
Chemistry, Organic
Michael J. Holzmann, Namrata Khanal, Pavel Yamanushkin, Brian Gold
Summary: Cycloalkynes and their utilization in chemical reactions offer promising opportunities, but the design and synthesis of stable reagents with suitable reactivity is still challenging. By incorporating an endocyclic sulfate group, a new class of cycloalkynes with increased stability and reactivity can be obtained.
Review
Chemistry, Multidisciplinary
Didier A. Bilodeau, Kaitlyn D. Margison, Mariam Serhan, John Paul Pezacki
Summary: Bioorthogonal chemical reactions involving nitrones have been optimized for efficient incorporation of unnatural functionality into living systems, with fast reaction rates. These reactions provide versatile tools for probing biological systems and have potential applications in biology.
Article
Chemistry, Organic
Dahye Kang, Conrad Wahl, Justin Kim
Summary: A new class of push-pull-activated alkynes featuring di- and trifluorinated ynol ethers was synthesized. The difluorinated ynol ether displayed an optimal balance of stability and reactivity, while the trifluorinated ynol ether was highly reactive but unstable towards thiols. These fluorinated ynol ethers highlight the importance of the hyperconjugation-rehybridization effect and substituent effects in activating and stabilizing alkynes for bioorthogonal reactivity.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Giulia Brufani, Federica Valentini, Gabriele Rossini, Luigi Carpisassi, Daniela Lanari, Luigi Vaccaro
Summary: We report a multi-step flow protocol for the synthesis of 1,4-disubstituted 1,2,3-triazoles starting from alpha,beta-unsaturated carbonyls. The best results were obtained using a sequential combination of two flow reactors: one packed with a tailor-made POLITAG-F organocatalytic system and a copper tube apparatus. The use of aqueous acetonitrile azeotrope led to excellent catalytic performances in both processes while minimizing waste.
Article
Polymer Science
Chin-Yun Lee, Shu-Man Hu, Jia-Qi Xiao, Yu-Ming Chang, Tatsuya Kusanagi, Ting-Ying Wu, Ya-Ru Chiu, Yen-Ching Yang, Chao-Wei Huang, Hsien-Yeh Chen
Summary: 】The study fabricated methyl propiolate-functionalized porous poly-p-xylylene material through a unique vapor sublimation and deposition process, preserving the functionality and reactivity of methyl propiolate. This material exhibited efficient alkynes as click azide-terminated molecules under copper-free and mild conditions, with specific covalent attachment towards azide-terminated target molecules, presenting potential for various new applications.
Article
Chemistry, Multidisciplinary
Jesus M. Dones, Nile S. Abularrage, Namrata Khanal, Brian Gold, Ronald T. Raines
Summary: The study integrated two strategies to optimize alkynyl reagents for achieving high reaction rates. Computational analysis indicated that aryl substitution could be beneficial for increasing reactivity. Experimental results showed that interactions between the new reagents and amino dipolarophile contribute to enhanced reaction efficiency.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Inorganic & Nuclear
Yu-Hsuan Shen, Alec M. Esper, Ion Ghiviriga, Khalil A. Abboud, Kirk S. Schanze, Christian Ehm, Adam S. Veige
Summary: Combining strain-promoted azide-alkyne cycloaddition (SPAAC) and inorganic click (iClick) reactivity allows access to metal 1,2,3-triazolates. Experimental and computational insights reveal that the iClick reactivity of metal azides depends on the accessibility of the azide functionality rather than electronic effects. Sterically unencumbered azide functionalities exhibit SPAAC iClick reactivity with cyclooctyne.
DALTON TRANSACTIONS
(2021)
Article
Polymer Science
Ozge Ozukanar, Emrah Cakmakci, Ozgun Daglar, Hakan Durmaz, Volkan Kumbaraci
Summary: The study investigated the use of eugenol as a bio-based building block for the preparation of thermoset materials. By combining thiol-ene photopolymerization and thermal azide-alkyne cycloaddition click reactions, eugenol-based coatings with P-, N-, and Si-containing networks were successfully synthesized. These coatings showed excellent thermal stability, optical transparency, pendulum hardness, solvent resistance, and adhesion performance. They also exhibited high gel content and char yield, and resistance to acidic and basic conditions as well as solvents.
EUROPEAN POLYMER JOURNAL
(2023)
Review
Chemistry, Physical
Chang-Qing Qin, Cheng Zhao, Guo-Shu Chen, Yun-Lin Liu
Summary: Catalytic enantioselective azide-alkyne cycloaddition (E-AAC) is an efficient technology for constructing diverse chiral triazoles, with applications in synthetic and medicinal chemistry, biological chemistry, and materials science. Significant developments have been made in copper-, nickel-, iridium-, and rhodium-catalyzed E-AAC reactions in the past six years. This review summarizes these advancements according to different strategies implemented.
Article
Biochemistry & Molecular Biology
Yoan Brissonnet, Romulo Araoz, Rui Sousa, Lucie Percevault, Sami Brument, David Deniaud, Denis Servent, Jean-Yves Le Questel, Jacques Lebreton, Sebastien G. Gouin
BIOORGANIC & MEDICINAL CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Yoan Brissonnet, Coralie Assailly, Amelie Saumonneau, Julie Bouckaert, Mike Maillasson, Clemence Petitot, Benoit Roubinet, Blanka Didak, Ludovic Landemarre, Clarisse Bridot, Ralf Blossey, David Deniaud, Xibo Yan, Julien Bernard, Charles Tellier, Cyrille Grandjean, Franck Daligault, Sebastien G. Gouin
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Review
Chemistry, Multidisciplinary
Dimitri Alvarez Dorta, David Deniaud, Mathieu Mevel, Sebastien G. Gouin
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Biochemical Research Methods
Alejandro J. Cagnoni, Emiliano D. Primo, Sebastian Klinke, Maria E. Cano, Walter Giordano, Karina V. Marino, Jose Kovensky, Fernando A. Goldbaum, Maria Laura Uhrig, Lisandro H. Otero
ACTA CRYSTALLOGRAPHICA SECTION D-STRUCTURAL BIOLOGY
(2020)
Article
Chemistry, Physical
Jamal El-Abid, Vincent Moreau, Jose Kovensky, Vincent Chagnault
Summary: The tosylation reaction of oligosaccharides with improved regioselectivity using cobalt II chloride as a catalyst has been developed, showing good adaptability on various sugars.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Chemistry, Multidisciplinary
Matthieu Pelingre, Meriem Smadhi, Abed Bil, Veronique Bonnet, Jose Kovensky
Summary: Pure difunctionalized oligomaltosides were synthesized from perbenzoylated cyclodextrin through one-pot chemical reaction, with yields ranging from 12% to 48%.
Article
Biochemistry & Molecular Biology
Tawut Rudtanatip, Somsuda Somintara, Waraporn Sakaew, Jamal El-Abid, Maria Emilia Cano, Kamonwan Jongsomchai, Kanokpan Wongprasert, Jose Kovensky
Summary: Sulfated galactans (SG) isolated from Gracilaria fisheri were partially degraded and subsequently supplemented with octanoyl and sulfate groups. The modified SG, DSGO, exhibited the highest wound healing activity in vitro, promoting proliferation and migration of fibroblasts. This activity was confirmed in a rat excision wound model, suggesting that DSGO can enhance wound closure, re-epithelialization, and collagen arrangement, while reducing inflammation at the wound site. These findings highlight the potential of octanoyl-supplemented degraded SG for promoting wound healing.
MACROMOLECULAR BIOSCIENCE
(2022)
Article
Biochemistry & Molecular Biology
Cleiment Gonnot, Mathieu Scalabrini, Benoit Roubinet, Ceilia Ziane, Fabien Boeda, David Deniaud, Ludovic Landemarre, Seibastien G. Gouin, Laurent Fontaine, Veironique Montembault
Summary: Well-defined, highly reactive poly(norbornenyl azlactone)s were synthesized by ring-opening metathesis polymerization (ROMP) of pure exo-norbornenyl azlactone with controlled length. Postpolymerization modification (PPM) strategy based on click aminolysis of azlactone side groups was employed to convert them into glycopolymers using pegylated mannoside, heptyl-mannoside, and pegylated glucoside. The resulting glycopolymers showed strong binding inhibition against lectins, surpassing the inhibitory potential of their monovalent analogues by four to five orders of magnitude.
Article
Chemistry, Organic
D. S-E Koffi Teki, B. Coulibaly, A. Bil, A. Vallin, D. Lesur, B. Fante, V Chagnault, J. Kovensky
Summary: This study focuses on the synthesis of simple analogs of heparan sulfate (HS) to study the relationship between their structure and activity, aiming to modulate various biological processes. The development of a new synthetic method for sulfated S-disaccharide and its oxygenated analogs (O-disaccharide and sulfated O-disaccharide) was reported. The compounds were also tested for their ability to inhibit heparanase, an enzyme involved in tumor growth and inflammation, and showed significant impact of the interglycosidic sulfur atom and the 6-sulfate group.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Sebastien Depienne, Dimitri Alvarez-Dorta, Mikael Croyal, Ranil C. T. Temgoua, Cathy Charlier, David Deniaud, Mathieu Mevel, Mohammed Boujtita, Sebastien G. Gouin
Summary: This study evaluated the limitations, benefits, and relative efficiencies of eY-click conjugations using PhUr, NMePhUr, and NMeLum derivatives. NMeLum demonstrated high efficiency and complete Y-chemoselectivity on polypeptides and biologically relevant proteins after soft electrochemical activation. Side reactions on nucleophilic or heteroaromatic amino acids were never observed during mass spectrometry analysis.
Article
Chemistry, Organic
Rachid Naitaleb, Agnes Denys, Fabrice Allain, Jerome Ausseil, Sylvestre Toumieux, Jose Kovensky
Summary: The study designed and synthesized sulfated compounds capable of crossing the blood-brain barrier, which were tested on HEK-TLR4 cells, demonstrating the potential of small oligosaccharides to modulate TLR4 activity with the 6-sulfate groups playing a key role in triggering TLR4 signalization.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Christophe Dussouy, Pierre-Alban Lalys, Aurore Cabanettes, Victor Lehot, David Deniaud, Emilie Gillon, Viviane Balloy, Annabelle Varrot, Sebastien G. Gouin
Summary: In this study, potent FleA antagonists were developed based on optimized and non-hydrolysable thiofucoside ligands. Through synthesis and crystallographic analysis, a compound with significantly enhanced binding affinity was obtained, which can be used to explore the role of FleA in the infection process.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Review
Biotechnology & Applied Microbiology
Maria Emilia Cano, Alberto Garcia-Martin, Pablo Morales, Mateusz Wojtusik, Victoria E. Santos, Jose Kovensky, Miguel Ladero
FERMENTATION-BASEL
(2020)
Article
Chemistry, Multidisciplinary
Mathieu Mevel, Mohammed Bouzelha, Aurelien Leray, Simon Pacouret, Mickael Guilbaud, Magalie Penaud-Budloo, Dimitri Alvarez-Dorta, Laurence Dubreil, Sebastien G. Gouin, Jean Philippe Combal, Mirja Hommel, Gloria Gonzalez-Aseguinolaza, Veronique Blouin, Philippe Moullier, Oumeya Adjali, David Deniaud, Eduard Ayuso
Article
Chemistry, Multidisciplinary
Madeleine Cauwel, Adeline Sivignon, Clarisse Bridot, Medy C. Nongbe, David Deniaud, Benoit Roubinet, Ludovic Landemarre, Francois-Xavier Felpin, Julie Bouckaert, Nicolas Barnich, Sebastien G. Gouin
CHEMICAL COMMUNICATIONS
(2019)
