Helvetica Chimica Acta最新文献_第5页

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, Sandy Gerschler, Nadin Schultze, Christian Schulze, Martina Wurster, Karen Methling, Sebastian Guenther, Michael Lalk","doi":"10.1002/hlca.202300240","DOIUrl":"10.1002/hlca.202300240","url":null,"abstract":"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 Escherichia (E.) coli 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) E. coli 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 E. coli biofilms.","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"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

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

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, Qing-Xia Zhang, Antonio Frontera, Naomi Sakai, Stefan Matile","doi":"10.1002/hlca.202400015","DOIUrl":"10.1002/hlca.202400015","url":null,"abstract":"It is often said that pnictogen-bonding catalysis, and σ-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 Lewis 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 Lewis 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 σ 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.","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"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

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

引用次数: 0

Evolution of the Manufacturing Route towards a Key Benzothiophen-2-yl-Boronic Acid Building Block of Rogaratinib 罗加替尼的关键苯并噻吩-2-基硼酸结构单元生产工艺的演变

IF 1.8 4区化学

Helvetica Chimica Acta Pub Date : 2024-03-04 DOI: 10.1002/hlca.202400008

Jörg Gries, Johannes Platzek, Holger Paulsen

{"title":"Evolution of the Manufacturing Route towards a Key Benzothiophen-2-yl-Boronic Acid Building Block of Rogaratinib","authors":"Jörg Gries, Johannes Platzek, Holger Paulsen","doi":"10.1002/hlca.202400008","DOIUrl":"10.1002/hlca.202400008","url":null,"abstract":"The evolution of the synthesis of a benzothiophene-2-yl-boronic acid - a key building block for the anti-cancer agent Rogaratinib - is reported from multi-gram scale to industrialization. The pitfalls and learnings during process development are outlined, describing the optimization of the initial research synthesis route, investigation of an alternative approach based on a palladium-catalyzed Newman-Kwart rearrangement and finally changing the synthetic strategy from thiophene-construction to benzene-ring formation. Although the initial route was utilized to deliver material on kg-scale, the requirements for market-supply triggered the decision to pursue a new synthetic route. Catalyst costs, high purity-requirements, and not the least technical practicality caused the change to a synthesis with indeed higher step-count. However, this could be mitigated by repeated application of a telescoping approach. The free boronic acid was finally selected and manufactured as a stable isolated intermediate after challenges like proto-deboronation and trimerization to boroxine upon drying could be solved by an optimized crystallization procedure.","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2024-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202400008","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140033867","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

Murielle F. Delley Murielle F. Delley

IF 1.8 4区化学

Helvetica Chimica Acta Pub Date : 2024-02-29 DOI: 10.1002/hlca.202400019

引用次数: 0

Revealing the Indispensable Role of the RFamide Functionality using a Novel Acid Labile Benzofuranone based Amine (ALBA) Linker 使用新型易酸苯并呋喃酮胺 (ALBA) 连接剂揭示 RFamide 功能的重要作用

IF 1.8 4区化学

Helvetica Chimica Acta Pub Date : 2024-02-25 DOI: 10.1002/hlca.202300204

Gemma Mudd, Megan Hendrikse, Steven Shave, Douglas R Houston, Robert P Millar, Manfred Auer

{"title":"Revealing the Indispensable Role of the RFamide Functionality using a Novel Acid Labile Benzofuranone based Amine (ALBA) Linker","authors":"Gemma Mudd, Megan Hendrikse, Steven Shave, Douglas R Houston, Robert P Millar, Manfred Auer","doi":"10.1002/hlca.202300204","DOIUrl":"10.1002/hlca.202300204","url":null,"abstract":"The RFamide family of peptides represents an important class of GPCR ligand neuropeptides covering a wide range of biological functions. While many analogues of the highly conserved C-terminal RFamide motif within this peptide class have been synthesized and their functional significance elucidated, additional exploration of the structure activity relationship is of value. We have developed a novel linker for solid phase peptide synthesis (SPPS) which is able to anchor amine functionalised compounds for further elaboration. The acid labile benzofuranone based amine (ALBA) linker (5-(3-aminopropylcarbamoyl)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]benzoic acid) is compatible with Fmoc based SPPS and has two cleavage modes. As a proof of concept, the ALBA linker was used to successfully synthesise a novel analogue of Kisspeptin 10, the natural ligand for GPCR54, whereby the natural RFamide motif was replaced with an RFamine. Biological evaluation of the amine-containing analogue revealed that the group is not compatible with receptor activation.","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2024-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202300204","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139968805","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

Synthesis and Quantitative Analysis of Glycans Conjugated to Gold Nanoparticles 与金纳米粒子共轭的聚糖的合成与定量分析

IF 1.8 4区化学

Helvetica Chimica Acta Pub Date : 2024-02-20 DOI: 10.1002/hlca.202300209

Kuo-Shiang Liao, Chih-Chuan Kung, Li-Chun Cheng, Cinya Chung, Chi-Huey Wong

{"title":"Synthesis and Quantitative Analysis of Glycans Conjugated to Gold Nanoparticles","authors":"Kuo-Shiang Liao, Chih-Chuan Kung, Li-Chun Cheng, Cinya Chung, Chi-Huey Wong","doi":"10.1002/hlca.202300209","DOIUrl":"10.1002/hlca.202300209","url":null,"abstract":"Nanoparticles, especially gold nanoparticles (GNPs) have emerged as promising tools for biomedical applications due to their unique properties and ability to be functionalized. However, quantitative analysis of biomolecules conjugated to nanoparticles remains a challenge. Here we report a method to conjugate a synthetic hybrid-type N-glycan to GNPs and quantitatively analyze the glycan content. The glycan was first conjugated to N-hydroxysuccinimide (NHS)-ester activated GNPs and confirmed qualitatively by Fourier-transform infrared spectroscopy and flow cytometry. The glycan conjugated-GNPs were then treated with neuraminidase to release terminal sialic acid from the glycan, which was labeled with 1,2-diamino-4,5-methylenedioxybenzene and quantitatively analyzed by Ultraperformance Liquid Chromatography (UPLC). The amount of the sialic acid released was equivalent to the glycan content on GNPs. This method enabled a precise quantification of glycans conjugated to gold nanoparticles and should facilitate its biomedical applications, including studies of multivalent receptor-glycan interaction, cell targeting and sorting, and immunization. Overall, this work provides an effective approach to synthesize and characterize nanoparticles conjugates.","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2024-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139953814","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

Andrea Vasella and the Active Site of Glycoside Hydrolases Andrea Vasella 和糖苷水解酶的活性位点

IF 1.8 4区化学

Helvetica Chimica Acta Pub Date : 2024-02-19 DOI: 10.1002/hlca.202300194

Roland Hoos-Michelotti

引用次数: 0

Cover Picture: (Helv. Chim. Acta 2/2024) 封面图片： (Helv. Chim. Acta 2/2024)

IF 1.8 4区化学

Helvetica Chimica Acta Pub Date : 2024-02-15 DOI: 10.1002/hlca.202470201

引用次数: 0