Helvetica Chimica Acta最新文献

筛选
英文 中文
The Two Janus Faces of CpRu-Based Deallylation Catalysts and Their Application for in Cellulo Prodrug Uncaging 基于 CpRu 的脱烯丙基催化剂的两面性及其在细胞内原药释放中的应用
IF 1.5 4区 化学
Helvetica Chimica Acta Pub Date : 2024-04-15 DOI: 10.1002/hlca.202400053
Alain Baiyoumy, Robin Vinck, Thomas R. Ward
{"title":"The Two Janus Faces of CpRu-Based Deallylation Catalysts and Their Application for in Cellulo Prodrug Uncaging","authors":"Alain Baiyoumy,&nbsp;Robin Vinck,&nbsp;Thomas R. Ward","doi":"10.1002/hlca.202400053","DOIUrl":"10.1002/hlca.202400053","url":null,"abstract":"<p>In the past 18 years, metal-catalyzed deallylation has proven a useful tool for studying biological processes <i>in cellulo</i> and in the early development of innovative therapeutic catalytic strategies. This reaction is catalyzed by Ru-piano stool complexes and has been reported to be compatible with air, water, and thiol-containing compounds such as glutathione. However, little is known about the true influence of biological components on the outcome of this reaction. The results presented herein reveal that the co-solvent used in the reaction affects the complex's stability and activity in air, while the presence of glutathione contributes to minimizing the formation of <i>N-</i>allylated by-products. In addition, we studied the effect of air on the Ru-catalyzed deallylation. Importantly, we found that, in the presence of air, the complex is deactivated and oxidizes glutathione into its disulfide.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 7","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202400053","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140572001","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
Controlled Release of Volatile Enones from Monomeric and Dimeric Thioether, Sulfoxide and Sulfone Profragrances 单体和二聚体硫醚、亚砜和砜类增殖体中挥发性烯酮的可控释放
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2024-04-10 DOI: 10.1002/hlca.202400046
Alain Trachsel, Sabine Leocata, Jean-Yves de Saint Laumer, Andreas Herrmann
{"title":"Controlled Release of Volatile Enones from Monomeric and Dimeric Thioether, Sulfoxide and Sulfone Profragrances","authors":"Alain Trachsel,&nbsp;Sabine Leocata,&nbsp;Jean-Yves de Saint Laumer,&nbsp;Andreas Herrmann","doi":"10.1002/hlca.202400046","DOIUrl":"10.1002/hlca.202400046","url":null,"abstract":"<p>Thioether (sulfide) profragrances are readily prepared by 1,4-addition of alkanethiols to enones (thia-<i>Michael</i> reaction). Under ambient conditions, they slowly release the parent enones, thus generating a long-lasting perfumery effect. The fragrance release of profragrances obtained by 1,4-addition of S, O and N nucleophiles to enones was compared on cotton and on a hard surface for monomeric and dimeric structures. To avoid the uncontrolled generation of volatile sulfur compounds from thioethers, we investigated the extent to which different side reactions occurred next to the expected formation of enones and alkanethiols. Headspace analyses on cotton showed that enones and aldehydes were the major reaction products, whereas none or only traces of β-mercaptoketones, diketones or alkanethiols were detected. The absence of alkanethiols indicated that 1,4-elimination of thioethers was not a major pathway for fragrance release. Extraction of the cotton sheets after analysis showed that thioethers were oxidised to sulfoxides, which then can generate enones by 1,4-elimination. Thioethers, sulfoxides and sulfones were shown to efficiently release enones in practical applications.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 6","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-04-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140571705","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
Total Synthesis of Core 3 & Core 4-Type Mucin Glycan Derivatives 核心 3 型和核心 4 型粘蛋白聚糖衍生物的全合成
IF 1.5 4区 化学
Helvetica Chimica Acta Pub Date : 2024-04-03 DOI: 10.1002/hlca.202400026
Carmen R. Cori, Rachel Hevey
{"title":"Total Synthesis of Core 3 & Core 4-Type Mucin Glycan Derivatives","authors":"Carmen R. Cori,&nbsp;Rachel Hevey","doi":"10.1002/hlca.202400026","DOIUrl":"10.1002/hlca.202400026","url":null,"abstract":"<p>Recent studies have demonstrated the ability of mucin O-glycans to attenuate virulence in diverse, cross-kingdom pathogens, sparking interest in their development as a novel therapeutic approach against infection. Although their virulence attenuating activity is evident, mucin glycans obtained from native sources comprise mixtures of several hundred distinct structures, and therefore the specific active glycan epitopes and molecular mechanisms of virulence attenuation remain unclear. Individual mucin glycan structures cannot be purified from native sources and are not amenable to automated synthesis; therefore, to further investigate the phenomena of virulence attenuation we have been developing convergent and scalable methods (&gt;30 mg per target glycan) to assemble a mucin O-glycan library in sufficient scale and purity to facilitate biological studies. Previously we described a method to obtain core 1 &amp; core 2-type mucin glycan derivatives that have since been used to identify active epitopes in <i>Candida albicans</i> and <i>Vibrio cholerae</i>. In the current study, we describe the expansion of our glycan library to include core 3 &amp; core 4-type derivatives, increasing the structural diversity of our platform for biological evaluation.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 7","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202400026","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140571667","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 of N-Substituted Pyrrole-2,5-dicarboxylic Acids from Pyrroles 从吡咯合成 N-取代的吡咯-2,5-二羧酸
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2024-04-03 DOI: 10.1002/hlca.202400036
Jan-Simon Jeshua Friedrichs, Dr. Luca Schmermund, Dr. Corinna Urmann, Prof. Dr. Volker Sieber
{"title":"Synthesis of N-Substituted Pyrrole-2,5-dicarboxylic Acids from Pyrroles","authors":"Jan-Simon Jeshua Friedrichs,&nbsp;Dr. Luca Schmermund,&nbsp;Dr. Corinna Urmann,&nbsp;Prof. Dr. Volker Sieber","doi":"10.1002/hlca.202400036","DOIUrl":"10.1002/hlca.202400036","url":null,"abstract":"<p>Pyrrole-2,5-dicarboxylic acid (PDCA) is a heterocyclic aromatic dicarboxylic acid that may emerge as a new monomer for polyester production. Compared to its structurally related and bio-based furan-2,5-dicarboxylic acid (FDCA) that is already used for the production of polyethylene furanoate (PEF), PDCA shows excellent potential as its nitrogen can be targeted for further derivatization, thus enabling tuning of the properties of a PDCA containing polymer. In light of this, we recognized the need to explore efficient synthetic approaches for producing PDCAs in high yields. Here, we report a five-step synthesis route for <i>N</i>-substituted PDCAs starting from pyrrole, with total yields up to 42 %. The synthetic approach allowed the introduction of several different functional moieties to the pyrrole nitrogen, such as aliphatic saturated and unsaturated side-chains, as well as benzylic groups.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":"107 6","pages":""},"PeriodicalIF":1.8,"publicationDate":"2024-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202400036","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140571700","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
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
0
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
相关产品
×
本文献相关产品
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信