Article
Chemistry, Multidisciplinary
D. Kortus, V. Eigner, P. Lhotak
Summary: The oxidation of 2,14-dithiacalix[4]arene led to the selective formation of S-spiro derivatives, indicating that the thiacalixarene fragment is more prone to spirocyclization than the calixarene one. Acid-induced rearrangement of the S-spiro compound resulted in a novel phenoxathiin-based calixarene macrocycle. The conformational preferences of these new inherently chiral macrocycles were studied using NMR spectroscopy, single-crystal X-ray analysis, and DFT calculations.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Biotechnology & Applied Microbiology
Yaoyao Zhou, Feifei Ke, Luyi Chen, Yuele Lu, Linjiang Zhu, Xiaolong Chen
Summary: Sucrose phosphorylase (SPase) was engineered to enhance its regioselectivity and substrate specificity using a loop engineering strategy. The mutant obtained exhibited near-perfect control over the synthesis of a specific product. This work demonstrates the successful modulation of regioselectivity and specificity of SPase through loop engineering.
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
(2022)
Review
Chemistry, Applied
Supriya Rej, Amrita Das, Tarun K. Panda
Summary: The hydroboration of alkynes is a significant method for synthesizing important vinylborane compounds, with implications for regioselectivity and stereoselectivity. Extensive studies have been conducted on catalytic conditions and mechanistic studies to selectively obtain a single isomer, aiming to provide readers with accurate knowledge of available catalytic systems for this reaction. Researchers are encouraged to explore new catalytic systems to achieve the remarkable process of hydroboration of alkynes.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Tai-Ping Zhou, Fangrui Zhong, Yuzhou Wu, Rong-Zhen Liao
Summary: In this study, the reaction mechanism, regioselectivity, and stereoselectivity of the photochemical intramolecular [2 + 2] cycloaddition reaction catalyzed by a chiral thioxanthone molecule were investigated using quantum chemical calculations. The first C-C bond formation was identified as the rate-limiting and selectivity-controlling step, with the stereoselectivity being interaction-controlled. Moreover, the effects of catalyst substituents on the stereoselectivity of the photocycloadditions were explored, providing valuable mechanistic information for related photoinduced reactions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Physical
Chun-Chi Chen, Meng Dai, Lilan Zhang, Jing Zhao, Wei Zeng, Min Shi, Jian-Wen Huang, Weidong Liu, Rey-Ting Guo, Aitao Li
Summary: We investigated the mechanism of the P450tol enzyme from Rhodococcus coprophilus TC-2, which can hydroxylate toluene at the benzylic site. We solved the crystal structures of P450tol and its complex with the substrate, revealing how P450tol restricts the binding position of toluene and enables precise hydroxylation at the benzylic site. Additionally, we found that P450tol can also hydroxylate larger substrates and synthesized a self-sufficient chimeric enzyme with improved activity and stability. These findings highlight the potential of P450tol in biotechnological and pharmaceutical applications.
Review
Chemistry, Physical
Sahil Verma, Rahul Narayanlal Choudhary, Akash Prakash Kanadje, Uttam Chand Banerjee
Summary: Hydrolases, particularly lipases, play a significant role in the pharmaceutical industry by catalyzing the hydrolysis of ester bonds with high specificity and robustness, making them suitable for various organic synthesis procedures. Genetic engineering has further enhanced the catalytic capabilities of lipases, allowing for the development of customized enzymes for greener biocatalytic drug synthesis. Lipases may also play a key role in developing cascade reactions in organic synthesis, making them a promising candidate for future biocatalytic research in the pharmaceutical industry.
Article
Plant Sciences
Avesh Chadee, Masoom Mohammad, Greg C. Vanlerberghe
Summary: In this study, the expression of AOX1a gene in Nicotiana tabacum leaf was found to be influenced by leaf carbohydrate amounts and the relationship between source and sink activity. The expression of AOX1a gene increased when leaves were supplied with exogenous carbohydrates, grown at elevated CO2 concentrations, or subjected to various treatments. These findings offer important insights into the regulation of source-sink balance, photosynthesis, and phloem loading capacity in plants.
JOURNAL OF PLANT PHYSIOLOGY
(2022)
Article
Plant Sciences
Muhammad Asim, Mei Guo, Rayyan Khan, Yanguo Sun, Shasha Du, Wenting Liu, Yang Li, Xiaolin Wang, Mengyun Wang, Yi Shi, Yan Zhang
Summary: This study illustrates how sugar stimulates the onset of leaf senescence and controls sugar homeostasis through the T6P-SnRK and HXK signaling pathways.
PLANT PHYSIOLOGY AND BIOCHEMISTRY
(2022)
Article
Chemistry, Physical
Yeonjoo Lee, Hwiwoong Lee, Yurim Lee, Soohong Cho, Juhyung Lee, Joongoo Kang, Byunghyuck Jung, Yunmi Lee
Summary: Here, we report the Cu-catalyzed synthesis of α-borylmethyl-(E)-allylborons and the regioselective formation of doubleallylating diborons with diverse substituents. This method was applied to asymmetric and (Z)-selective allylation reactions, as well as asymmetric diastereo- and (E)-selective allyl transfer reactions. The key intermediate in the construction of the C7-C12 fragment of (-)-discodermolide was successfully synthesized.
Article
Chemistry, Multidisciplinary
Kazuki Inaba, Yuna Naito, Mina Tachibana, Kazunobu Toshima, Daisuke Takahashi
Summary: A regioselective and beta-stereospecific d-/l-arabinofuranosylation method has been developed for efficient synthesis of biologically active natural glycosides. The method showed high regioselectivity and yield with complete beta-stereoselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Yeonjoo Lee, Hwiwoong Lee, Yurim Lee, Soohong Cho, Juhyung Lee, Joongoo Kang, Byunghyuck Jung, Yunmi Lee
Summary: Copper-catalyzed synthesis of alpha-borylmethyl-(E)-allylborons was developed from readily available 1-substituted allenols and bis(pinacolato)diboron. This method enables the efficient and selective formation of doubleallylating diborons with diverse substituents, even at gram scale. The synthetic application of alpha-borylmethyl-(E)-allylborons was demonstrated by enantio- and (Z)selective allylation of aldehydes via Brunsted acid catalysis. Furthermore, Lewis acid catalyzed diastereo- and (E)-selective allyl transfer of (E)-allyldiborons to aldehydes generated (E)-allyl and (E)-homoallyl diols with excellent diastereoselectivity. The key intermediate for the construction of the C7-C12 fragment of (-)-discodermolide was also synthesized.
Review
Chemistry, Multidisciplinary
Yang Ke, Wei Li, Wenfeng Liu, Wangqing Kong
Summary: Scaffold diversity is crucial for the success of compound libraries in biological screening. This review focuses on recent efforts in Ni-catalyzed divergent and selective synthesis, which generate structurally diverse molecular scaffolds using the same substrate and varying the ligand backbone under almost identical reaction conditions. The progress achieved encourages the design and development of new selective catalytic systems and reveals new modes of catalytic transformation for broader synthetic applications.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Xiaoying He, Yan Li, Yehui Tao, Xuelian Qi, Ruiqi Ma, Honghua Jia, Ming Yan, Kequan Chen, Ning Hao
Summary: Sucrose phosphorylase (SPase, EC2.4.1.7) is an important enzyme for producing glycosylated compounds. In this study, an attempt was made to extracellularly express a recombinant SPase from Thermobacillus sp. in E. coli, but the enzyme was unexpectedly produced outside the cells. Truncation experiments showed that both termini of the enzyme are crucial for protein folding and enzymatic activity.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2021)
Article
Chemistry, Organic
Xinghua Zhang, Danna Lu, Zhenwei Wang
Summary: An efficient and green electrochemical method was described for alkyne difunctionalization without the use of oxidants. By using commercially available iodide radical and arylsulfonyl radical sources in an undivided electrochemical cell, a variety of (E)-beta-iodovinyl sulfones were obtained in one-pot with excellent regio- and stereoselectivity under mild and ecofriendly conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biotechnology & Applied Microbiology
Patrick J. Mason, Nam V. Hoang, Frederik C. Botha, Agnelo Furtado, Annelie Marquardt, Robert J. Henry
Summary: This study investigated the expression of gene families associated with UDP-G metabolism in sugarcane and found that UDP-G metabolism is closely related to carbon partitioning in sugarcane. The expression of sucrose synthetic genes was low in leaves but high in invertase genes. The expression of genes associated with sucrose, cellulose, and hemicellulose synthesis was low in source and storage sink organs, while genes related to UDP-G utilization and carbon flow were highly expressed in roots and immature internodes.
Article
Plant Sciences
Maurice G. L. Henquet, Neli Prota, Justin J. J. van der Hooft, Marina Varbanova-Herde, Raymond J. M. Hulzink, Martin de Vos, Marcel Prins, Michiel T. J. de Both, Maurice C. R. Franssen, Harro Bouwmeester, Maarten Jongsma
Article
Chemistry, Analytical
Fred A. M. G. van Geenen, Maurice C. R. Franssen, Han Zuilhof, Michel W. F. Nielen
ANALYTICAL CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Sjoerd Slagman, Wendy A. Jonkers, Han Zuilhof, Maurice C. R. Franssen
Article
Biochemical Research Methods
Fred A. M. G. van Geenen, Maurice C. R. Franssen, Ville Miikkulainen, Mikko Ritala, Han Zuilhof, Risto Kostiainen, Michel W. F. Nielen
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY
(2019)
Article
Chemistry, Multidisciplinary
Sjoerd Slagman, Sidharam P. Pujari, Maurice C. R. Franssen, Han Zuilhof
Article
Multidisciplinary Sciences
Qing Liu, Arman Beyraghdar Kashkooli, David Manzano, Irini Pateraki, Lea Richard, Pim Kolkman, Maria Fatima Lucas, Victor Guallar, Ric C. H. de Vos, Maurice C. R. Franssen, Alexander van der Krol, Harro Bouwmeester
NATURE COMMUNICATIONS
(2018)
Article
Chemistry, Physical
Alice Guarneri, Adrie H. Westphal, Jos Leertouwer, Joy Lunsonga, Maurice C. R. Franssen, Diederik J. Opperman, Frank Hollmann, Willem J. H. van Berkel, Caroline E. Paul
Article
Biochemical Research Methods
Fred A. M. G. van Geenen, Frank W. Claassen, Maurice C. R. Franssen, Han Zuilhof, Michel W. F. Nielen
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY
(2020)
Article
Plant Sciences
Annemiek van Zadelhoff, Wouter J. C. de Bruijn, Zhongxiang Fang, Emmanuel Gaquerel, Atsushi Ishihara, Daniele Werck-Reichhart, Pangzhen Zhang, Guangxiong Zhou, Maurice C. R. Franssen, Jean-Paul Vincken
Summary: Phenylalkenoic acid amides, also known as phenol amides or hydroxycinnamic acid amides, are bioactive phytochemicals that can have enhanced bioactivity through dimerization or oligomerization. By undergoing oxidative coupling, they can form (neo)lignanamides. The naming of these compounds lacks a systematic approach, prompting the proposal of a new systematic nomenclature.
JOURNAL OF NATURAL PRODUCTS
(2021)
Article
Agricultural Engineering
Goverdina C. H. Derksen, Frederique L. van Holthoon, Hendra M. Willemen, Cyrille A. M. Krul, Maurice C. R. Franssen, Teris A. van Beek
Summary: By adjusting extraction and fractionation parameters, the concentration of mutagenic compounds in madder can be minimized. The roots are stirred in water to reduce the concentration of specific mutagenic compounds to zero by endogenous enzymes, and further mutagenicity is reduced through heat treatment and chromatography.
INDUSTRIAL CROPS AND PRODUCTS
(2021)
Article
Food Science & Technology
Jeroen Peters, Edward Ash, Arjen Gerssen, Ruud Van Dam, Maurice C. R. Franssen, Michel W. F. Nielen
Summary: This study demonstrates the controlled biotransformation of ZEN glycosides by Cunninghamella strains, showing significant differences in the production of ZEN glycosides between different strains.
Article
Chemistry, Physical
Lia Martinez-Montero, Dirk Tischler, Philipp Suess, Anett Schallmey, Maurice C. R. Franssen, Frank Hollmann, Caroline E. Paul
Summary: A biocatalytic cascade was developed for the synthesis of enantioenriched azido alcohols, introducing chiral substituents through enzymatic epoxidation and regioselective cleavage reactions, leading to highly enantioenriched aromatic azido alcohols. This approach demonstrates the potential for practical production of these chiral compounds using two-component flavoprotein monooxygenases.
CATALYSIS SCIENCE & TECHNOLOGY
(2021)
Article
Microbiology
Constantinos Patinios, Lucrezia Lanza, Inge Corino, Maurice C. R. Franssen, John van der Oost, Ruud A. Weusthuis, Serve W. M. Kengen
FRONTIERS IN MICROBIOLOGY
(2020)
Article
Chemistry, Analytical
Fred A. M. G. van Geenen, Maurice C. R. Franssen, Anton H. M. Schotman, Han Zuilhof, Michel W. F. Nielen
ANALYTICAL CHEMISTRY
(2017)
Review
Biochemistry & Molecular Biology
Sjoerd Slagman, Han Zuilhof, Maurice C. R. Franssen