ACS OmegaPub Date : 2024-11-01DOI: 10.1021/acsomega.4c0703010.1021/acsomega.4c07030
Letícia F. L. Machado, Luana S. Andrade, Dalmo Mandelli and Wagner A. Carvalho*,
{"title":"Iron-Modified Acid Carbons for the Conversion of Fructose to 5-Hydroxymethylfurfural under Microwave Heating","authors":"Letícia F. L. Machado, Luana S. Andrade, Dalmo Mandelli and Wagner A. Carvalho*, ","doi":"10.1021/acsomega.4c0703010.1021/acsomega.4c07030","DOIUrl":"https://doi.org/10.1021/acsomega.4c07030https://doi.org/10.1021/acsomega.4c07030","url":null,"abstract":"<p >Carbons with Brønsted acidic sites and iron oxide modifications were prepared through hydrothermal carbonization and glycerol pyrolysis in the presence of sulfuric acid, magnetite, and iron(III) nitrate. The solids were tested as catalysts in converting fructose to 5-hydroxymethylfurfural (5-HMF). Characterization techniques revealed a uniform presence of 4.89 mmol g<sup>–1</sup> total acidic groups, including up to 1.87 mmol g<sup>–1</sup> sulfonic and carboxylic groups. Combined with a reduced surface area, the Brønsted and Lewis acidity enabled the conversion of 94% of fructose with selectivity values as high as 95% for 5-HMF in just 10 min at 140 °C, using microwave heating and dimethyl sulfoxide (DMSO) as the solvent. This performance was attributed to the selective heating of the catalyst surface by the microwave absorption capacity of the acidic groups and iron oxide, leading to the formation of “hot spots.” The catalyst obtained by hydrothermal carbonization in the presence of Fe<sub>3</sub>O<sub>4</sub>, HCC-20% Fe<sub>3</sub>O<sub>4</sub>, demonstrated stability when reused for up to four consecutive cycles. A slight reduction in conversion and selectivity was observed after the first use, attributed to the presence of acid species not incorporated into the solid during the synthesis process.</p>","PeriodicalId":22,"journal":{"name":"ACS Omega","volume":null,"pages":null},"PeriodicalIF":3.7,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsomega.4c07030","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142608587","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ACS OmegaPub Date : 2024-11-01DOI: 10.1021/acsomega.4c0777610.1021/acsomega.4c07776
Kelsey M. Leong, Aileen Y. Sun, Mindy L. Quach, Carrie H. Lin, Cosette A. Craig, Felix Guo, Timothy R. Robinson, Megan M. Chang and Ayokunle O. Olanrewaju*,
{"title":"Democratizing Access to Microfluidics: Rapid Prototyping of Open Microchannels with Low-Cost LCD 3D Printers","authors":"Kelsey M. Leong, Aileen Y. Sun, Mindy L. Quach, Carrie H. Lin, Cosette A. Craig, Felix Guo, Timothy R. Robinson, Megan M. Chang and Ayokunle O. Olanrewaju*, ","doi":"10.1021/acsomega.4c0777610.1021/acsomega.4c07776","DOIUrl":"https://doi.org/10.1021/acsomega.4c07776https://doi.org/10.1021/acsomega.4c07776","url":null,"abstract":"<p >Microfluidics offer user-friendly liquid handling for a range of biochemical applications. 3D printing microfluidics is rapid and cost-effective compared to conventional cleanroom fabrication. Typically, microfluidics are 3D printed using digital light projection (DLP) stereolithography (SLA), but many models in use are expensive (≥$10,000 USD), limiting widespread use. Recent liquid crystal display (LCD) technology advancements have provided inexpensive (<$500 USD) SLA 3D printers with sufficient pixel resolution for microfluidic applications. However, there are only a few demonstrations of microfluidic fabrication, limited validation of print fidelity, and no direct comparisons between LCD and DLP printers. We compared a 40 μm pixel DLP printer (∼$18,000 USD) with a 34.4 μm pixel LCD printer (<$380 USD). Consistent with prior work, we observed linear trends between designed and measured channel widths ≥4 pixels on both printers, so we calculated accuracy above this size threshold. Using a standard IPA-wash resin and optimized parameters for each printer, the average error between designed and measured widths was 2.11 ± 1.26% with the DLP printer and 15.4 ± 2.57% with the 34.4 μm LCD printer. Printing with optimized conditions for a low-cost water-wash resin designed for LCD-SLA printers resulted in an average error of 2.53 ± 0.94% with the 34.4 μm LCD printer and 5.35 ± 4.49% with a 22 μm LCD printer. We characterized additional parameters including surface roughness, channel perpendicularity, and light intensity uniformity, and as an application of LCD-printed devices, we demonstrated consistent flow rates in capillaric circuits for self-regulated and self-powered delivery of multiple liquids. LCD printers are an inexpensive alternative for fabricating microfluidics, with minimal differences in fidelity and accuracy compared with a 40X more expensive DLP printer.</p>","PeriodicalId":22,"journal":{"name":"ACS Omega","volume":null,"pages":null},"PeriodicalIF":3.7,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsomega.4c07776","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142607985","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ACS OmegaPub Date : 2024-10-31DOI: 10.1021/acsomega.4c0674610.1021/acsomega.4c06746
Meron Getahun, Yonatan Nesru, Muktar Ahmed, Sunita Satapathy, Kebede Shenkute, Neeraj Gupta, Kero Jemal* and Mohammed Naimuddin*,
{"title":"Correction to “Phytochemical Composition, Antioxidant, Antimicrobial, Antibiofilm, and Antiquorum Sensing Potential of Methanol Extract and Essential Oil from Acanthus polystachyus Delile (Acanthaceae)”","authors":"Meron Getahun, Yonatan Nesru, Muktar Ahmed, Sunita Satapathy, Kebede Shenkute, Neeraj Gupta, Kero Jemal* and Mohammed Naimuddin*, ","doi":"10.1021/acsomega.4c0674610.1021/acsomega.4c06746","DOIUrl":"https://doi.org/10.1021/acsomega.4c06746https://doi.org/10.1021/acsomega.4c06746","url":null,"abstract":"","PeriodicalId":22,"journal":{"name":"ACS Omega","volume":null,"pages":null},"PeriodicalIF":3.7,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsomega.4c06746","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142609485","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ACS OmegaPub Date : 2024-10-31DOI: 10.1021/acsomega.4c0524710.1021/acsomega.4c05247
Maria Chiara Santangelo, Dalila Iacopini, Lucilla Favero, Riccardo Zecchi, Giuseppe Pieraccini, Sebastiano Di Pietro* and Valeria Di Bussolo*,
{"title":"One-Pot Stereospecific Synthesis of 1,4-Oligosaccharides by Glycal-Derived Vinyl Epoxides Assembly","authors":"Maria Chiara Santangelo, Dalila Iacopini, Lucilla Favero, Riccardo Zecchi, Giuseppe Pieraccini, Sebastiano Di Pietro* and Valeria Di Bussolo*, ","doi":"10.1021/acsomega.4c0524710.1021/acsomega.4c05247","DOIUrl":"https://doi.org/10.1021/acsomega.4c05247https://doi.org/10.1021/acsomega.4c05247","url":null,"abstract":"<p >Recently, naturally occurring linear 1,4-glycans have attracted remarkable attention for their activity in cancer and neurodegenerative disease treatment. Classical chemical synthetic strategies for linear 1,4-oligosaccharides are considerably time-consuming due to orthogonal protection/deprotection, the introduction of leaving groups, and various forms of activation of the glycosylation reaction. Herein, we present a new one-pot microwave-activated reiterative assembly of glycal-derived vinyl epoxides in an uncatalyzed substrate-dependent stereospecific process for the preparation of both β-1,4-<span>d</span>-Gulo and α-1,4-<span>d</span>-Manno oligosaccharides.</p>","PeriodicalId":22,"journal":{"name":"ACS Omega","volume":null,"pages":null},"PeriodicalIF":3.7,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsomega.4c05247","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142609729","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ACS OmegaPub Date : 2024-10-31DOI: 10.1021/acsomega.4c0850110.1021/acsomega.4c08501
Laurent Mosoni*, Arno Germond, Cécile Coudy-Gandilhon, Mélodie Malige, Agnès Claustre, Coralie Delabrise, Mehdi Djelloul-Mazouz, Yoann Delorme, Julien Hermet, Pierre Fafournoux, Lydie Combaret, Cécile Polge, Anne-Catherine Maurin and Daniel Taillandier*,
{"title":"Knockout of the Muscle-Specific E3 Ligase MuRF1 Affects Liver Lipid Metabolism upon Dexamethasone Treatment in Mice","authors":"Laurent Mosoni*, Arno Germond, Cécile Coudy-Gandilhon, Mélodie Malige, Agnès Claustre, Coralie Delabrise, Mehdi Djelloul-Mazouz, Yoann Delorme, Julien Hermet, Pierre Fafournoux, Lydie Combaret, Cécile Polge, Anne-Catherine Maurin and Daniel Taillandier*, ","doi":"10.1021/acsomega.4c0850110.1021/acsomega.4c08501","DOIUrl":"https://doi.org/10.1021/acsomega.4c08501https://doi.org/10.1021/acsomega.4c08501","url":null,"abstract":"<p >In order to preserve muscle mass during catabolic states, investigators are actively searching for a specific inhibitor of MuRF1, the only known E3 ligase that can target muscle contractile proteins for their degradation. However, what would be the consequences of such inhibitors on other organs, both in the short and long term? Indeed, skeletal muscles can provide amino acids for liver gluconeogenesis, which is a crucial adaptation for maintaining glucose homeostasis upon elevated energy demands (e.g., during prolonged starvation). Comparing 3-month-old wild-type and MuRF1-KO mice, we measured tissue weights, liver glycogen, lipid and protein content, and liver biochemical composition using Fourier transform infrared (FTIR) spectrometry in control animals and in dexamethasone (Dex)-treated animals. Dex induces a catabolic situation with muscle atrophy and lipid deposits in the liver. In response to Dex treatment, liver glycogen, lipid, and protein content increased in wild type (WT) and MuRF1-KO mice. We found that MuRF1 deletion differentially affected organ weights, the liver of KO mice being hypertrophied upon Dex treatment when compared to WT mice. Upon Dex treatment, muscle mass was preserved in MuRF1-KO mice, and by contrast, liver lipid content increased more in these animals than in WT mice. PLS-DA analysis of FTIR showed that the levels of 13 markers were significantly altered in KO vs WT mice, witnessing profound alterations of lipid, protein, and glycogen content in the liver due to the absence of MuRF1. Using Nile red and oil red lipid staining, we also found that both membrane-linked lipids and intracellular lipid droplets were altered due to the absence of MuRF1. Altogether, it seems that when the liver is deprived of the possibility of obtaining amino acids from muscle upon Dex treatment, there is a concomitant increase in tissue weight and anabolic activity.</p>","PeriodicalId":22,"journal":{"name":"ACS Omega","volume":null,"pages":null},"PeriodicalIF":3.7,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsomega.4c08501","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142609483","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ACS OmegaPub Date : 2024-10-31DOI: 10.1021/acsomega.4c0916510.1021/acsomega.4c09165
Panjaphong Lertsathitphong, Sarunputt Limpijumnong, Mithran Somasundrum, Anthony P. O’Mullane and Benchaporn Lertanantawong*,
{"title":"Electrochemical Formation of Pb Microwires with Tunable Morphology on Liquid Metal Electrodes","authors":"Panjaphong Lertsathitphong, Sarunputt Limpijumnong, Mithran Somasundrum, Anthony P. O’Mullane and Benchaporn Lertanantawong*, ","doi":"10.1021/acsomega.4c0916510.1021/acsomega.4c09165","DOIUrl":"https://doi.org/10.1021/acsomega.4c09165https://doi.org/10.1021/acsomega.4c09165","url":null,"abstract":"<p >Liquid metal electrodes based on Ga are an emerging area of interest given their fluid properties which can have significant impact on electrochemical processes. Here we study metal electrodeposition, namely lead electrodeposition on the liquid metal electrodes, gallium (Ga) and galinstan (GaInSn), which was performed in two different Pb<sup>2+</sup> electrolytes (PbCl<sub>2</sub> and Pb(NO<sub>3</sub>)<sub>2</sub>) to investigate any differences in the nature of the electrodeposit. Cyclic voltammetry and chronoamperometry were used to study the characteristics, kinetics, and nucleation and growth mechanisms of the electrodeposition process. Analysis of this electrochemical data, such as current density-time transients and diffusion coefficients under different potentials, revealed distinct behaviors for Pb deposition at each liquid metal and electrolyte, influencing the final morphology of the lead deposit. It was also found that the electrolyte concentration and deposition time were found to impact the morphology of the electrodeposited Pb. Scanning electron microscopy and energy dispersive X-ray spectroscopy revealed various types of Pb microstructures, including wire, branch-like, and flake-like formations, highlighting the differences in lead structural development when deposited on liquid gallium and Galinstan electrodes.</p>","PeriodicalId":22,"journal":{"name":"ACS Omega","volume":null,"pages":null},"PeriodicalIF":3.7,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsomega.4c09165","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142609484","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ACS OmegaPub Date : 2024-10-31DOI: 10.1021/acsomega.4c0697610.1021/acsomega.4c06976
Alexander Weiß*, Manuel Dutschke, Carla Vogt and Jan Zuber*,
{"title":"Determination of Binding Constants and Gas Phase Stabilities of Artificial Carbohydrate Receptor Complexes Using Electrospray Mass Spectrometry","authors":"Alexander Weiß*, Manuel Dutschke, Carla Vogt and Jan Zuber*, ","doi":"10.1021/acsomega.4c0697610.1021/acsomega.4c06976","DOIUrl":"https://doi.org/10.1021/acsomega.4c06976https://doi.org/10.1021/acsomega.4c06976","url":null,"abstract":"<p >In recent years, binding studies to determine complex stabilities and selectivities of artificial carbohydrate receptors with glycosides have been mainly performed using <sup>1</sup>H NMR, isothermal titration calorimetry (ITC), and other spectroscopic titration techniques. Native electrospray ionization (ESI) mass spectrometry is used only to verify the complex stoichiometries, although determination of dissociation constants is also possible. Herein, the binding of a 1,3,5-substituted 2,4,6-triethylbenzene-based receptor (CHR) to four alkyl-β-<span>d</span>-glucosides with varying alkyl side chain lengths (methyl (MGP), hexyl (HGP), octyl (OGP), and dodecyl (DGP)-β-<span>d</span>-glucosides), which was analyzed by ESI Fourier transform ion cyclotron resonance mass spectrometry (ESI-FT-ICR-MS) under optimized spray conditions in both ion modes, is reported. The complexes of the receptor with different sugars could be detected in 1:1 and 2:1 stoichiometries. Dissociation constants calculated for the 1:1 complexes showed a stability trend depending on the length of the alkyl side chain of the sugar: CHR:DGP > CHR:OGP > CHR:HGP > CHR:MGP. Gas phase stabilities determined by CID-MS confirm this relative trend in binding affinities. These findings substantiate the validity and applicability of ESI-MS as a method for investigating noncovalent complex stabilities and thus support research in the field of molecular recognition of carbohydrates by artificial receptors.</p>","PeriodicalId":22,"journal":{"name":"ACS Omega","volume":null,"pages":null},"PeriodicalIF":3.7,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsomega.4c06976","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142609280","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ACS OmegaPub Date : 2024-10-31DOI: 10.1021/acsomega.4c0277310.1021/acsomega.4c02773
Arumugam Ramu, and , Kannapiran Rajendrakumar*,
{"title":"Evaluation of the Role of [{Cu(PMDETA)}2(O22–)]2+ in Open-Air Photo ATRP of Methyl Methacrylate","authors":"Arumugam Ramu, and , Kannapiran Rajendrakumar*, ","doi":"10.1021/acsomega.4c0277310.1021/acsomega.4c02773","DOIUrl":"https://doi.org/10.1021/acsomega.4c02773https://doi.org/10.1021/acsomega.4c02773","url":null,"abstract":"<p >Herein, we report an open-air, photo accelerated atom transfer radical polymerization (ATRP) of methyl methacrylate (MMA) without employing any deoxygenating agent. Under open-air photo ATRP conditions, oxygen reversibly binds with [{Cu (PMDETA)}<sub>2</sub>(O<sub>2</sub><sup>2–</sup>)]<sup>2+</sup><b>(1)</b> to form the required activator, which was demonstrated by simple benchtop oxygen/nitrogen purging experiments. The binding mode of oxygen in <b>(1)</b> (μ(η<sup>2</sup>-η<sup>2</sup>) peroxo dicopper(II)) was investigated using UV Visible-NIR, FT-Raman and X-ray photoelectron (XPS) spectroscopic techniques. DFT studies and electrochemical measurements further support the catalytic role of <b>(1)</b> in open-air photo ATRP. With the synergistic involvement of Cu (II)Br<sub>2</sub>, PMDETA ligand and the intensity of light (365 nm, 4.2 mW cm<sup>–2</sup>), a well-controlled rapid polymerization of MMA under open-air condition was achieved (1.25< <i>Đ</i> < 1.47, 94% conversion in 200 min). The bromo chain end fidelity was exemplified by chain extension experiment, block copolymerization and MALDI-ToF analysis. Other monomers such as methyl acrylate, glycidyl methacrylate, and benzyl methacrylate were also polymerized under open-air condition with reasonable control over molecular weight and <i>Đ</i>. An open-air photo polymerization methodology would be fruitful for applications like photocurable printing, dental, optoelectronics, stereolithography, and protective coatings where simple but rapid photopolymerizations are desirable.</p>","PeriodicalId":22,"journal":{"name":"ACS Omega","volume":null,"pages":null},"PeriodicalIF":3.7,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsomega.4c02773","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142609728","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ACS OmegaPub Date : 2024-10-31DOI: 10.1021/acsomega.4c0788010.1021/acsomega.4c07880
Manzoor Ahmad, Andrew Muir and Matthew J. Langton*,
{"title":"Off–On Photo- and Redox-Triggered Anion Transport Using an Indole-Based Hydrogen Bond Switch","authors":"Manzoor Ahmad, Andrew Muir and Matthew J. Langton*, ","doi":"10.1021/acsomega.4c0788010.1021/acsomega.4c07880","DOIUrl":"https://doi.org/10.1021/acsomega.4c07880https://doi.org/10.1021/acsomega.4c07880","url":null,"abstract":"<p >A stimulus-responsive indole-based hydrogen bonding switch is reported, which enables off–on activation of transmembrane ion transport in response to photo- and redox triggers. This is achieved by alkylation of an indole-based anionophore, preorganized through intramolecular hydrogen bonding, with <i>o</i>-nitrobenzyl and azobenzene cages. This renders the anionophore inactive through formation of a six-membered intramolecular hydrogen bonding interaction and locking of the anion binding protons. Decaging with biologically relevant light and redox stimuli leads to efficient activation of anion transport across lipid bilayer membranes by unlocking the hydrogen bond donors, such that they are now available for anion binding and transport.</p>","PeriodicalId":22,"journal":{"name":"ACS Omega","volume":null,"pages":null},"PeriodicalIF":3.7,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsomega.4c07880","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142609415","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ACS OmegaPub Date : 2024-10-31DOI: 10.1021/acsomega.4c0869910.1021/acsomega.4c08699
Ze Kuang, Xiao-Bo Ding, Freda F. Li and Margaret A. Brimble*,
{"title":"Synthesis of the Spirocyclic Imine Fragment of Portimines Using a γ-Hydroxymethyl-α,β-butenolide Dienophile in a Diastereoselective Diels–Alder Reaction","authors":"Ze Kuang, Xiao-Bo Ding, Freda F. Li and Margaret A. Brimble*, ","doi":"10.1021/acsomega.4c0869910.1021/acsomega.4c08699","DOIUrl":"https://doi.org/10.1021/acsomega.4c08699https://doi.org/10.1021/acsomega.4c08699","url":null,"abstract":"<p >The synthesis of the spirocyclic imine fragment of the portimine family of marine toxins has been achieved. A densely functionalized key lactone-ester intermediate was assembled via a highly diastereoselective Diels–Alder cycloaddition, involving a novel γ-hydroxymethyl-α,β-butenolide dienophile. A Stille coupling was employed to install the vinyl group. Selective elaboration of the two carbonyl groups successfully afforded the spirocyclic imine fragment.</p>","PeriodicalId":22,"journal":{"name":"ACS Omega","volume":null,"pages":null},"PeriodicalIF":3.7,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsomega.4c08699","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142609482","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}