Review
Chemistry, Multidisciplinary
Yang Zhang, Michal Szostak
Summary: Total synthesis is the perfect combination of art and science, and C-H functionalization provides a powerful platform for rapid synthesis of complex natural products and changes the design of retrosynthetic strategies, leading to natural product scaffolds with enhanced biological activities.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Applied
Amalia-Sofia Piticari, Daniele Antermite, Joe Higham, J. Harry Moore, Matthew P. Webster, James A. Bull
Summary: This study achieved the selective Pd-catalyzed C-H cis-functionalization of piperidine and tetrahydropyran carboxylic acids using a C(4) aminoquinoline amide auxiliary. High mono- and cis-selectivity was obtained by adding mesityl carboxylic acid. The reaction conditions developed in this study had significantly lower temperatures compared to other reported heterocycle C(sp(3))-H functionalization reactions, and a one-pot C-H functionalization-epimerization procedure was established to directly obtain the trans-3,4-disubstituted isomers. Diverse aminoquinoline removals were achieved by installing carboxylic acid, alcohol, amide, and nitrile functional groups. Overall, fragment compounds suitable for screening were synthesized in 3-4 steps from readily-available heterocyclic carboxylic acids.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Mohammed Sharique, Jadab Majhi, Roshan K. Dhungana, Lisa Marie Kammer, Matthias Krumb, Alexander Lipp, Eugenie Romero, Gary A. Molander
Summary: In this study, a simple, open-air, and efficient light-mediated Minisci C-H alkylation method is described, which is based on the formation of an electron donor-acceptor complex. Unlike previous protocols, this method does not require a photocatalyst, single electron transfer agent, or oxidant additive. The reaction can proceed under mildly acidic and open-air conditions, and it yields moderate to good amounts of Minisci alkylation products.
Article
Chemistry, Multidisciplinary
Soojun Park, Jiwoo Lee, Jae Hyun Kim, Yeji Jeong, Seokwoo Lee, Su Won Lee, Sanghee Kim
Summary: A concise total synthesis of salinosporamides and cinnabaramides was achieved through the combined use of memory of chirality and dynamic kinetic resolution principles, involving aldol reactions and hydrolysis reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Jie Liu, Gregor S. Cremosnik, Felix Otte, Axel Pahl, Sonja Sievers, Carsten Strohmann, Herbert Waldmann
Summary: This study presents the design and synthesis of a collection of 155 pyrroquinoline pseudo-NPs, combining fragments characteristic of tetrahydroquinoline and pyrrolidine classes in novel arrangements. Cheminformatic analysis and biological evaluation revealed chemically diverse pseudo-NP classes with distinct bioactivity patterns, dependent on fragment connectivity and regioisomeric arrangement.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Nicolas Muller, Benedikt S. Schreib, Sebastian U. Leutenegger, Erick M. Carreira
Summary: In this study, the palladium-catalyzed aminoalkynylation of electronically unbiased olefins with iodoalkynes was reported. Using the picolinamide auxiliary, the syn-selective aminoalkynylation of mono-, di-, and trisubstituted alkenes was achieved, leading to the formation of corresponding pyrrolidines in high yield and single diastereomers. The picolinamide also allowed for the rapid synthesis of functionalized olefins and subsequent Pictet-Spengler reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Johannes Grosskopf, Manuel Plaza, Roger Jan Kutta, Patrick Nuernberger, Thorsten Bach
Summary: 2,5-Diketopiperazines are cyclic dipeptides with a wide range of applications, and their enantioselective preparation can be achieved through photochemical deracemization, allowing for stereochemical editing at a single position while maintaining other stereogenic centers unaffected. The chiral benzophenone catalyst in combination with irradiation at lambda=366 nm enables the establishment of configuration at the stereogenic carbon atom C6 at will.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Eric D. Gardner, Bryce P. Johnson, Dustin A. Dimas, Heather E. McClurg, Zachary C. Severance, Anthony W. Burgett, Shanteri Singh
Summary: This study explores indole-prenylating enzymes as a strategy to directly functionalize azaindole-substituted analogs of natural products. The discovery that nitrogenous indole bioisosteres can be accepted by these enzymes opens up previously unavailable chemical space in the search for bioactive indolediketopiperazine analogs.
Article
Chemistry, Multidisciplinary
Shahilan Ratnam, Shreya Unone, Daniel Janssen-Mueller
Summary: It is found that alkyl-substituted dihydroquinolines derived from 2,2'-biquinoline can serve as efficient radical precursors, forming primary, secondary, and tertiary alkyl radicals. Copper catalysis allows the hydroalkylation of benzalmalononitriles and N-Boc protected diazenes under mild conditions, with yields up to 85%. The reactivity of the dihydroquinolines towards denitrative alkylation of nitroolefins, such as β-nitrostyrene, has been discovered. Notably, the released biquinoline can be recycled, greatly improving the atom-economy of these alkyl radical precursors compared to previous N-heterocyclic electroauxiliaries.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Johannes Grosskopf, Alexandra A. Heidecker, Thorsten Bach
Summary: Racemic 3-substituted oxindoles can be converted into enantiomerically pure or enriched material through photochemical deracemization process. Light energy compensates for the loss of entropy and enables predictable editing of the stereogenic center. The obtained oxindoles are valuable intermediates for further transformations with complete retention at the stereogenic center.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Fang Wang, Qianting Zhou, Xinying Zhang, Xuesen Fan
Summary: A novel and efficient alpha-C(sp(3))-H alkenylation of cyclic amines with maleimides was presented, featuring readily available and structurally diverse substrates, a green and economical catalyst, a unique reaction pathway, mild reaction conditions, high efficiency, and excellent atom economy. This new reaction enriches the application of Fe(III)-catalyzed C(sp(3))-H activation and functionalization.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Igor Mueller, Christian Gunnar Werncke
Summary: In this study, we disclosed the easy reduction of pyridine (and its derivatives) by linear 3d metal(I) silylamides, resulting in intermolecular C-C coupling to form dinuclear metal(II) complexes. Iron was found to demonstrate reversible C-C coupling in solution, and the dinuclear metal(II) complex incorporating iron facilitated isomerization of 1,4-cyclohexadiene. Furthermore, reactions of silylamides with perfluoropyridine led to C-F bond cleavage and the formation of metal(II) fluoride complexes.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Review
Chemistry, Applied
Roman S. Malykhin, Alexey Yu Sukhorukov
Summary: The review summarizes recent advances in the synthesis of C2-halogenated nitrogen heterocycles via nucleophilic halogenation of corresponding N-oxides and its application in pharmaceutical synthesis. It provides a practical guide based on extensive literature analysis to help practitioners choose optimal reagents/conditions for nucleophilic halogenation of N-heterocycles of different types. The bibliography contains 199 references.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Yi-Ming Shi, Jan J. Crames, Laura Czech, Kenan A. J. Bozhuyuk, Yan-Ni Shi, Merle Hirschmann, Stefanie Lamberth, Peter Claus, Nicole Paczia, Christian Ruckert, Jorn Kalinowski, Gert Bange, Helge B. Bode
Summary: This study reveals the biosynthetic potential of a widespread benzobactin gene cluster and identifies the acyl AMP-ligase responsible for the last cyclization step. Genome mining of Pseudomonas chlororaphis uncovered the presence of the gene cluster in different bacterial species, highlighting the regulatory mechanisms and structural diversity of benzobactin biosynthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Jia-Xue Wu, Huai-Wei Wang, Wen-Zeng Duan, Hong-Han Ji, Jian-Min Dou, Xian-Qiang Huang, Yi Lu, Da-Cheng Li
Summary: A novel catalytic method for regioselective C-H heteroarylation/esterification of acrylic acid through carboxylate-assisted iridium (III) catalysis is reported for the first time. This method shows good compatibility with various substituted acrylic acids and heteroaromatic boronates, and the resulting product exhibits potential application for the synthesis of nitrogen-containing organic functional materials.
Article
Biotechnology & Applied Microbiology
Andrea Palyzova, Jiri Zahradnik, Helena Maresova, Lucie Sokolova, Eva Kyslikova, Michal Grulich, Vaclav Stepanek, Tomas Rezanka, Pavel Kyslik
FOLIA MICROBIOLOGICA
(2018)
Article
Plant Sciences
Lenka Prochazkova, Daniel Remias, Andreas Holzinger, Tomas Rezanka, Linda Nedbalova
EUROPEAN JOURNAL OF PHYCOLOGY
(2018)
Review
Biotechnology & Applied Microbiology
Tomas Rezanka, Andrea Palyzova, Karel Sigler
FOLIA MICROBIOLOGICA
(2018)
Article
Biochemical Research Methods
Tomas Rezanka, Irena Kolouchova, Linda Nedbalova, Karel Sigler
JOURNAL OF CHROMATOGRAPHY A
(2018)
Article
Biochemistry & Molecular Biology
Tomas Rezanka, Milada Vitova, Jaromir Lukavsky, Karel Sigler
Review
Biochemistry & Molecular Biology
Tomas Rezanka, Irena Kolouchova, Lucia Gharwalova, Andrea Palyzova, Karel Sigler
Article
Biochemistry & Molecular Biology
Tomas Rezanka, Irena Kolouchova, Lucia Gharwalova, Jana Dolezalova, Linda Nedbalova, Karel Sigler
Article
Biochemistry & Molecular Biology
Tomas Rezanka, Jaromir Lukaysky, Milada Vitova, Linda Nedbalova, Karel Sigler
Article
Biotechnology & Applied Microbiology
Andrea Palyzova, Jiri Zahradnik, Helena Maresova, Tomas Rezanka
INTERNATIONAL BIODETERIORATION & BIODEGRADATION
(2019)
Article
Biochemical Research Methods
Tomas Rezanka, Milada Vitova, Jaromir Lukavsky, Linda Nedbalova, Irena Kolouchova
JOURNAL OF CHROMATOGRAPHY A
(2019)
Article
Biochemical Research Methods
Andrea Palyzova, Tomas Rezanka
JOURNAL OF CHROMATOGRAPHY A
(2020)
Article
Biochemical Research Methods
Andrea Palyzova, Tomas Cajthaml, Tomas Rezanka
Summary: A combination of chromatographic and enzymatic methods was used to identify the molecular species of triacylglycerols from Streptomyces avermitilis. The study revealed the impact of different carbon sources and precursor-directed biosynthesis on the ratio of fatty acids, while also highlighting the importance of TAG structure in chromatographic separation.
Article
Biodiversity Conservation
Lenka Prochazkova, Daniel Remias, Andreas Holzinger, Tomas Rezanka, Linda Nedbalova
Summary: Red snow caused by spherical cysts can be found worldwide, while an orange snow phenomenon caused by spherical cells is restricted to (Sub-)Arctic climates. Comparing ecophysiologically, significant differences in fatty acid and pigment profiles were found in the two species occurring in the same localities at Svalbard, which play an important role in adaptation to extreme conditions. The reasons why S. aurantia has not been found outside (Sub-)Arctic climate types remain unknown.
Article
Biochemistry & Molecular Biology
Olga Matatkova, Irena Kolouchova, Kristyna Lokocova, Jana Michailidu, Petr Jaros, Marketa Kulisova, Tomas Rezanka, Jan Masak
Summary: The study found that the biological activity of rhamnolipids depends on their properties and the conditions of biofilm formation. Measurement and monitoring of biofilm growth and eradication under static and dynamic conditions are crucial for understanding biofilm behavior.
Article
Chemistry, Multidisciplinary
Richard Jezdik, Marketa Koukalova, Olga Matatkova, Lucia Gharwalova, Alena Cejkova, Tomas Rezanka, Irena Kolouchova
