Review
Biochemistry & Molecular Biology
Olga Bakulina, Anna Inyutina, Dmitry Dar'in, Mikhail Krasavin
Summary: This review summarizes recent developments in multicomponent reactions of diazo compounds, analyzing the role of diazo reagents and the type of interaction between components. In contrast to previous reviews mostly focused on metal catalyzed transformations, this work covers a substantial amount of organocatalytic or catalyst-free methodologies.
Article
Biochemical Research Methods
Ningning Zhang, Changzhu Wu
Summary: This study proposes an advanced artificial enzyme by polymeric modularity as an efficient aldolase mimic for aqueous asymmetric aldol reactions. The tailored conjugates exhibited remarkable catalytic performance and excellent selectivity. Additionally, the artificial enzyme showed high tolerance and reusability.
ACS SYNTHETIC BIOLOGY
(2022)
Review
Chemistry, Organic
Raghunath Chowdhury, Akhil K. Dubey, Mario Waser
Summary: Asymmetric decarboxylative aldol reactions of MAHTs, MAHOs, and beta-ketoacids with different carbonyl compounds are valuable transformations for the direct synthesis of enantio-enriched beta-hydroxy esters and ketones. Organocatalysis and metal catalysis are the leading strategies for carrying out these reactions in recent progress.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Nikita Das, Chandan Maity
Summary: In living organisms, enzyme catalysis in aqueous media has precise spatiotemporal control. This knowledge has inspired the design of biomimetic artificial catalysts. However, it is challenging for these catalysts to be effective in natural-like environments. Control over reaction rate and selectivity can be achieved by incorporating stimuli-responsive features into smart catalytic systems. This review summarizes switchable catalytic systems that operate in aqueous environments in response to external stimuli, providing new opportunities for the development of smart materials for biomedicine and chemical biology.
COMMUNICATIONS CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Stuart C. D. Kennington, Saul F. Teloxa, Miguel Mellado-Hidalgo, Oriol Galeote, Sabrina Puddu, Marina Bellido, Pedro Romea, Felix Urpi, Gabriel Aullon, Merce Font-Bardia
Summary: A direct and asymmetric aldol reaction of N-acyl thiazinanethiones with aromatic aldehydes catalyzed by chiral nickel(II) complexes was reported. The reaction gives high yields of O-TIPS-protected anti-aldol adducts with remarkable stereocontrol and atom economy. The removal of the achiral scaffold provides enantiomerically pure intermediates with synthetic interest for producing anti-alpha-amino-beta-hydroxy and alpha,beta-dihydroxy carboxylic derivatives, with theoretical calculations explaining the observed high stereocontrol.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Yujiro Hayashi
Summary: The aldol reaction is a significant carbon-carbon bond-forming reaction in organic chemistry. The use of trifluoromethyl-substituted diarylprolinol as an organocatalyst has been found to be effective in promoting cross-aldol reactions with excellent selectivities.
Review
Chemistry, Multidisciplinary
Yong Xia, Xiaohua Liu, Xiaoming Feng
Summary: The donor-acceptor (D-A) cyclopropanes, due to the synergistic push-pull effect of vicinal electron-donating and electron-withdrawing groups, are recognized as powerful building blocks for generating polyfunctional reactive intermediates. Enantioselective reactions of D-A cyclopropanes provide an efficient approach to enantioenriched acyclic and cyclic compounds. Chiral Lewis/Bronsted acids, transition metals, and organocatalysts have been designed for such transformations, including ring-openings, annulations, and rearrangements.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Yuvraj Garg, James Osborne, Serhii Vasylevskyi, Nivedha Velmurugan, Fujie Tanaka
Summary: 1,3-Diamine-derived catalysts were synthesized and utilized in asymmetric Mannich reactions of ketones. The Mannich products with high enantioselectivities were obtained under mild conditions through catalysis by one of the 1,3-diamine derivatives in the presence of acids. Bond formation primarily occurred at the less-substituted α-position of the ketone carbonyl group. The primary and tertiary amines of the 1,3-diamine derivative cooperatively acted for the catalysis.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Engineering, Environmental
Celine Demeese, Clara Lods, David-Alexandre Buisson, Edmond Gravel, Irishi N. N. Namboothiri, Eric Doris
Summary: A proline analog assembled on carbon nanotubes was utilized as a heterogenized catalyst in asymmetric aldol reactions, showing high efficiency, good enantioselectivity, and sustainability using pure water as the solvent. The catalyst operates with low loadings and can be recycled without loss of performance, resulting in aldol products with yields up to 99% and enantiomeric excesses up to 98%.
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Chemistry, Organic
Hyoung Min Yeo, Sungmin Kang, Taek Hyeon Kim
Summary: The first chiral proline amide-isothiouronium based bifunctional organocatalyst was developed, showing high to quantitative yields in aldol products with excellent control performance of diastereoselectivities and enantioselectivity.
TETRAHEDRON LETTERS
(2021)
Review
Chemistry, Applied
Sara Meninno, Francesca Franco, Maurizio Benaglia, Alessandra Lattanzi
Summary: Pyrazoleamides have gained attention as reactive and practical surrogates in asymmetric catalysis, particularly in a variety of metal- and organocatalytic transformations. Their relevance has extended to photoredox catalysis and challenging stereoselective bond-forming reactions in recent years.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Kazuhiro Nagata, Chihiro Nakagawa, Wakana Yokoyama, Haruka Usui, Rikako Mochizuki, Takuya Kanemitsu, Michiko Miyazaki, Takashi Itoh
Summary: The catalytic activities of 3-decyl-beta-proline in Michael addition using water as the solvent were investigated, showing that the decyl substituent promoted the reaction through hydrophobic interactions to afford high yield and high diastereoselectivity under low catalyst loading.
Article
Chemistry, Multidisciplinary
Vibha V. Kanale, Christopher Uyeda
Summary: Cobalt catalysts facilitate highly enantioselective ring-opening reactions of 2,5-dihydrofurans using vinylidenes. The resulting products are acyclic organozinc compounds, capable of further functionalization with an electrophile. The proposed mechanism involves the formation of a cobalt vinylidene species that adds to the alkene via a [2+2]-cycloaddition pathway, followed by ring-opening through outer-sphere & beta;-O elimination assisted by a ZnX2 Lewis acid. DFT models explain the observed stereochemical outcome by suppressing competing inner-sphere syn & beta;-H and & beta;-O elimination pathways due to the geometric constraints of the metallacycle intermediate. Cobalt catalysts also promote enantioselective ring-opening reactions of unstrained heterocycles via reductive addition of 1,1-dichloroalkenes. The resulting products are acyclic homoallylic alcohols with a vinylzinc motif, which can be further modified with an electrophile. Mechanistic studies suggest that the ring-opening occurs through outer-sphere & beta;-O elimination facilitated by a Zn(II) Lewis acid.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Physical
Nilanjana Majumdar
Summary: Catalytic asymmetric transformation is a powerful strategy for synthesizing diverse nonracemic molecular entities. Carboxylic acids have been explored as building blocks in this area, and significant advancements have been made in the last three decades. They can act as both C- and O-nucleophiles, as well as electrophiles, in asymmetric reactions under catalytic conditions.
Review
Chemistry, Multidisciplinary
Jian Luo, Guo-Shu Chen, Shu-Jie Chen, Zhao-Dong Li, Yun-Lin Liu
Summary: This review discusses the recent advancements in catalytic enantioselective isocyanide-based reactions, highlighting the advantages, limitations, possible mechanisms, and synthetic applications of each reaction type. Additionally, it provides a personal outlook on potential opportunities for further exploration in this rapidly growing field.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Correction
Chemistry, Multidisciplinary
Artur Swierczek, Krzysztof Pociecha, Marietta Slusarczyk, Grazyna Chlon-Rzepa, Sebastian Bas, Jacek Mlynarski, Krzysztof Wieckowski, Monika Zadrozna, Barbara Nowak, Elzbieta Wyska
PHARMACEUTICAL RESEARCH
(2020)
Article
Chemistry, Multidisciplinary
Ewa P. Gajewska, Sara Szymkuc, Piotr Dittwald, Michal Startek, Oskar Popik, Jacek Mlynarski, Bartosz A. Grzybowski
Article
Chemistry, Organic
Matylda Stefaniak, Szymon Buda, Jacek Mlynarski
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Physical
Sebastian Bas, Yasuhiro Yamashita, Shu Kobayashi
Article
Chemistry, Multidisciplinary
Monika Pasternak-Suder, Wojciech Pacult, Sebastian Bas, Jacek Mlynarski
Article
Chemistry, Applied
Izabela Weglarz, Karol Michalak, Jacek Mlynarski
Summary: The study reported the first successful enantioselective hydrosilylation of cyclic imines promoted by a chiral zinc complex, achieving pharmaceutically relevant enantioenriched 2-aryl-substituted pyrrolidines with excellent enantioselectivities. The synthetic utility of the presented methodology was demonstrated in an efficient synthesis of pharmaceutical drug precursors to Aticaprant and Larotrectinib.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Spectroscopy
Ewelina Matuszyk, Adriana Adamczyk, Basseem Radwan, Anna Pieczara, Piotr Szczesniak, Jacek Mlynarski, Katarzyna Kaminska, Malgorzata Baranska
Summary: Raman imaging with molecular reporters is a novel method for subcellular visualization, offering improved selectivity and sensitivity; this study aimed to visualize organelles in endothelial cells using established and new reporters, and to investigate changes in organelle distribution after induced dysfunction, highlighting drawbacks of established reporters.
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
(2021)
Article
Chemistry, Applied
Joanna A. Jaszczewska-Adamczak, Jacek Mlynarski
Summary: Utilizing chiral dinuclear magnesium complexes for epoxidation reactions allows for efficient and highly selective synthesis of enantioenriched oxiranes, providing a new possibility for asymmetric synthesis.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Biochemistry & Molecular Biology
Roberto Campagna, Lukasz Mateuszuk, Kamila Wojnar-Lason, Patrycja Kaczara, Anna Tworzydlo, Agnieszka Kij, Robert Bujok, Jacek Mlynarski, Yu Wang, Davide Sartini, Monica Emanuelli, Stefan Chlopicki
Summary: Nicotinamide N-methyltransferase (NNMT) plays an important role in endothelial cells by regulating cell viability, possibly through the modulation of SIRT1 expression levels under oxidative stress insult.
BIOCHIMICA ET BIOPHYSICA ACTA-MOLECULAR CELL RESEARCH
(2021)
Article
Chemistry, Organic
Robert Pawlowski, Maciej Stodulski, Jacek Mlynarski
Summary: This study presents an efficient catalytic propargylation of CoQ0 using the cooperative effect of Sc(OTf)(3) and Hantzsch ester. A broad range of propargylic alcohols can be converted into CoQ0 derivatives containing triple bonds in good to excellent yields. The mechanism involving hydroquinone and dimeric propargylic moiety intermediates is discussed.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biophysics
Basseem Radwan, Stefano Rocchetti, Ewelina Matuszyk, Magdalena Sternak, Maciej Stodulski, Robert Pawlowski, Jacek Mlynarski, Krzysztof Brzozowski, Stefan Chlopicki, Malgorzata Baranska
Summary: This study introduces a Raman-based imaging method using EdU as a probe to track endothelial cell proliferation, providing an alternative to fluorescence-based assays for assessing endothelial proliferation and regeneration.
BIOSENSORS & BIOELECTRONICS
(2022)
Article
Chemistry, Inorganic & Nuclear
Katarzyna Rogacz, Maria Brzozowska, Sebastian Bas, Katarzyna Kurpiewska, Dawid Pinkowicz
Summary: This study explores the structures and magnetic properties of photo-responsive magnets that can be controlled by visible light irradiation. The authors present two erbium(III)-based coordination systems, one trinuclear molecule and one 1D coordination chain, both showing slow dynamics of magnetization. The trinuclear compound exhibits immediate color change in response to near-UV irradiation, while the chain-like compound does not show significant signs of photoisomerization.
INORGANIC CHEMISTRY
(2022)
Article
Spectroscopy
Anna Pieczara, Ewelina Matuszyk, Piotr Szczesniak, Jacek Mlynarski, Malgorzata Baranska
Summary: The role of mitochondria in cellular function, including the production of reactive oxygen species and the regulation of cell death, is significant. This study utilizes Raman microscopy to locate and track functional changes in mitochondria, and explores the potential of using Raman probes for cell labeling to improve specificity and sensitivity.
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
(2023)
Article
Biophysics
Anna Pieczara, Aleksandra Borek-Dorosz, Szymon Buda, William Tipping, Duncan Graham, Robert Pawlowski, Jacek Mlynarski, Malgorzata Baranska
Summary: This study uses a Raman probe, 3-OPG, to track metabolic changes in endothelial cells. The results show that 3-OPG is a sensitive sensor for studying glucose metabolism and its changes in cellular inflammation. This research is important for understanding the role of endothelial cell metabolism in disease development.
BIOSENSORS & BIOELECTRONICS
(2023)
Article
Chemistry, Organic
Daniel Kamzol, Maxime Neuville, Chloe Cocaud, Killian Tiger, Baptiste Taffoureau, Krzysztof Lewinski, Justyna Jaszczyk, Olivier R. Martin, Sebastian Bas, Sylvain Routier, Isabelle Gillaizeau, Frederic Buron, Cyril Nicolas
Summary: This study comprehensively investigates the preparation and reactivity of N-tert-butanesulfinyl glycosylamines with simple Grignard and organo lithium reagents in batch and continuous flow chemistry. These carbohydrate derivatives, acting as latent imine equivalents, react readily with various carbon nucleophiles, making them useful precursors for the diastereoselective synthesis of bioactive compounds such as iminosugar-C-glycosides. Additionally, a hybrid protocol combining flow addition of benzylmagnesium chloride to a (S-R)-arabinofuranosylamine substrate at room temperature with a batch cyclization protocol is introduced for the first time. Notably, this semi-continuous flow process shortens the synthesis of imino-C-glycoside scaffolds to a single workday.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Yikuan Liu, Xiaona Liu, An Su, Chengtao Gong, Shenwei Chen, Liwei Xia, Chengwei Zhang, Xiaohuan Tao, Yue Li, Yonghe Li, Tulai Sun, Mengru Bu, Wei Shao, Jia Zhao, Xiaonian Li, Yongwu Peng, Peng Guo, Yu Han, Yihan Zhu
Summary: Covalent organic frameworks are crystalline porous materials with designable structures and functions, which can acquire multifunctionalities and have versatile applications in gas separation/storage, catalysis, and optoelectronic devices.
CHEMICAL SOCIETY REVIEWS
(2024)
Review
Chemistry, Multidisciplinary
Heyang Zhang, Jo Vandesompele, Kevin Braeckmans, Stefaan C. De Smedt, Katrien Remaut
Summary: Gene therapy has the potential to revolutionize the treatment of inherited and acquired diseases, but its success rate is currently limited. This review focuses on the obstacles faced by gene therapies in the human body, such as nucleic acid degradation by abundant nucleases, and discusses strategies to reduce degradation and methods to assess nucleic acid integrity.
CHEMICAL SOCIETY REVIEWS
(2024)
Review
Chemistry, Multidisciplinary
Chenxi Duan, Chunming Cui
Summary: Low valent group 14 compounds with diazaborolyl substituents exhibit unique structures and reactivity due to the combination of sigma-electron donation and steric hindrance. The modulation of the HOMO-LUMO gap by the diazaborolyl substituents results in novel reaction patterns in the activation of small molecules and inert chemical bonds.
CHEMICAL SOCIETY REVIEWS
(2024)
Review
Chemistry, Multidisciplinary
David E. Salazar Marcano, Nada D. Savic, Kilian Declerck, Shorok A. M. Abdelhameed, Tatjana N. Parac-Vogt
Summary: Metal-oxo clusters have great potential in various fields and can react with biomolecules, making them promising for applications in disease treatment and energy development. They can also be used in the development of inorganic drugs and bioanalytical tools.
CHEMICAL SOCIETY REVIEWS
(2024)
Review
Chemistry, Multidisciplinary
Lana K. Moree, Logan A. V. Faulkner, James D. Crowley
Summary: In this tutorial review, the general methods for synthesizing heterometallic metallosupramolecular architectures (MSAs), specifically heterometallic cages, are examined. The intrinsic properties and potential applications of these cages as host-guest systems and reaction catalysts are discussed.
CHEMICAL SOCIETY REVIEWS
(2024)
