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Cover Picture: (Helv. Chim. Acta 10/2023) 封面图片：（Helv.Chim.Acta 10/2023）
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2023-10-19 DOI: 10.1002/hlca.202371001
{"title":"Cover Picture: (Helv. Chim. Acta 10/2023)","authors":"","doi":"10.1002/hlca.202371001","DOIUrl":"https://doi.org/10.1002/hlca.202371001","url":null,"abstract":"<p>\u0000 \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":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2023-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202371001","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"50137935","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
Kilogram-Scale Synthesis of 4-Chloro-6-(6-methoxypyridin- 3-yl)pyrimidine through a Suzuki–Miyaura Cross-Coupling Using Micellar Catalysis 利用胶束催化通过Suzuki-Miyaura交叉偶联合成4 -氯- 6 -(6 -甲氧基吡啶- 3 -基)嘧啶
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2023-10-18 DOI: 10.1002/hlca.202300143
Nicholas A. Isley, Fabrice Gallou
{"title":"Kilogram-Scale Synthesis of 4-Chloro-6-(6-methoxypyridin- 3-yl)pyrimidine through a Suzuki–Miyaura Cross-Coupling Using Micellar Catalysis","authors":"Nicholas A. Isley,&nbsp;Fabrice Gallou","doi":"10.1002/hlca.202300143","DOIUrl":"10.1002/hlca.202300143","url":null,"abstract":"<p>A scalable and environmentally benign protocol for a Suzuki–Miyaura cross-coupling in water using vitamin E derived surfactant TPGS-750-M is reported. The protocol is the most simple and standard for such transformations under micellar catalysis that has been amply utilized within our own research and development portfolio over the last decade. The impact of the synthetic procedure is reenforced by green Process Mass Intensity and Total Carbon Release metrics.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2023-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202300143","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135888016","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
Optimizing Phosphate Couplings for Dolichyl Diphosphochitobiose to Enable Protein N-Glycosylation Studies 优化二羟基二磷酸亚甲基双糖的磷酸盐偶联物，促进蛋白质 N-糖基化研究
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2023-10-13 DOI: 10.1002/hlca.202300171
Matheus A. Meirelles, Jean-Louis Reymond
{"title":"Optimizing Phosphate Couplings for Dolichyl Diphosphochitobiose to Enable Protein N-Glycosylation Studies","authors":"Matheus A. Meirelles,&nbsp;Jean-Louis Reymond","doi":"10.1002/hlca.202300171","DOIUrl":"10.1002/hlca.202300171","url":null,"abstract":"<p>Herein we report an optimized synthesis for dolichyl diphosphochitobiose (GlcNAc<sub>2</sub>-PP-Dol<sub>25</sub>), a probe useful for biochemical and structural studies of protein <i>N</i>-glycosylation in eukaryotic cells. We improved three phosphate coupling steps in terms of yields and reaction times, namely chitobiose phosphorylation, dolichol phosphorylation, and phosphate-phosphate coupling, by adjusting reagents and conditions. We also developed an efficient preparative reverse-phase HPLC purification protocol followed by ion exchange step to obtain the pure product as a stable sodium salt. These optimized procedures ensure a reliable supply of GlcNAc<sub>2</sub>-PP-Dol<sub>25</sub> for enzymatic studies.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2023-10-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134993755","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
Development of a 2nd Generation Process for 3-Ethyl-4-Hydroxy-5-Methylbenzonitrile – A Key Building Block of S1P1 Receptor Modulator Cenerimod – through a Non-Classical Nitrile Formation Using Hydroxylamine-O-sulfonic Acid (HOSA) 利用羟胺-O-磺酸 (HOSA) 通过非典型腈形成法开发 S1P1 受体调节剂塞内莫德的关键结构单元--3-乙基-4-羟基-5-甲基苯腈的第二代工艺
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2023-10-11 DOI: 10.1002/hlca.202300167
Gabriel Schäfer, Tony Fleischer
{"title":"Development of a 2nd Generation Process for 3-Ethyl-4-Hydroxy-5-Methylbenzonitrile – A Key Building Block of S1P1 Receptor Modulator Cenerimod – through a Non-Classical Nitrile Formation Using Hydroxylamine-O-sulfonic Acid (HOSA)","authors":"Gabriel Schäfer,&nbsp;Tony Fleischer","doi":"10.1002/hlca.202300167","DOIUrl":"10.1002/hlca.202300167","url":null,"abstract":"<p>A new, improved 2nd generation route for the synthesis of 3-ethyl-4-hydroxy-5-methylbenzonitrile has been developed. The original route started from 2-ethyl-6-methylaniline, which was converted by a classical sequence of <i>para</i>-bromination, cyanation and Sandmeyer hydroxylation into the desired phenol. This route was used on multi-kg scale and delivered the product with the desired purity. However, the route was not ideal, as it featured safety critical steps (cyanation), employed undesirable solvents (DMF), included laborious workup and isolation procedures, and suffered from a low overall yield (40–45 %) and suboptimal green metrics (PMI: 210). We envisioned a new, non-classical approach to the product by introducing the nitrile through a <i>para</i>-selective formylation, followed by transformation of the intermediate aldehyde into the nitrile with hydroxylamine-<i>O</i>-sulfonic acid (HOSA). The new sequence of Sandmeyer hydroxylation, Duff formylation and HOSA-promoted nitrile formation was thoroughly optimized and finally scaled up to 400 g. This novel 3-step sequence delivered 3-ethyl-4-hydroxy-5-methylbenzonitrile in 69 % overall yield with excellent purity (99.3 % a/a) and a vastly improved PMI of 81.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2023-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202300167","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136208566","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 Robert Deschenaux. 为纪念罗伯特·德舍诺的特别文集简介。
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2023-10-04 DOI: 10.1002/hlca.202300168
Jean-François Nierengarten, Jean-Marie Lehn
{"title":"Introduction for the Special Collection of Papers in the Honor of Robert Deschenaux.","authors":"Jean-François Nierengarten,&nbsp;Jean-Marie Lehn","doi":"10.1002/hlca.202300168","DOIUrl":"10.1002/hlca.202300168","url":null,"abstract":"<p>\u0000 \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":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2023-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202300168","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135590942","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
iso-Fatty Acid Metabolism in Caenorhabditis elegans’ Ceramide Biosynthesis 秀丽隐杆线虫神经酰胺生物合成中的异脂肪酸代谢
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2023-10-02 DOI: 10.1002/hlca.202300131
Rocío Rivera Sánchez, Siva Bandi, Marie-Désirée Scheidt, Hanna Laaroussi, Bennett William Fox, Yojiro Ishida, Gaétan Glauser, Sylvain Sutour, Stephan H. von Reuss
{"title":"iso-Fatty Acid Metabolism in Caenorhabditis elegans’ Ceramide Biosynthesis","authors":"Rocío Rivera Sánchez,&nbsp;Siva Bandi,&nbsp;Marie-Désirée Scheidt,&nbsp;Hanna Laaroussi,&nbsp;Bennett William Fox,&nbsp;Yojiro Ishida,&nbsp;Gaétan Glauser,&nbsp;Sylvain Sutour,&nbsp;Stephan H. von Reuss","doi":"10.1002/hlca.202300131","DOIUrl":"10.1002/hlca.202300131","url":null,"abstract":"<p>Ceramide biosynthesis and its connection to iso-fatty acid metabolism in the model organism <i>Caenorhabditis elegans</i> was investigated using a combination of reverse genetics and comparative ESI-(+)-HR-MS<sup>e</sup> ceramide profiling along with incorporation experiments with bacterial mutants specifically enriched with isotopically labeled branched-chain amino acids or branched-chain fatty acids. Incorporation of a <span>l</span>-leucine-derived isovalerate unit into the conserved d17 : 1iso sphingosine building block proceeds through <i>elo-5</i> dependent chain elongation and depends on peroxisomal β-oxidation by the 3-ketoacyl-CoA thiolase <i>daf-22</i>, although ceramide profiles of N2 wildtype and <i>daf-22(ok693)</i> are indistinguishable. Biosynthesis of the homologous <i>N</i>-iso-acyl moieties also depends on <span>l</span>-leucine and isovalerate chain elongation but proceeds independently of <i>elo-5</i> and <i>daf-22</i>. Biosynthesis of the dominating <i>N</i>-docosanoyl moiety depends on <i>elo-3-</i>catalyzed chain elongation of bacteria-derived palmitic acid, whereas the <i>N</i>-tetracosanoyl moiety is derived from <i>de novo</i> lipogenesis.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2023-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202300131","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135805190","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
Enantio- and Diastereoselective (Ipc)2BOTf-Mediated Aldol Reactions of Morpholine Carboxamides 对映体和非对映体选择性 (Ipc)2BOTf 介导的吗啉羧酰胺醛醇反应
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2023-09-29 DOI: 10.1002/hlca.202300126
Lee Pedzisa, Andrii Monastyrskyi, Camille D. Parker, William R. Roush
{"title":"Enantio- and Diastereoselective (Ipc)2BOTf-Mediated Aldol Reactions of Morpholine Carboxamides","authors":"Lee Pedzisa,&nbsp;Andrii Monastyrskyi,&nbsp;Camille D. Parker,&nbsp;William R. Roush","doi":"10.1002/hlca.202300126","DOIUrl":"10.1002/hlca.202300126","url":null,"abstract":"<p>Highly enantio- and diastereoselective (Ipc)<sub>2</sub>BOTf mediated aldol reactions of morpholine carboxamides are described. A wide variety of α-substituted <i>N</i>-acyl morpholine carboxamides were successfully employed, including α-bromo, α-chloro, α-vinyl and <i>para-</i>methoxyphenyl morpholine carboxamides which provided the corresponding aldol products in moderate to excellent yields, and generally with high enantio- and diastereoselectivities.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2023-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202300126","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135132429","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 {CB11} Monocarborane Sulfonamides by B2-Selective Rhodium-Catalyzed B−H Activation B2选择性铑催化B-H活化合成{CB11}单碳硼烷磺酰胺
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2023-09-28 DOI: 10.1002/hlca.202300144
Zehua Ye, Jizeng Sun, Yujie Jin, Chuhao Lin, Jiyong Liu, Simon Duttwyler
{"title":"Synthesis of {CB11} Monocarborane Sulfonamides by B2-Selective Rhodium-Catalyzed B−H Activation","authors":"Zehua Ye,&nbsp;Jizeng Sun,&nbsp;Yujie Jin,&nbsp;Chuhao Lin,&nbsp;Jiyong Liu,&nbsp;Simon Duttwyler","doi":"10.1002/hlca.202300144","DOIUrl":"10.1002/hlca.202300144","url":null,"abstract":"<p>The synthesis of monocarborane sulfonamides is reported. The methodology relies on coupling of the anionic {CB<sub>11</sub>} boron cluster to sulfonyl azides. Under rhodium catalysis and with the assistance of a pyridine or pyrimidine directing group at the C1 position, the cluster undergoes B−H activation. Conditions have been identified that lead to B2-selective mono-sulfonamidation with concomitant loss of N<sub>2</sub>. The protocol requires no additional ligand, oxidant or base and enables B−N bond formation with various monocarborane and sulfonyl azide inputs. The new products possess the structure [1-(heteroaryl)-2-(NHSO<sub>2</sub>Ar)−CB<sub>11</sub>H<sub>10</sub>]<sup>−</sup> and have been fully characterized by NMR spectroscopy and mass spectrometry. In addition, three solid state structures confirm the particular B2 substitution pattern. Furthermore, the stoichiometric reaction of the pyridinyl monocarborane precursor with Rh(III) affords a cyclometalated complex with a direct B−Rh bond that has also been characterized by X-ray crystallography.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2023-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135385399","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
Construction of Cyclobutane-Centered Tricyclic Caged Skeleton through a [5,5]-Rearrangement Triggered Cascade 通过[5,5]-重排触发级联构建以环丁烷为中心的三环笼状骨架
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2023-09-28 DOI: 10.1002/hlca.202300149
Mengjie Hu, Mengjiao Zhu, Liying Ru, Jiangtao Ji, Ming Bao, Bo Peng
{"title":"Construction of Cyclobutane-Centered Tricyclic Caged Skeleton through a [5,5]-Rearrangement Triggered Cascade","authors":"Mengjie Hu,&nbsp;Mengjiao Zhu,&nbsp;Liying Ru,&nbsp;Jiangtao Ji,&nbsp;Ming Bao,&nbsp;Bo Peng","doi":"10.1002/hlca.202300149","DOIUrl":"10.1002/hlca.202300149","url":null,"abstract":"<p>In this report, we describe the combination of [5,5]-rearrangement-triggered dearomatization recently developed in our laboratory with an intramolecular formal [2+2]-cycloaddition for constructing an intriguing polysubstituted tricyclo[4.2.1.0<sup>3,8</sup>]nonane derivatives. The synthesis features the use of simple and readily available three distinct starting materials including aryl sulfoxides, allyl nitriles, and certain nucleophiles or dienes which directly enriches the diversity of target molecules. This study provides an entirely new protocol for the synthesis of cyclobutane-centered tricyclic caged skeleton.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2023-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135385661","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
The Honeysuckle and the Bindweed Revisited: Synthesis and Stereochemistry of Extended Helical Structures from Coordination Complexes 金银花和联花:配位配合物扩展螺旋结构的合成和立体化学
IF 1.8 4区 化学
Helvetica Chimica Acta Pub Date : 2023-09-28 DOI: 10.1002/hlca.202300120
Alan M. Downward, Matteo Granelli, Celine Besnard, Laure Guénée, Alan F. Williams
{"title":"The Honeysuckle and the Bindweed Revisited: Synthesis and Stereochemistry of Extended Helical Structures from Coordination Complexes","authors":"Alan M. Downward,&nbsp;Matteo Granelli,&nbsp;Celine Besnard,&nbsp;Laure Guénée,&nbsp;Alan F. Williams","doi":"10.1002/hlca.202300120","DOIUrl":"10.1002/hlca.202300120","url":null,"abstract":"<p>We report structural studies of a chiral tridentate ligand which forms helical cubanes with cobalt(II) and manganese(II). A quadruple helicate with (<i>P</i>)<i>-</i>chirality is obtained using a (<i>S</i>)-ligand with cobalt(II) but the ligand binds manganese(II) in one of two possible orientations and either (<i>P</i>)<i>-</i> or (<i>M</i>)-quadruple helicates may be observed for a given ligand enantiomer. The helicates may be linked into extended structures by <i>p</i>-nitrobenzoate capping ligands which show stacking interactions with neighbouring complexes. With cobalt(II) we find an extended helical structure with (<i>M</i>)-chirality linking helicates which themselves have (<i>P</i>)<i>-</i>chirality. With manganese(II) we observe a remarkable structure with extended (<i>M</i>)-helices coexisting with extended (<i>P</i>)<i>-</i>helices.</p>","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2023-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202300120","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135386434","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
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