Article
Chemistry, Organic
Fengbiao Luo, Hao Dong, Weiwu Ren, Yang Wang
Summary: In this study, the first catalytic asymmetric cycloannulation of ortho-aminophenyl p-QMs was developed for the construction of tetrahydroquinolines containing three contiguous stereogenic centers. The reaction exhibited excellent functional group tolerance and high enantioselectivity, resulting in excellent yields and exclusive diastereoselectivities.
Article
Chemistry, Organic
Kyeong Seop Kim, Dae Young Kim
Summary: Chiral 3,4-dihydrocoumarin derivatives were synthesized in moderate to high yields with excellent enantioselectivity (up to 96% ee) via a one-pot cascade reaction using a binaphthyl-modified squaramide bifunctional organocatalyst. The reaction involved C-H oxidation and cyclization of 2-benzyl phenols and oxazolones under mild conditions.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Casper L. Barlose, Niklas L. ostergaard, Rene S. Bitsch, Marc V. Iversen, Karl Anker Jorgensen
Summary: An enantioselective methodology for constructing trans-Diels-Alder scaffolds with up to five contiguous stereocenters is presented, utilizing a halogen effect and a novel discovered pseudo-halogen effect. The reaction involves an endo-selective, secondary-amine catalyzed Diels-Alder reaction followed by a subsequent S(N)2-like reaction at a tertiary center to obtain the trans-Diels-Alder scaffold. The mechanism was supported by experimental results and computational studies.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Justyna Kowalska, Beata Lukasik, Sebastian Frankowski, Leslaw Sieron, Lukasz Albrecht
Summary: This paper demonstrates the application of organocatalysis in the synthesis of 2,3-dihydro-1H-pyrrolizines. The formal (3+2)-cycloaddition of alpha,beta-unsaturated aldehydes and pyrrole-based hydrazone was achieved through aminocatalytic iminium ion activation, resulting in products with high chemical yields and excellent stereocontrol. The developed method was also utilized in the first organocatalytic synthesis of the non-steroidal anti-inflammatory drug ketorolac.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Alessandro Bismuto, Patrick Mueller, Patrick Finkelstein, Nils Trapp, Gunnar Jeschke, Bill Morandi
Summary: This study presents a simple and general route to access a variety of Ni(I)-phenolate complexes, offering exciting opportunities for the discovery of new stoichiometric and catalytic reactivity, as well as the mechanistic elucidation of Ni-based catalytic cycles.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Review
Medicine, Research & Experimental
Rong Ma, Danni Lu, Jian Wang, Qian Xie, Jialiang Guo
Summary: The purpose of this study was to clarify differences in the biological activity, safety, and structure-activity relationship of the three kinds of borneol. The results showed that L-borneol has better potential in cerebrovascular diseases, the three kinds of borneol have stronger penetration-promoting effects on hydrophilic drugs, L-borneol and isoborneol promote intestinal mucosal absorption of drugs via bidirectional regulation of P-glycoprotein, D-borneol exhibits better antitumour sensitizing effects than L-borneol, L-borneol exhibits better inhibition of bacterial adhesion because of its C2 chiral centre, and synthetic borneol is less safe. Therefore, L-borneol has excellent potential in many aspects and can effectively replace expensive D-borneol in some applications.
BIOMEDICINE & PHARMACOTHERAPY
(2023)
Article
Biochemistry & Molecular Biology
Mary C. C. Hennessy, Hirenkumar Gandhi, Timothy P. P. O'Sullivan
Summary: A methodology for synthesizing γ, δ-unsaturated β-keto esters through asymmetric peroxidation is described. The cinchona-derived organocatalyst allows for high enantioselectivity (up to 95:5) in obtaining the desired γ-peroxy-β-keto esters. Furthermore, the resulting δ-peroxy esters can be easily reduced to chiral δ-hydroxy-β-keto esters without affecting the functionality of the β-keto ester. Importantly, this chemistry provides a concise route to chiral 1,2-dioxolanes, a common motif in bioactive natural products, via a novel P2O5-mediated cyclization of the corresponding δ-peroxy-β-hydroxy esters.
Article
Engineering, Environmental
Zhihao Sun, Zhaoqian Yan, Zihao Guo, Hongshou Liu, Lanling Zhao, Lei Qian
Summary: Derivatized multi-void composite microplates (CoNXC) with high-efficient electromagnetic wave absorption (EMA) were successfully fabricated using a two-step pyrolysis process assisted by molten dual-salt-mediated template. N-doping modulated the bonding configurations of Co/N atoms, enhancing dielectric loss capacity. CoNXC exhibited high EMA performance even with high filler loading and outperformed most reported derivatized carbon-based composites.
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Chemistry, Organic
Kavnen Tseke, Claire Lennon, Joseph O'Mahony, Michael Kinsella
Summary: The efficient L-leucinol catalyzed asymmetric synthesis of 3-substitued-3-hydroxyoxindoles was successfully carried out for the first time under continuous flow, utilizing neat acetone as the optimal solvent. The reaction could be accelerated at higher temperatures without affecting enantioselectivity, demonstrating a safer and more efficient method for this type of synthesis.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Editorial Material
Oncology
Lisa M. Cordes, Fatima Karzai, William D. Figg, Ravi A. Madan
Summary: Androgen deprivation therapy (ADT) is an important treatment modality for prostate cancer. Relugolix, the only ADT option via an oral route approved by the FDA in 2020, provides some advantages but requires a balanced discussion to understand its true benefits compared to long-acting injectable formulations of ADT in different clinical settings. Factors such as patient preference, compliance, financial toxicity, and pharmacologic characteristics need to be considered. This commentary explores the role of relugolix in the treatment of prostate cancer.
Article
Physics, Multidisciplinary
Matthew J. Trott, Chris A. Hooley
Summary: By analyzing the electron-electron interactions and Fermi surface nesting in monolayers of vanadium diselenide, the authors demonstrate the competitive mechanism between charge density-wave and superconducting states.
COMMUNICATIONS PHYSICS
(2021)
Article
Chemistry, Applied
Yu-Shi Jiang, Feng Liang, Ai-Min Chen, Shan-Shan Li, Xue-Ling Luo, Peng-Ju Xia
Summary: Functionalized dihydrocoumarins, including 3-amino- and 4-amino dihydrocoumarins serving as alpha- and beta-amino acid derivatives, have been synthesized using one-step site- and regioselective alkylamination from coumarins. This conversion offers 35 examples in 24% to 81% yields.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Polymer Science
Andrea H. Westlie, Sarah A. Hesse, Xiaoyan Tang, Ethan C. Quinn, Celine R. Parker, Christopher J. Takacs, Christopher J. Tassone, Eugene Y. -X. Chen
Summary: This study presents a stereoselective-chemocatalytic route for the production of discrete hard-soft-hard all-PHA tri-block copolymers. These copolymers exhibit high molar mass, low dispersity, and tunable mechanical properties. This research is of great significance for the preparation of biodegradable polymers.
Article
Chemistry, Organic
Pragya Sharma, Sanjay Singh, Chinmoy Kumar Hazra
Summary: The facile and efficient synthesis of a unique class of 4-aryl-hydrocoumarins with various applications in medicinal chemistry and natural products is reported. The authors have developed a Bronsted acid-catalyzed, multicomponent, one-pot approach for producing 4-aryl-coumarin derivatives. The practicality of this method is demonstrated through the synthesis of bioactive compounds, late-stage functionalization of natural products, and gram-scale synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jing-Xiang Xu, Kai-Ti Chu, Ming-Hsi Chiang, Jeng-Liang Han
Summary: A direct catalytic asymmetric functionalization of 2-methylindoles using organocatalysis was described. An efficient asymmetric allylic alkylation reaction with chiral biscinchona alkaloid catalyst provided functionalized indole derivatives in good yields and enantioselectivities.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Helma Wennemers
Summary: This article summarizes recent research highlights in the areas of asymmetric catalysis, supramolecular chemistry, and chemical biology, focusing on the development of bioinspired peptide catalysts, synthetic collagen peptides, supramolecular porous assemblies, and cell-penetrating peptides.
Article
Chemistry, Multidisciplinary
Greta Vastakaite, Claudio E. Grunenfelder, Helma Wennemers
Summary: This study presents a tripeptide catalyst for the efficient and stereoselective synthesis of chiral succinimides via conjugate addition reactions between aldehydes and C-substituted maleimides. The catalyst exhibits high chemoselectivity and allows direct derivatization of the succinimides to access other chiral compounds.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Applied
Jasper S. Moehler, Lena K. Beiersdoerfer, Brenno Masina, Philipp Wechsler, Helma Wennemers
Summary: N-heterocyclic moieties are commonly found in pharmaceuticals and agrochemicals, but pose a challenge for metalorganic and organocatalytic transformations. This study presents tripeptide catalysts for stereoselective conjugate addition reactions between N-heterocyclic substituted aldehydes and electrophiles, achieving high yields and selectivities.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Tomas Fiala, Emilia P. Barros, Marc-Olivier Ebert, Enrico Ruijsenaars, Sereina Riniker, Helma Wennemers
Summary: This study reveals the significant impact of terminal residues on the stability of collagen model peptides (CMPs). By combining various experimental and simulation techniques, the researchers demonstrate how peptide termini preorganize into a polyproline-II helical structure and affect the stability of triple helices. These findings have important implications for designing peptide mimics of structural proteins and provide a straightforward method to tune the stability of CMPs for various applications.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Tomas Fiala, Emilia P. Barros, Rahel Heeb, Sereina Riniker, Helma Wennemers
Summary: This study elucidates the impact of frame, terminal functional group, and charge on the stability of collagen triple helices, and proposes a method for predicting the melting temperatures of CMP trimers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Rebecca J. B. Schaefer, Kayla Wilson, Maurice Biedermann, Bradley S. Moore, Simon Sieber, Helma Wennemers
Summary: This study successfully detected and isolated microgram quantities of isonitrile compounds using the isonitrile-chlorooxime ligation system and a reactivity-based screening protocol.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Physical
Bartosz Lewandowski, Rebecca J. B. Schafer, Etienne Cotter, Dora Harangozo, Helma Wennemers
Summary: Templated synthesis is a fascinating strategy for controlling the length of oligomer synthesis. Traditionally, this requires stoichiometric amounts of the template. However, this article presents an innovative approach using catalytic macrocyclic templates that achieve remarkable length control. The authors also discuss their efforts in developing linear templates for catalytic length-controlled oligomer synthesis.
FARADAY DISCUSSIONS
(2023)
Article
Biochemistry & Molecular Biology
Tobias Schnitzer, Nils Trapp, Lisa-Marie Fischer, Helma Wennemers
Summary: Crystal structures of N-acetylated proline and its analogs with four- and six-membered rings were compared, showing distinct conformational differences that contribute to the zigzag lattice structure.
JOURNAL OF PEPTIDE SCIENCE
(2023)
Article
Chemistry, Organic
Rudiger Bormann, Dominik Zetschok, Helma Wennemers
Summary: Chlorinated malonic acid half thioesters were used as surrogates for chloroacetates in organocatalyzed decarboxylative aldol-type additions, leading to enantioenriched alpha-chloro-beta-hydroxy thioesters. The obtained compounds could be further derivatized, as demonstrated in the synthesis of (+)-prebalamide and (+)-norbalasubramide analogs.
Article
Chemistry, Multidisciplinary
Alena Budinska, Helma Wennemers
Summary: This article presents a mild and efficient organocatalytic method for the stereoselective synthesis of chiral triflones using alpha-aryl vinyl triflones, previously unexplored in asymmetric synthesis. The products can be easily derivatized into disubstituted delta-sultones, gamma-lactones, and pyrrolidine heterocycles, highlighting their synthetic versatility.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Biochemistry & Molecular Biology
Tomas Fiala, Rahel Heeb, Luca Vigliotti, Helma Wennemers
Summary: N-terminal acylation is commonly used to install functional moieties on collagen model peptides. The length of short acyl capping groups has different effects on the thermal stability of collagen triple helices in different frames. This study provides a basis for designing N-terminally functionalized CMPs with predictable effects on triple helix stability.
Article
Chemistry, Multidisciplinary
Giuseppe Antoniazzi, Rebecca J. B. Schafer, Maurice Biedermann, Eric Ruttimann, Helma Wennemers
Summary: This study introduces (4S)- and (4R)-isonitrileproline as building blocks for solid-phase peptide synthesis and investigates the stereoelectronic effect of isonitrile group. The results demonstrate the potential value of Inp in peptide derivatization.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Sonia Vela-Gallego, Bartosz Lewandowski, Jasper Moehler, Alonso Puente, David Gil-Cantero, Helma Wennemers, Andres de la Escosura
Summary: This study investigates the control and tuning of properties of biohybrid catalysts through self-assembly. By combining catalytic tripeptide, fatty acid, and nucleobase derivatives, the biohybrid catalysts form fibrillar structures and catalyze specific reactions in aqueous media. The interactions between nucleobases enhance the ordering of supramolecular structures and affect the catalytic activity and selectivity.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Athanasios Markos, Maurice Biedermann, Johannes Heimgartner, Adeline Schmitt, Kathrin Lang, Helma Wennemers
Summary: In this study, C,N-cyclic-N'-acyl azomethine imines (AMIs) were introduced to bioorthogonal reactions in an aqueous environment, showing stability under physiological conditions and selective reactivity with isonitriles. The AMI-isonitrile ligation demonstrated biocompatibility and orthogonality to commonly used bioorthogonal reactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Tobias Schnitzer, Jonas W. Rackl, Helma Wennemers
Summary: This study investigated the properties of tripeptide catalysts in complex mixtures and achieved high reactivity and stereoselectivity by tailoring the conformation of tripeptides. The tripeptide catalysts exhibited remarkable chemoselectivity, even catalyzing reactions in cell lysates.
