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)
Review
Engineering, Environmental
Adeyemi S. Adeleye, Jie Xue, Yixin Zhao, Alicia A. Taylor, Jenny E. Zenobio, Yian Sun, Ziwei Han, Omobayo A. Salawu, Yurong Zhu
Summary: Pharmaceuticals and personal care products (PPCPs) are commonly found in wastewater and the environment, primarily entering municipal wastewater systems through human excretion and also from hospitals, PPCPs manufacturers, and agriculture. The most abundant PPCPs in raw wastewater include analgesics, antibiotics, and stimulants. In conventional wastewater treatment plants, most removal of PPCPs occurs during secondary treatment, with an overall removal rate exceeding 90%.
JOURNAL OF HAZARDOUS MATERIALS
(2022)
Article
Chemistry, Organic
Graham A. Hudson, Annie R. Hooper, Adam J. DiCaprio, David Sarlah, Douglas A. Mitchell
Summary: The study successfully identified and synthesized a new class of natural products, named pyritides, using a combination of bioinformatics, enzymology, and synthetic methods. These pyritides have a unique structure distinct from thiopeptides, with predicted enzymatic reactions leading to the formation of a trisubstituted pyridine-based macrocycle. The research demonstrates the potential of integrating bioinformatics, enzymology, and synthesis to characterize novel natural product scaffolds with interesting structural features and biological activities.
Article
Chemistry, Multidisciplinary
Cedric Couturier, Sebastian Gross, Alexander von Tesmar, Judith Hoffmann, Selina Deckarm, Anouchka Fievet, Nelly Dubarry, Thomas Taillier, Christoph Poeverlein, Heike Stump, Michael Kurz, Luigi Toti, Sabine Haag Richter, Dietmar Schummer, Philippe Sizun, Michael Hoffmann, Ram Prasad Awal, Nestor Zaburannyi, Kirsten Harmrolfs, Joachim Wink, Emilie Lessoud, Thierry Vermat, Veronique Cazals, Sandra Silve, Armin Bauer, Michael Mourez, Laurent Fraisse, Corinne Leroi-Geissler, Astrid Rey, Stephanie Versluys, Eric Bacque, Rolf Mueller, Stephane Renard
Summary: This article describes the myxobacterial natural product Corramycin isolated from Corallococcus coralloides. Corramycin exhibits anti-Gram-negative activity against Escherichia coli and is taken up via two transporter systems. The biosynthetic gene cluster (BGC) of Corramycin was identified and a biosynthesis model was proposed. The absolute configuration of the molecule was elucidated through bioinformatic analysis and total synthesis. Animal experiments confirmed the antibacterial effect of Corramycin.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Yusuke Imamura, Kyohei Takaoka, Yuma Komori, Masanori Nagatomo, Masayuki Inoue
Summary: This study presents a 34-step synthesis of Taxol, involving inter- and intramolecular radical reactions to connect the A- and C-ring fragments and cyclize the B-ring. The A- and C-ring functional groups were then efficiently modified using newly developed selective reactions. The construction of the D-ring and its conjugation with the beta-amino acid led to the successful synthesis of Taxol. This synthesis provides useful insights for the design of multistep syntheses of diverse bioactive natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Prabhakara R. Tharra, Andrey A. Mikhaylov, Jiri Svejkar, Marina Gysin, Sven N. Hobbie, Jakub Svenda
Summary: We report a concise synthesis method for the naturally occurring protein synthesis inhibitor (+)-actinobolin. The complex molecular structure of 1 was assembled using (-)-quinic acid, L-threonine, and L-alanine. Our simplified synthesis route, consisting of 9 steps with 18% overall yield, has practical applications for analog preparation, as shown in this study.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Lisa-Catherine Rosenbaum, Maximilian Haefner, Tanja Gaich
Summary: A racemic and scalable enantioselective total synthesis of (+)-waihoensene was achieved, featuring an angular triquinane substructure with an all-cis-fused tetracyclic backbone and six contiguous stereocenters, four of which are quaternary. Enantioselectivity was introduced at an early stage, and key structural features were efficiently installed through several diastereoselective reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Medicinal
Yueting Deng, Yang Liu, Juan Li, Xiao Wang, Shan He, Xiaojun Yan, Yutong Shi, Weiyan Zhang, Lijian Ding
Summary: Biofilm is a complex microbial consortium with resistance mechanisms to known antibiotics, posing a threat to human health. Marine organisms provide abundant resources for the development of anti-biofilm agents.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Georg Niggemeyer, Anastasia Knyazeva, Raphael Gasper, Dale Corkery, Pia Bodenbinder, Julian J. Holstein, Sonja Sievers, Yao-Wen Wu, Herbert Waldmann
Summary: Design and synthesis of pseudo-natural products through recombination of natural product fragments enables the discovery of novel biologically relevant chemical matter. In this study, the combination of this principle with macrocycle formation was described, leading to the efficient synthesis of 163 macrocyclic pseudo-natural products. Biological investigation revealed their potent inducers of autophagy-related processes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Microbiology
Polpass Arul Jose, Anjisha Maharshi, Bhavanath Jha
Summary: Actinobacteria are recognized as important biosynthetic factories that produce a wide range of secondary metabolites. Recent genomic insights have impacted the exploitation and discovery of new compounds from these metabolically active bacteria, leading to significant progress in the field of drug discovery.
MICROBIOLOGICAL RESEARCH
(2021)
Review
Chemistry, Multidisciplinary
Lauren G. O'Neil, John F. Bower
Summary: Classical amination methods involve the reaction of a nitrogen nucleophile with an electrophilic carbon center; however, in recent years, umpoled strategies have gained traction where the nitrogen source acts as an electrophile. A wide range of electrophilic aminating agents are now available, and these underpin a range of powerful C-N bond-forming processes. In this Review, we highlight the strategic use of electrophilic aminating agents in total synthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
David L. Kukla, Juan Canchola, Joseph D. Rosenthal, Jonathan J. Mills
Summary: In this study, researchers synthesized a library of analogues to explore the structure-activity relationships of the natural products. They found compound 7 to be 4-fold more potent against MRSA than the natural product, and identified a 2-hydroxypyridine analogue with equal potency but significantly reduced hemolytic activity.
CHEMICAL BIOLOGY & DRUG DESIGN
(2021)
Article
Chemistry, Organic
Tsuyoshi Murata, Kenta Yoshida, Shuichi Suzuki, Akira Ueda, Shinsuke Nishida, Junya Kawai, Kozo Fukui, Kazuhiro Nakasuji, Yasushi Morita
Summary: Tri-tert-butylated 4,7-dihydroxyphenalenone derivative was synthesized from a corresponding 4,9-dimethoxyphenalenone derivative through regioselective deoxygenation/oxygenation. The derivative exhibited chromic behavior accompanied by protonation and deprotonation, resulting in monocation and dianion species, respectively. The C-3 symmetric electronic structures of these species were elucidated using experimental and theoretical methods.
Review
Chemistry, Multidisciplinary
Debobrata Paul, Ashis Kundu, Sanu Saha, Rajib Kumar Goswami
Summary: This feature article highlights total synthesis as a reliable tool for confirming the structure of natural products. Despite advances in spectroscopic techniques, structural misassignments of natural products remain common. Recent case studies have shown that chemical synthesis can be used to revise the structures of natural products.
CHEMICAL COMMUNICATIONS
(2021)
Article
Biochemistry & Molecular Biology
Yanan Du, Anyarat Thanapipatsiri, Kenichi Yokoyama
Summary: Nucleoside natural products have diverse biological activities and can be used for various applications, including medicine and agriculture. Previous studies have revealed the biosynthetic mechanisms of these nucleosides, involving early steps classified into two types and downstream tailoring enzymes for structural diversity. By investigating two enzymes representing these types of modifications, it is possible to discover putative nucleoside biosynthetic gene clusters and predict core nucleoside structures, suggesting the potential for future discovery of novel nucleoside natural products.
