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Introduction for the Special Collection of Papers in the Honor of the President of the 56th Bürgenstock Conference, Alois Fürstner 第 56 届比尔根山会议主席 Alois Fürstner 纪念论文集导言
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2024-03-29 DOI: 10.1002/hlca.202400042
Prof. Alois Fürstner
{"title":"Introduction for the Special Collection of Papers in the Honor of the President of the 56th Bürgenstock Conference, Alois Fürstner","authors":"Prof. Alois Fürstner","doi":"10.1002/hlca.202400042","DOIUrl":"10.1002/hlca.202400042","url":null,"abstract":"<p>\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 5","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-03-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202400042","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140367343","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Isolation of Fidaxomicin and Shunt Metabolites from Actinoplanes deccanensis 从 Actinoplanes deccanensis 中分离出菲达霉素和分流代谢物
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2024-03-20 DOI: 10.1002/hlca.202400013
Erik Jung, Dr. Maja Hunter, Dr. Andrea Dorst, Alexander Major, Tatjana Teofilovic, Prof. Dr. Rolf Müller, Prof. Dr. Karl Gademann
{"title":"Isolation of Fidaxomicin and Shunt Metabolites from Actinoplanes deccanensis","authors":"Erik Jung,&nbsp;Dr. Maja Hunter,&nbsp;Dr. Andrea Dorst,&nbsp;Alexander Major,&nbsp;Tatjana Teofilovic,&nbsp;Prof. Dr. Rolf Müller,&nbsp;Prof. Dr. Karl Gademann","doi":"10.1002/hlca.202400013","DOIUrl":"10.1002/hlca.202400013","url":null,"abstract":"<p>A protocol for the isolation of the antibiotic fidaxomicin (Fdx) from <i>Actinoplanes deccanensis</i> and the isolation of shunt metabolites from <i>A. deccanensis fdxG2</i><sup><i>−</i></sup> is reported. We constructed the mutant strain <i>A. deccanensis fdxG2</i><sup><i>−</i></sup> by genetic manipulation which enabled the isolation of shunt metabolites as useful starting points for semisynthetic analogues of Fdx. Furthermore, a synthetic protocol for the conversion of complex <i>A. deccanensis fdxG2</i><sup><i>−</i></sup> extracts into the single compound FdxG2-OH <i>via</i> methanolysis is presented. This synthetic procedure is complemented by images and practical notes. Full structure assignment is given in the SI and the characterization data files are published to aid experimentalists. The protocol is also suitable as an undergraduate laboratory project. We hope to facilitate research into new Fdx derivatives through the availability of this procedure.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 5","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202400013","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140202233","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Cover Picture: (Helv. Chim. Acta 3/2024) 封面图片： (Helv. Chim. Acta 3/2024)
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2024-03-15 DOI: 10.1002/hlca.202470301
{"title":"Cover Picture: (Helv. Chim. Acta 3/2024)","authors":"","doi":"10.1002/hlca.202470301","DOIUrl":"https://doi.org/10.1002/hlca.202470301","url":null,"abstract":"<p>\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 3","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202470301","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140135357","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Does the Central Nitrogen Atom Make a Difference? A Comparison of Non-Coordinating Pyridine and Benzene Spacers in Multitopic Ligands 中心氮原子有区别吗？多位配体中的非配位吡啶和苯间隔的比较
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2024-03-14 DOI: 10.1002/hlca.202400023
Catherine E. Housecroft, Edwin C. Constable
{"title":"Does the Central Nitrogen Atom Make a Difference? A Comparison of Non-Coordinating Pyridine and Benzene Spacers in Multitopic Ligands","authors":"Catherine E. Housecroft,&nbsp;Edwin C. Constable","doi":"10.1002/hlca.202400023","DOIUrl":"10.1002/hlca.202400023","url":null,"abstract":"<p>In metal coordination compounds of the divergent ligands 4,2′:6′,4“-terpyridine and 3,2′:6′,3”-terpyridine and their 4′-functionalized derivatives, the central pyridine ring of the 4,2′:6′,4“-terpyridine and 3,2′:6′,3”-terpyridine domains is non-coordinated. We present an overview of data from the Cambridge Structural Database to assess whether there are structural similarities between the coordination compounds of 4,2′:6′,4“-tpy and 1,3-di(pyridin-4-yl)benzene, and between 3,2′:6′,3”-tpy and 1,3-di(pyridin-3-yl)benzene. Based upon structurally characterized compounds, it emerges that the coordination chemistry of ligands including one or more 4,2′:6′,4“-terpyridine or 3,2′:6′,3”-terpyridine metal-binding domains is more abundantly exemplified than that of corresponding ligands based upon 1,3-di(pyridin-4-yl)benzene and 1,3-di(pyridin-3-yl)benzene. We provide an overview of metallamacrocycles and cages, 1D-coordination polymers and 2D- and 3D-networks.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 5","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-03-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140150151","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Submonomer Synthesis of Inverse Polyamidoamine (i-PAMAM) Dendrimer Antibacterials 反式聚氨基胺（i-PAMAM）树枝状聚合物抗菌剂的亚单体合成
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2024-03-14 DOI: 10.1002/hlca.202400041
Hippolyte Personne, Xiaoling Hu, Etienne Bonvin, Jérémie Reusser, Jean-Louis Reymond
{"title":"Submonomer Synthesis of Inverse Polyamidoamine (i-PAMAM) Dendrimer Antibacterials","authors":"Hippolyte Personne,&nbsp;Xiaoling Hu,&nbsp;Etienne Bonvin,&nbsp;Jérémie Reusser,&nbsp;Jean-Louis Reymond","doi":"10.1002/hlca.202400041","DOIUrl":"10.1002/hlca.202400041","url":null,"abstract":"<p>Herein we report that the submonomer method for peptoid synthesis enables access to pure i-PAMAM dendrimers up to 16 amino termini by a divergent solid-phase synthesis using the inexpensive bis(3-trifluoroacetamidopropyl)amine as branching unit. We exemplify this new and efficient approach by a structure-activity relationship study of antibacterial dendrimers obtained by appending the polycationic i-PAMAM dendrimer to a hydrophobic core consisting of either an oligoleucine peptide or an oligo-<i>N</i>-isobutylglycine peptoid. These non-hemolytic dendrimers kill Gram-negative bacteria such as <i>Pseudomonas aeruginosa, Acinetobacter baumannii</i> and <i>Escherichia coli</i> as well as the Gram-positive methicillin-resistant <i>Staphylococcus aureus</i> (MRSA) by a non-membrane disruptive mechanism involving aggregation of intracellular content as reported for antimicrobial peptoids.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 5","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-03-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202400041","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140150144","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Protocol for the Photocatalytic Hydroxyalkenylation of Alkenes Using 1,2-Bis(phenylsulfonyl)ethylene and Water 使用 1,2-双（苯磺酰基）乙烯和水对烯烃进行光催化羟基烯化反应的规程
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2024-03-13 DOI: 10.1002/hlca.202400017
Chen-Yang Tsai, Chun-Yu Chen, Yen-Ku Wu, Ilhyong Ryu
{"title":"Protocol for the Photocatalytic Hydroxyalkenylation of Alkenes Using 1,2-Bis(phenylsulfonyl)ethylene and Water","authors":"Chen-Yang Tsai,&nbsp;Chun-Yu Chen,&nbsp;Yen-Ku Wu,&nbsp;Ilhyong Ryu","doi":"10.1002/hlca.202400017","DOIUrl":"10.1002/hlca.202400017","url":null,"abstract":"<p>We report on a protocol for the hydroxyalkenylation of alkenes using an acridinium photoredox catalyst in combination with 1,2-bis(phenylsulfonyl)ethylene and water. Using the protocol, alkenes could be converted into the corresponding 1-phenylsulfonyl-4-hydroxyalkenes in good yields. The hydroxyalkenylation involves the nucleophilic hydroxylation of alkene-derived radical cations to give β-hydroxyalkyl radicals, which then undergo a radical addition/β-elimination sequence. The catalytic cycle is likely sustained by electron transfer from the acridine radical to the benzenesulfonyl radical, which is formed via a radical addition/elimination sequence.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 5","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-03-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140128197","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A Targeted Approach for the Metabolome Analysis of E. coli Biofilms 分析大肠杆菌生物膜代谢组的靶向方法
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2024-03-08 DOI: 10.1002/hlca.202300240
Jan Rockstroh, Sandy Gerschler, Nadin Schultze, Christian Schulze, Martina Wurster, Karen Methling, Sebastian Guenther, Michael Lalk
{"title":"A Targeted Approach for the Metabolome Analysis of E. coli Biofilms","authors":"Jan Rockstroh,&nbsp;Sandy Gerschler,&nbsp;Nadin Schultze,&nbsp;Christian Schulze,&nbsp;Martina Wurster,&nbsp;Karen Methling,&nbsp;Sebastian Guenther,&nbsp;Michael Lalk","doi":"10.1002/hlca.202300240","DOIUrl":"10.1002/hlca.202300240","url":null,"abstract":"<p>Biofilms of pathogenic bacteria are responsible for persistent infections in humans, therefore investigations of biofilm formation and treatment strategies are required. The gram-negative enterobacterium <i>Escherichia (E.) coli</i> is the most common pathogen causing chronic or recurring urinary tract infections. Metabolomics approaches targeted the bacterium to investigate specific metabolic patterns of biofilms and regulatory influences on biofilm formation. In this study, we aimed to investigate the metabolome of biofilms formed by the multidrug-resistant extended-spectrum beta-lactamase-producing (ESBL) <i>E. coli</i> PBIO729. For this purpose, a protocol for fast sampling of the macrocolony biofilms and efficient extraction of metabolites was optimized. Validation of an LC-MS/MS method confirmed its usability for the analysis of nucleotides and other phosphorylated metabolites. A GC-MS approach was used to monitor nutrient uptake from the medium in addition to the analysis of amino acid content and metabolites of glycolysis and TCA cycle in <i>E. coli</i> biofilms.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 6","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-03-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202300240","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140074675","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A Fluorogenic Substrate for Quinoline Reduction: Pnictogen-Bonding Catalysis in Aqueous Systems 喹啉还原的含氟底物： 水溶液体系中的双键催化作用
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2024-03-06 DOI: 10.1002/hlca.202400015
Giacomo Renno, Qing-Xia Zhang, Antonio Frontera, Naomi Sakai, Stefan Matile
{"title":"A Fluorogenic Substrate for Quinoline Reduction: Pnictogen-Bonding Catalysis in Aqueous Systems","authors":"Giacomo Renno,&nbsp;Qing-Xia Zhang,&nbsp;Antonio Frontera,&nbsp;Naomi Sakai,&nbsp;Stefan Matile","doi":"10.1002/hlca.202400015","DOIUrl":"10.1002/hlca.202400015","url":null,"abstract":"<p>It is often said that pnictogen-bonding catalysis, and <i>σ</i>-hole catalysis in general, would not work in aqueous systems because the solvent would interfere as an overcompetitive pnictogen-bond acceptor. In this study, we show that the transfer of pnictogen-bonding catalysis from hydrophobic solvents to aqueous systems is possible by replacing only hydrophobic with hydrophilic substrates, without changing catalyst or reaction. This differs from conventional covalent <i>Lewis</i> acid catalysts, which are instantaneously destroyed by ligand exchange. With their water-proof substituents in place of exchangeable ligands, pnictogen-bonding catalysts, the supramolecular counterpart of <i>Lewis</i> acid catalysts, are evinced to catalyze transfer hydrogenation of quinolines in neutral aqueous systems. To secure these results, we introduce a water-soluble fluorogenic substrate that releases a coumarin upon the reduction of quinolines instead of activated quinolidiniums, and stiborane catalysts with deepened <i>σ</i> holes. They demonstrate that pnictogen-bonding catalysts can operate in higher-order architectures for supramolecular systems catalysis under biologically relevant conditions, and provide an operational assay for high-throughput catalyst screening by fluorescence imaging, in situ under relevant aqueous conditions.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 5","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202400015","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140045446","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Organocatalytic Enantioselective Synthesis of Chiral Spiro-indoline-pyrazolones through a formal [4+1] Annulation Reaction of 4-Bromopyrazolones and aza-ortho-Quinone Methides 通过 4-溴吡唑酮和氮杂北喹酮甲苷的正式 [4+1] 嵌合反应，有机催化对映体选择性合成手性螺吲哚啉吡唑酮
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2024-03-06 DOI: 10.1002/hlca.202400029
Laura Carceller-Ferrer, Carlos Rodríguez-Arias, Marc Montesinos-Magraner, Amparo Sanz-Marco, Judit Hostalet-Romero, Gonzalo Blay, José R. Pedro, Carlos Vila
{"title":"Organocatalytic Enantioselective Synthesis of Chiral Spiro-indoline-pyrazolones through a formal [4+1] Annulation Reaction of 4-Bromopyrazolones and aza-ortho-Quinone Methides","authors":"Laura Carceller-Ferrer,&nbsp;Carlos Rodríguez-Arias,&nbsp;Marc Montesinos-Magraner,&nbsp;Amparo Sanz-Marco,&nbsp;Judit Hostalet-Romero,&nbsp;Gonzalo Blay,&nbsp;José R. Pedro,&nbsp;Carlos Vila","doi":"10.1002/hlca.202400029","DOIUrl":"10.1002/hlca.202400029","url":null,"abstract":"<p>In this communication, a straighforward asymmetric synthesis of spiro-indoline-pyrazolone compounds is described. This methodology consists in a formal [4+1] cycloaddition reaction of 4-bromopyrazolones and aza-<i>ortho</i>-quinone methides generated <i>in situ</i> catalyzed by a bisquinine-derived squaramide in CHCl<sub>3</sub> under basic conditions. A variety of chiral spirocyclic compounds bearing a pyrazolone and an indoline moieties were obtained in moderate to good yields (up to 68 %) and moderate to excellent enantioselectivities (up to 93 % ee).</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 4","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202400029","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140054341","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Manganese-Mediated Synthesis of NHC-Phosphine Ligand Precursors 锰介导的 NHC-膦配体前体合成
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2024-03-05 DOI: 10.1002/hlca.202400009
Jérémy Willot, Sana Fatima, Carine Duhayon, Noël Lugan, Yves Canac, Dmitry A. Valyaev
{"title":"Manganese-Mediated Synthesis of NHC-Phosphine Ligand Precursors","authors":"Jérémy Willot,&nbsp;Sana Fatima,&nbsp;Carine Duhayon,&nbsp;Noël Lugan,&nbsp;Yves Canac,&nbsp;Dmitry A. Valyaev","doi":"10.1002/hlca.202400009","DOIUrl":"10.1002/hlca.202400009","url":null,"abstract":"<p>Alkylation of <i>N</i>-substituted imidazoles ImR’ (R’=2,4,6-trimethylphenyl, 2,6-diisopropylphenyl, 1-adamantyl) with Mn(I) methylenephosphonium complexes [Cp(CO)<sub>2</sub>Mn(η<sup>2</sup>-<i>P,C</i>-R<sub>2</sub>P=C(H)Ph)](BF<sub>4</sub>) (PR<sub>2</sub>=PPh<sub>2</sub>, PCy<sub>2</sub>, <i>trans</i>-P<span>C(H)PhCH<sub>2</sub>CH<sub>2</sub>C</span> (H)Ph) followed by photochemical demetallation afforded a series of bidentate NHC-phosphine ligand precursors [R<sub>2</sub>PC(H)PhImR’](BF<sub>4</sub>) in moderate to good yield. The same strategy was successfully applied to <i>N</i>-functionalized imidazoles ImL (L=2-pyridyl, CH<sub>2</sub>SMe, CH<sub>2</sub>ImMe) to afford selectively NHC core pincer pre-ligands featuring phosphine/thioether, phosphine/NHC and phosphine/pyridine side arms. For PCy<sub>2</sub> derivatives, free NHCs in both bidentate and pincer series generated by deprotonation of the corresponding cationic precursors were shown to be persistent at room temperature.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 4","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-03-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140045512","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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