Article
Chemistry, Multidisciplinary
Andrew Whyte, Jonathan Bajohr, Ramon Arora, Alexa Torelli, Mark Lautens
Summary: An enantioselective consecutive cyclization/coupling process catalyzed by palladium was reported in this study. The stereoinduction was achieved through an enantioselective carbopalladation, leading to the generation of an intermediate that promotes a nucleopalladation step. This dual cyclization sequence was compatible with various nucleophiles and aryl iodides, producing numerous bisheterocycles in good yields and high regio- and enantioselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Jihoon Moon, Takusho Kin, Karin Mizuno, Shuji Akai, Kyohei Kanomata
Summary: This study presents a chemoenzymatic dynamic kinetic resolution (DKR) of racemic sec-alcohols using immobilized lipase and aqueous sulfuric acid as catalysts for kinetic resolution and racemization, respectively. The use of nanoparticle-stabilized phase separation in a Pickering emulsion allowed the use of these incompatible catalysts in a single vessel. The racemization reaction in the aqueous sulfuric acid solution effectively suppressed side reactions, resulting in high yields and optical purities.
Review
Chemistry, Organic
Tianyu Peng, Shixin Li, Dongxu Yang, Linqing Wang
Summary: Kinetic resolution is a practical method that selectively recovers enantiomerically pure starting materials and products from racemic mixtures. In this review, the less explored intramolecular kinetic resolution is discussed, highlighting its importance and elegance in generating chiral scaffolds. Different reaction types, including cyclization, elimination, isomerization, rearrangement, and miscellaneous reactions, are systematically presented and analyzed.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Veronique Michelet
Summary: The field of gold catalysis has been expanding continuously over the past 20 years, with the discovery of several new rearrangements. Key contributions in this area include the pi-activation of unsaturated substrates and the application of aryl, alkyne, alkene, or keto derivatives.
Article
Chemistry, Multidisciplinary
Benjamin Poelloth, Mukund P. Sibi, Hendrik Zipse
Summary: The factors responsible for the kinetic resolution of alcohols by chiral pyridine derivatives have been elucidated through accurate competitive linear regression analysis. Increasing the size of the aromatic side chain accelerates the reaction rate of the major enantiomer, leading to the design of a new catalyst with increased steric bulk for higher enantioselectivity values. Experimental and theoretical results suggest that the enhancement of enantioselectivity is achieved by accelerating the transformation of the major enantiomer through attractive non-covalent interactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Yu-Liang Pan, Ying-Bo Shao, Jie Wang, Zhen Liu, Li Chen, Xin Li
Summary: The method utilizes Bi(OAc)(3)/chiral phosphoric acid catalysis to achieve kinetic resolution of azirines efficiently, with good tolerance towards different substrates and reagents, demonstrating strong synthetic utility. Computational studies indicate the importance of weak interactions for enantioselectivity, and the impact of different metal acetates and counteranions on the reaction outcome.
Article
Chemistry, Multidisciplinary
Di Zhang, Youyuan Xiong, Yingjie Guo, Lei Zhang, Zheng Wang, Kuiling Ding
Summary: In this study, a Pd-catalyzed enantioselective domino Heck carbonylation reaction was developed using o-iodoacrylanilides, terminal alkynes, and water as nucleophiles. The reaction afforded a diverse range of beta-carbonylated 2-oxindole derivatives with a 3,3-disubstituted all-carbon quaternary stereocenter in high yields and good to excellent enantioselectivities. The synthetic utility of the methodology was demonstrated through gram-scale synthesis of various compounds, showcasing its potential for efficient chiral 2-oxindole synthesis.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Shaomin Chen, Rongxian Bai, Minghao Li, Ping Liu, Yanlong Gu
Summary: Adding an additive-like component to induce acid-acid-catalyzed tandem reactions can enrich method diversity, simplify operation, and enhance synthetic efficiency.
Article
Chemistry, Multidisciplinary
Jose A. Carmona, Patricia Rodriguez-Salamanca, Rosario Fernandez, Jose M. Lassaletta, Valentin Hornillos
Summary: An atroposelective Ir-catalyzed dynamic kinetic resolution (DKR) of 2-(quinolin-8-yl)benzaldehydes/1-naphthaldehydes is achieved by transfer hydrogenative coupling of allyl acetate. The reaction leads to the installation of central and axial chirality, with high diastereoselectivities and excellent enantioselectivities when ortho-cyclometalated iridium-DM-BINAP is used as the catalyst. The racemization of the substrates is facilitated through a designed transient Lewis acid-base interaction between the quinoline nitrogen atom and the aldehyde carbonyl group.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Organic
Gangavara L. Thejashree, Eric Doris, Edmond Gravel, Irishi N. N. Namboothiri
Summary: Kinetic resolution and dynamic kinetic resolution are common methods to access enantiomerically enriched compounds, with the latter achieving complete transformation through the process of racemization and further resolution. This review summarizes the dual catalytic strategies applied in kinetic resolution and dynamic kinetic resolution, focusing on the role of the two catalysts, compatibility between them, and practical benefits.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Biochemistry & Molecular Biology
Leonid A. Shaposhnikov, Svyatoslav S. Savin, Vladimir I. Tishkov, Anastasia A. Pometun
Summary: This review compares the structure, kinetic parameters, physiological role, and potential applications of different types of ribonucleoside hydrolases discovered and isolated from different organisms.
Article
Chemistry, Multidisciplinary
Cristian Andrei Gal, Laura Edit Barabas, Judith-Hajnal Bartha Vari, Madalina Elena Moisa, Diana Balogh-Weiser, Laszlo Csaba Bencze, Laszlo Poppe, Csaba Paizs, Monica Ioana Tosa
Summary: An efficient nanobioconjugate of lipase B was prepared and tested for the enzymatic kinetic resolution of racemic secondary 1-arylethan-1-ols. Various process parameters were investigated to determine the conditions for highest productivity, enabling hundred gram scale resolution with minimal biocatalyst usage. The long-term activity and selectivity of the biocatalyst were preserved throughout the study.
REACTION CHEMISTRY & ENGINEERING
(2021)
Review
Chemistry, Organic
Helene Pellissier
Summary: Organocatalytic dynamic kinetic resolution (DKR) has emerged as a promising field in the past two decades, allowing efficient separation of chiral compounds. This review aims to provide an update on organocatalytic DKRs since 2016.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Organic
Austin Pounder, Eric Neufeld, Peter Myler, William Tam
Summary: This review provides a comprehensive overview of transition-metal-catalyzed domino reactions of strained bicyclic alkenes, including both homo- and heterobicyclic alkenes. These compounds serve as important building blocks in organic synthesis, enabling the construction of biologically/medicinally relevant compounds with multiple stereocenters. The review is categorized based on the metal used in the reaction, and discusses the substrate scope, reaction conditions, and potential applications in organic synthesis. It also presents a comprehensive outlook on the reactivity paradigms of homo- and heterobicyclic alkenes, offering insights into future directions for further advancement in this field.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Ken Okuno, Yasuaki Furuya, Seiji Shirakawa
Summary: The kinetic resolution of racemic compounds is a reliable method to prepare chiral molecules in highly optically enriched forms. However, the kinetic resolution of racemic carboxylic acids has not been well developed. Esterification and lactonization promoted by chiral organocatalysts have been found to be effective methods for the kinetic resolution of chiral carboxylic acids.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Nanoscience & Nanotechnology
Shuhao Zhang, Julia Bramski, Murat Tutus, Joerg Pietruszka, Alexander Boeker, Stefan Reinicke
ACS APPLIED MATERIALS & INTERFACES
(2019)
Article
Chemistry, Organic
Patrick Ullrich, Julie Schmauck, Marcus Brauns, Marvin Mantel, Martin Breugst, Jorg Pietruszka
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Biochemistry & Molecular Biology
Marius Hoffmann, Marc R. Hayes, Joerg Pietruszka, Lothar Elling
GLYCOCONJUGATE JOURNAL
(2020)
Article
Chemistry, Multidisciplinary
Anja Weber, Martin Breugst, Joerg Pietruszka
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Alexander V. Fejzagic, Sebastian Myllek, Fabian Hogenkamp, Julian Greb, Joerg Pietruszka, Thomas Classen
Article
Biochemistry & Molecular Biology
Lena Berning, David Schluetermann, Annabelle Friedrich, Niklas Berleth, Yadong Sun, Wenxian Wu, Maria Jose Mendiburo, Jana Deitersen, Hannah U. C. Brass, Margaretha A. Skowron, Michele J. Hoffmann, Gunter Niegisch, Joerg Pietruszka, Bjorn Stork
Summary: Prodigiosin has been shown to block autophagy and sensitize cisplatin-resistant cells to apoptotic cell death in urothelial carcinoma cells. It exhibits potent anticancer activity with nanomolar IC50 values and synergistic effects when combined with cisplatin. The effects of prodigiosin are partially mediated by altering lysosomal function, making it a promising candidate for therapy of cisplatin-resistant urothelial carcinomas.
Article
Chemistry, Multidisciplinary
Marvin Mantel, Markus Giesler, Marian Guder, Elisabeth Ruethlein, Laura Hartmann, Joerg Pietruszka
Summary: Efficient synthesis of enantiopure key building blocks for natural product syntheses can be achieved by utilizing multiple catalytic steps within the same reaction vessel using two catalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Lea Winand, Pascal Schneider, Sebastian Kruth, Nico-Joel Greven, Wolf Hiller, Marcel Kaiser, Joerg Pietruszka, Markus Nett
Summary: By combining chemical synthesis with pathway refactoring, a series of physostigmine analogues with altered specificity and toxicity profiles were produced in the heterologous host. Among the compounds generated, the promising drug candidate phenserine was included, which was previously only accessible through total synthesis. This study provides a new approach for the development of novel therapeutics.
Article
Biochemistry & Molecular Biology
Fabian Hogenkamp, Fabienne Hilgers, Nora Lisa Bitzenhofer, Vera Ophoven, Mona Haase, Claus Bier, Dennis Binder, Karl-Erich Jaeger, Thomas Drepper, Jorg Pietruszka
Summary: Research on the use of photocaged compounds for controlling gene expression in bacteria synthesized six photocaged carbohydrates, successfully applied in E. coli. The study found that carbonate and carbamate bonds were convenient for linkage, and also discussed challenges and potential solutions during both photocaged inducer synthesis and application.
Article
Chemistry, Organic
Patrick Ullrich, Max A. Schlamkow, Ching-Yi Choi, Hannah Kerkenpass, Birgit Henssen, Jorg Pietruszka
Summary: In this study, tetraol-protected alpha-chiral allylboronates were used for the diastereo- and enantioselective transformations of cyclic imines, showing high efficiency and stability. The consecutive one-pot sequence for in situ formed N-unsubstituted imines provided selective access to all four stereoisomers of homoallylamine in minutes, demonstrating the utility and tunability of tetraol-based allylboronates.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Martin Waescher, Thomas Classen, Joerg Pietruszka
Summary: Enzyme immobilization is a technology that allows (bio-)catalysts to be used in continuous-flow systems. Different methods of immobilization have individual advantages and disadvantages. This study evaluated the performance of various simple and readily available immobilization methods on the enzyme 2-deoxy-D-ribose-5-phosphate aldolase (DERA) under continuous-flow conditions. The results showed that the metal-ion affinity-based approach performed better than other methods in terms of activity and stability.
Article
Biochemistry & Molecular Biology
Saskia Spitzer, Jasmin Wloka, Joerg Pietruszka, Oliver Kayser
Summary: This study utilized the highly promiscuous enzyme NphB to synthesize a library of synthetic cannabinoids by converting novel olivetolic acid derivatives. The substrates were characterized using in silico experiments and were further synthesized and analyzed in vitro. The resulting products were identified as CBGA derivatives, demonstrating the potential of these substrates in cannabinoid biosynthesis.
Article
Chemistry, Physical
Tim Moritz Weber, Alexandra Leyens, Lena Berning, Bjoern Stork, Joerg Pietruszka
Summary: This study investigated the synthesis and biological activities of Prodiginin and its derivatives. Different MBC derivatives were synthesized and tested with ligating enzymes, revealing that certain A-ring substituted prodiginines showed superior toxicity against cisplatin-resistant cancer cells. These findings contribute to the development of compounds with stronger anticancer activity against cisplatin-resistant cells.
CATALYSIS SCIENCE & TECHNOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Stefanie Brands, Hannah U. C. Brass, Andreas S. Klein, Joerg Pietruszka, Anna Joelle Ruff, Ulrich Schwaneberg
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Stefan Reinicke, Thilo Fischer, Julia Bramski, Joerg Pietruszka, Alexander Boeker
