Article
Multidisciplinary Sciences
Fangyuan Wang, Zongpeng Zhang, Yu Chen, Virginie Ratovelomanana-Vidal, Peiyuan Yu, Gen-Qiang Chen, Xumu Zhang
Summary: In this study, a method for synthesizing 3,4-disubstituted succinimides is reported, and the origin of stereoselectivity is elucidated through experimental and theoretical investigations. The method exhibits high catalytic activity and stereoselectivity, and different configurations of products can be obtained by controlling reaction conditions. This study provides a straightforward and stereodivergent approach for synthesizing enantioenriched succinimides of significant enzymatic selectivity from inexpensive chemical feedstocks in a single reaction step.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Anna Morandini, Arianna Rossetti, Alessandro Sacchetti
Summary: This study presents a novel biocatalyzed pathway for the preparation of a chiral amine precursor through resolution study of a key alcohol intermediate.
Article
Chemistry, Multidisciplinary
Yue Wang, Er-Qing Li, Zheng Duan
Summary: The development of stereodivergent strategies in asymmetric synthesis is crucial for accessing the full range of stereoisomers in products with multiple stereocenters. In this study, a novel P-chirogenic ligand, YuePhos, was developed to achieve precise switching of product stereochemistry in a Pd-catalyzed asymmetric cycloaddition reaction. The method provides an efficient route for the synthesis of pyrrolidines with up to three adjacent stereocenters, with excellent enantiomeric excesses.
Article
Chemistry, Multidisciplinary
Byungjun Kim, Yuna Song, Sarah Yunmi Lee
Summary: In this study, a silver-catalyzed method was developed for the enantio- and diastereodivergent synthesis of chiral pyroglutamic acid esters with multiple stereocenters. By utilizing catalyst control and stereospecificity, all four product stereoisomers containing two adjacent stereocenters can be accessed with high stereoselectivity.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Chong Shen, Xiang Cheng, Liang Wei, Ruo-Qing Wang, Chun-Jiang Wang
Summary: The study reported a method for rapid construction of multiple C-C bonds using a single catalyst, successfully synthesizing various pseudo-C-2 symmetrical cyanoacetate derivatives and developing a more challenging sequential allylic alkylation method, which can produce products with three contiguous stereocenters.
Article
Chemistry, Medicinal
Kengo Kasama, Yuya Hinami, Karin Mizuno, Satoshi Horino, Tomoya Nishio, Chiharu Yuki, Kyohei Kanomata, Gamal A. I. Moustafa, Harald Groger, Shuji Akai
Summary: This study achieved the highly enantioselective lipase-catalyzed kinetic resolution for the synthesis of chiral C-1-symmetric biaryl compounds with heterocyclic moieties. The addition of disodium carbonate accelerated the enzymatic esterification without compromising its enantioselectivities. Furthermore, the combination of mesoporous silica-supported oxovanadium-catalyzed cross-dehydrogenative coupling and lipase-catalyzed kinetic resolution allowed the one-pot synthesis of optically active heterocyclic biaryl compounds with high optical purity.
CHEMICAL & PHARMACEUTICAL BULLETIN
(2022)
Article
Chemistry, Physical
Qin Xu, Kai-Shun Huang, Yuan-Fei Wang, Hui-Hui Wang, Bao-Dong Cui, Wen-Yong Han, Yong-Zheng Chen, Nan-Wei Wan
Summary: An efficient biocatalytic strategy for stereodivergent synthesis of chiral epoxides and oxazolidinones was developed by identifying and engineering halohydrin dehalogenases. This strategy achieved high yields and excellent enantioselectivity.
Review
Multidisciplinary Sciences
Raffaella Ferraccioli
Summary: Metal/lipase-combo catalyzed dynamic kinetic resolution (DKR) is a general and practical process to obtain enantiopure esters R with quantitative conversion. The use of various metal catalysts has expanded the substrate scope, including challenging compounds, and integration into cascade reactions can lead to linear/cyclic chiral molecules with high ee values.
Article
Chemistry, Multidisciplinary
Li Dai, Wen Liu, Yuqiao Zhou, Zi Zeng, Xinyue Hu, Weidi Cao, Xiaoming Feng
Summary: A highly enantioselective halogenation/semipinacol rearrangement has been developed using a chiral catalyst, leading to the synthesis of optically active compounds with a quaternary stereocenter under mild reaction conditions. The proposed catalytic cycle provides insight into the reaction process and enantiocontrol.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Muxing Zhou, Tatiana Gridneva, Zhenfeng Zhang, Ende He, Yangang Liu, Wanbin Zhang
Summary: This study presents an efficient route for the synthesis of chiral phthalidyl ester prodrugs using a chiral bicyclic imidazole organocatalyst and a continuous injection process. Computational studies suggest a general base catalytic mechanism different from the widely accepted nucleophilic catalytic mechanism. Analysis of key transition states reveals that CH-pi interactions, rather than previously considered cation/pi-pi interactions, play a dominant role in stereocontrol.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Yingtao Wu, Mingrui Li, Jiaqiong Sun, Guangfan Zheng, Qian Zhang
Summary: In this research, an NHC-catalyzed atroposelective esterification of biaryl dialdehydes is described as a general and practical strategy for the construction of axially chiral aldehydes. The method features excellent enantioselectivity, mild conditions, good functional-group tolerance, and applicability to late-stage functionalization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Biotechnology & Applied Microbiology
Chenming Huang, Junling Liu, Jiali Fang, Xian Jia, Zhendong Zheng, Song You, Bin Qin
Summary: This review discusses the advances in the research area of KRED-catalyzed asymmetric synthesis for biomanufacturing of chiral chemicals with at least two chiral centers through the kinetic resolution (KR) approach and the dynamic kinetic resolution (DKR) approach.
FRONTIERS IN BIOENGINEERING AND BIOTECHNOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Xu Shen, Congcong Huang, Xiang-Ai Yuan, Shouyun Yu
Summary: A photoredox-catalyzed iminoalkenylation of gamma-alkenyl O-acyl oximes has been developed, using readily available alkenylboronic acids as reagents to generate densely functionalized pyrrolines. Depending on the reaction solvent, either (E)- or (Z)-cinnamylpyrrolines can be obtained, with two stereocenters established with complete diastereoselectivity and only one diastereomer isolated through specific pathways.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Multidisciplinary Sciences
Chen Zhu, Huifeng Yue, Magnus Rueping
Summary: A new method is reported for the arylalkylation of alkynes, which combines electrochemistry and photocatalysis. This approach allows for the synthesis of a wide range of trisubstituted alkenes with high yields and excellent stereoselectivity.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Hu Huijuan, Yan Qiaoli, Lu Xiaogang, Yang Qifan, Pei Chengxin, Wang Hongmei, Gao Runli
Summary: This study presents a direct biocatalytic method for the synthesis of P-chiral phosphine derivatives. By using commercially available lipase from porcine pancreas (PPL), the reactions proceed efficiently under mild conditions, delivering high yields and enantioselectivity for a wide range of reaction partners.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Pawel Borowiecki, Mateusz Mlynek, Maciej Dranka
Summary: This study presents a concise chemoenzymatic route towards enantiomerically enriched active pharmaceutical ingredients, diprophylline and xanthinol nicotinate, using enantioselective lipase-mediated methanolysis. The method achieved high enantioselectivity and yield in producing key chlorohydrin intermediates, which were further converted into enantio-enriched active agents. Docking studies and X-ray diffraction analyses were also conducted to confirm the stereochemical outcomes and crystal structures of the synthesized APIs.
BIOORGANIC CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Anna Maria Dabrowska, Aleksander Hurko, Krzysztof Durka, Maciej Dranka, Pawel Horeglad
Summary: The manipulation of alkylgallium alkoxides structure with asymmetric N-heterocyclic carbenes (NHCs) can lead to on and off states of catalytic gallium centers in ring-opening polymerization, affecting activity and stereoselectivity. Different reactions with asymmetric NHCs resulted in formation of specific complexes, influencing the cavity required for interaction of lactide with gallium and alkoxide groups, and affecting the stereoselectivity of the reactions.
Article
Chemistry, Physical
Beata Zdun, Piotr Ciesla, Jan Kutner, Pawel Borowiecki
Summary: This study explores the enzymatic kinetic resolution (EKR) of 2-arylpropanoic acids and successfully obtains optically active products with moderate-to-good enantioselectivity through the optimization of reaction conditions.
Article
Biochemistry & Molecular Biology
Pawel Borowiecki, Aleksandra Rudzka, Tamara Reiter, Wolfgang Kroutil
Summary: This study reports a chemoenzymatic route towards xanthine-based enantiomerically pure active pharmaceutical ingredients using recombinant short-chain ADHs, achieving excellent enantiomeric excess and high yields for both (R)- and (S)-enantiomers. The biocatalytic method demonstrated in this work is straightforward and practical for the manufacturing of these pharmaceuticals.
BIOORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Pawel Borowiecki
Summary: In order to develop more effective and safer analgesics, a novel enantiomerically enriched ethereal analog of (R)-iso-moramide was designed and synthesized. This analog has improved affinity and selectivity towards opioid receptors and has the potential to be a powerful synthetic opiate. The synthesis involved several key steps and resulted in the desired product.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Inorganic & Nuclear
Urszula Maciolek, Ewaryst Mendyk, Daniel M. Kaminski, Maciej Dranka, Liliana Mazur, Anna Kuzniar, Jan Kalembkiewicz, Anna E. Koziol
Summary: New sodium complexes of quercetin-5'-sulfonic acid have been synthesized and their molecular and crystal structures have been determined by X-ray crystallography. The sodium cations form polymeric complexes by coordinating with oxygen atoms, and some solvent molecules also act as network bonding agents.
Article
Polymer Science
Maciej Debowski, Zbigniew Florjanczyk, Katarzyna Godlewska, Alicja Kaczmarczyk, Maciej Dranka, Andrzej Ostrowski
Summary: The synthesis, structure, and properties of coordination polymers composed of linear zinc bis(diorganophospate)s (ZnDOPs) were described. The morphology, thermal transformations, and solubility of ZnDOPs strongly depend on the type of organic substituent and the thermal history. ZnDOPs can undergo reversible dissociation in polar organic solvents, allowing for easy modification of their composition and properties via anion exchange.
Article
Chemistry, Physical
Beata Zdun, Izabela Kopinska, Maciej Dranka, Tamara Reiter, Wolfgang Kroutil, Pawel Borowiecki
Summary: The study successfully achieved the kinetic resolution of 1,2,3,4-tetrahydroquinoline-propan-2-ols, producing high optical purity (S)-alcohols and corresponding (R)-acetates, demonstrating spontaneous amplification of optical purity in one of the compounds.
Article
Chemistry, Organic
Beata Zdun, Tamara Reiter, Wolfgang Kroutil, Pawel Borowiecki
Summary: We developed chemoenzymatic routes using low-cost starting materials and enzyme preparations to synthesize tenofovir. The key step involved stereoselective reduction or kinetic resolution using alcohol dehydrogenase or lipase as biocatalysts. By employing immobilized lipase in a mixture of vinyl acetate and toluene, the desired (R)-ester was obtained with high yield and optical purity. Alternatively, reduction of a ketone using lyophilized E. coli cells containing recombinant alcohol dehydrogenase resulted in excellent conversion and yield of the corresponding (R)-alcohol. The enzymatic strategy could be applied in the synthesis of tenofovir prodrug derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Pharmacology & Pharmacy
Patrycja Winska, Monika Wielechowska, Miroslawa Koronkiewicz, Pawel Borowiecki
Summary: CK2 and PIM-1 are serine/threonine kinases involved in essential processes, and inhibiting their activity can reduce cancer cell viability. A series of novel inhibitors were designed and synthesized, and their effects on cancer cells were evaluated. The most active compound demonstrated high selectivity and proapoptotic properties, as well as induction of autophagy.
Article
Chemistry, Multidisciplinary
Aleksandra Rudzka, Beata Zdun, Natalia Antos, Lia Martinez Montero, Tamara Reiter, Wolfgang Kroutil, Pawel Borowiecki
Summary: There is a need for biocatalysts capable of transferring hydrogen to prepare optically pure alcohols, especially for sterically demanding ketones. This study describes the biocatalytic potential of an anti-Prelog (R)-specific variant of Lactobacillus kefir ADH as a whole-cell biocatalyst for the reduction of prochiral carbonyl substrates. The results show that the biocatalyst exhibits activity towards a variety of ketones, producing optically active alcohol products with high conversion and excellent stereoselectivity.
COMMUNICATIONS CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Joanna Bojarska, Martin Breza, Milan Remko, Pawel Borowiecki, Andrzej Fruzinski, Izabela D. Madura, Krzysztof Kaczmarek, Zbigniew Lesnikowski, Agata Kraj, Piotr Zielenkiewicz, Wojciech M. M. Wolf
Summary: In this study, a series of cyclopropyl-containing peptide-derived compounds were synthesized and their crystal structures were determined. The self-assembly mechanism and potential biological activity of these compounds were investigated. This research provides a basis and guidance for further applications of cyclopropyl-containing peptide-derived compounds.
Article
Chemistry, Multidisciplinary
Pawel Borowiecki, Beata Zdun, Natalia Popow, Magdalena Wiklinska, Tamara Reiter, Wolfgang Kroutil
Summary: Efficient chemoenzymatic routes were developed to synthesize both enantiomers of adrenergic beta-blockers using a central chiral building block and lipase-catalyzed kinetic resolution. The method allows for the synthesis of various enantiomerically enriched beta-blockers and offers potential industrial applications.
Article
Chemistry, Physical
Pawel Borowiecki, Aleksandra Rudzka, Tamara Reiter, Wolfgang Kroutil
Summary: In this study, a sequential chemoenzymatic one-pot two-step deracemization protocol was developed for synthesizing enantiomeric Lisofylline. The protocol involved a tandem bi-enzymatic oxidation-reduction reaction sequence, which catalyzed the oxidation of Lisofylline to pentoxifylline using laccase and a redox mediator, and the subsequent reduction of pentoxifylline to generate enantiomeric Lisofylline using alcohol dehydrogenases. The method showcased high conversion rates and synthesis efficiency, providing both antipodes of Lisofylline in good yields and high enantiomeric excess.
CATALYSIS SCIENCE & TECHNOLOGY
(2022)