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Keywords = tripotassium phosphate

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10 pages, 1316 KiB  
Communication
Palladium-Catalyzed α-Arylation of Esters: Synthesis of the Tetrahydroisoquinoline Ring
by Georgeta Serban and Faïza Diaba
Reactions 2025, 6(1), 17; https://doi.org/10.3390/reactions6010017 - 1 Mar 2025
Cited by 1 | Viewed by 1131
Abstract
The palladium-catalyzed cross-coupling reaction used for carbon–carbon bond formation is one of the most commonly applied reactions in modern organic synthesis. In this work, a concise strategy was developed for constructing the tetrahydroisoquinoline core, a key structural motif found in many biologically active [...] Read more.
The palladium-catalyzed cross-coupling reaction used for carbon–carbon bond formation is one of the most commonly applied reactions in modern organic synthesis. In this work, a concise strategy was developed for constructing the tetrahydroisoquinoline core, a key structural motif found in many biologically active compounds. This method involves the palladium-catalyzed intramolecular coupling of aryl iodides with ester enolates generated in the presence of K3PO4 as a base, resulting in the formation of the tetrahydroisoquinoline ring with an exceptionally high yield of 84%. Full article
(This article belongs to the Special Issue Feature Papers in Reactions in 2025)
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21 pages, 3972 KiB  
Article
Identification, Analysis and Gene Cloning of the SWEET Gene Family Provide Insights into Sugar Transport in Pomegranate (Punica granatum)
by Xinhui Zhang, Sha Wang, Yuan Ren, Chengyan Gan, Bianbian Li, Yaoyuwei Fan, Xueqing Zhao and Zhaohe Yuan
Int. J. Mol. Sci. 2022, 23(5), 2471; https://doi.org/10.3390/ijms23052471 - 23 Feb 2022
Cited by 24 | Viewed by 3673
Abstract
Members of the sugars will eventually be exported transporter (SWEET) family regulate the transport of different sugars through the cell membrane and control the distribution of sugars inside and outside the cell. The SWEET gene family also plays important roles in plant growth [...] Read more.
Members of the sugars will eventually be exported transporter (SWEET) family regulate the transport of different sugars through the cell membrane and control the distribution of sugars inside and outside the cell. The SWEET gene family also plays important roles in plant growth and development and physiological processes. So far, there are no reports on the SWEET family in pomegranate. Meanwhile, pomegranate is rich in sugar, and three published pomegranate genome sequences provide resources for the study of the SWEET gene family. 20 PgSWEETs from pomegranate and the known Arabidopsis and grape SWEETs were divided into four clades (Ⅰ, Ⅱ, Ⅲ and Ⅳ) according to the phylogenetic relationships. PgSWEETs of the same clade share similar gene structures, predicting their similar biological functions. RNA-Seq data suggested that PgSWEET genes have a tissue-specific expression pattern. Foliar application of tripotassium phosphate significantly increased the total soluble sugar content of pomegranate fruits and leaves and significantly affected the expression levels of PgSWEETs. The plant growth hormone regulator assay also significantly affected the PgSWEETs expression both in buds of bisexual and functional male flowers. Among them, we selected PgSWEET17a as a candidate gene that plays a role in fructose transport in leaves. The 798 bp CDS sequence of PgSWEET17a was cloned, which encodes 265 amino acids. The subcellular localization of PgSWEET17a showed that it was localized to the cell membrane, indicating its involvement in sugar transport. Transient expression results showed that tobacco fructose content was significantly increased with the up-regulation of PgSWEET17a, while both sucrose and glucose contents were significantly down-regulated. The integration of the PgSWEET phylogenetic tree, gene structure and RNA-Seq data provide a genome-wide trait and expression pattern. Our findings suggest that tripotassium phosphate and plant exogenous hormone treatments could alter PgSWEET expression patterns. These provide a reference for further functional verification and sugar metabolism pathway regulation of PgSWEETs. Full article
(This article belongs to the Section Molecular Plant Sciences)
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14 pages, 4619 KiB  
Article
Aqueous Biphasic Systems Comprising Natural Organic Acid-Derived Ionic Liquids
by Maria V. Quental, Matheus M. Pereira, Francisca A. e Silva, João A. P. Coutinho and Mara G. Freire
Separations 2022, 9(2), 46; https://doi.org/10.3390/separations9020046 - 7 Feb 2022
Cited by 5 | Viewed by 3802
Abstract
Despite the progress achieved by aqueous biphasic systems (ABSs) comprising ionic liquids (ILs) in extracting valuable proteins, the quest for bio-based and protein-friendly ILs continues. To address this need, this work uses natural organic acids as precursors in the synthesis of four ILs, [...] Read more.
Despite the progress achieved by aqueous biphasic systems (ABSs) comprising ionic liquids (ILs) in extracting valuable proteins, the quest for bio-based and protein-friendly ILs continues. To address this need, this work uses natural organic acids as precursors in the synthesis of four ILs, namely tetrabutylammonium formate ([N4444][HCOO]), tetrabutylammonium acetate ([N4444][CH3COO]), tetrabutylphosphonium formate ([P4444][HCOO]), and tetrabutylphosphonium acetate ([P4444][CH3COO]). It is shown that ABSs can be prepared using all four organic acid-derived ILs paired with the salts potassium phosphate dibasic (K2HPO4) and tripotassium citrate (C6H5K3O7). According to the ABSs phase diagrams, [P4444]-based ILs outperform their ammonium congeners in their ability to undergo liquid–liquid demixing in the presence of salts due to their lower hydrogen-bond acidity. However, deviations to the Hofmeister series were detected in the salts’ effect, which may be related to the high charge density of the studied IL anions. As a proof of concept for their extraction potential, these ABSs were evaluated in extracting human transferrin, allowing extraction efficiencies of 100% and recovery yields ranging between 86 and 100%. To further disclose the molecular-level mechanisms behind the extraction of human transferrin, molecular docking studies were performed. Overall, the salting-out exerted by the salt is the main mechanism responsible for the complete extraction of human transferrin toward the IL-rich phase, whereas the recovery yield and protein-friendly nature of these systems depend on specific “IL-transferrin” interactions. Full article
(This article belongs to the Special Issue Research on Sustainable Extraction and Purification of Compounds)
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19 pages, 29312 KiB  
Article
Synthesis of Functionalized Thiophene Based Pyrazole Amides via Various Catalytic Approaches: Structural Features through Computational Applications and Nonlinear Optical Properties
by Iram Kanwal, Nasir Rasool, Syeda Huda Mehdi Zaidi, Zainul Amiruddin Zakaria, Muhammad Bilal, Muhammad Ali Hashmi, Adeel Mubarik, Gulraiz Ahmad and Syed Adnan Ali Shah
Molecules 2022, 27(2), 360; https://doi.org/10.3390/molecules27020360 - 7 Jan 2022
Cited by 13 | Viewed by 4472
Abstract
In the present study, pyrazole-thiophene-based amide derivatives were synthesized by different methodologies. Here, 5-Bromothiophene carboxylic acid (2) was reacted with substituted, unsubstituted, and protected pyrazole to synthesize the amide. It was observed that unsubstituted amide (5-bromo-N-(5-methyl-1H-pyrazol-3-yl)thiophene-2-carboxamide ( [...] Read more.
In the present study, pyrazole-thiophene-based amide derivatives were synthesized by different methodologies. Here, 5-Bromothiophene carboxylic acid (2) was reacted with substituted, unsubstituted, and protected pyrazole to synthesize the amide. It was observed that unsubstituted amide (5-bromo-N-(5-methyl-1H-pyrazol-3-yl)thiophene-2-carboxamide (7) was obtained at a good yield of about 68 percent. The unsubstituted amide (7) was arylated through Pd (0)-catalyzed Suzuki–Miyaura cross-coupling, in the presence of tripotassium phosphate (K3PO4) as a base, and with 1,4-dioxane as a solvent. Moderate to good yields (66–81%) of newly synthesized derivatives were obtained. The geometry of the synthesized compounds (9a9h) and other physical properties, like non-linear optical (NLO) properties, nuclear magnetic resonance (NMR), and other chemical reactivity descriptors, including the chemical hardness, electronic chemical potential, ionization potential, electron affinity, and electrophilicity index have also been calculated for the synthesized compounds. In this study, DFT calculations have been used to investigate the electronic structure of the synthesized compounds and to compute their NMR data. It was also observed that the computed NMR data manifested significant agreement with the experimental NMR results. Furthermore, compound (9f) exhibits a better non-linear optical response compared to all other compounds in the series. Based on frontier molecular orbital (FMO) analysis and the reactivity descriptors, compounds (9c) and (9h) were predicted to be the most chemically reactive, while (9d) was estimated to be the most stable among the examined series of compounds. Full article
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