Helvetica Chimica Acta最新文献_第9页

A Practical and Scalable Non-Photonic Decarboxylative C−N Coupling of Bicyclo[1.1.1]Pentane Carboxylate by Leveraging High Throughput Experimentation 利用高通量实验实现双环[1.1.1]戊烷羧酸盐的实用、可扩展的非光子脱羧 C-N 偶联反应

IF 1.8 4区化学

Helvetica Chimica Acta Pub Date : 2023-11-04 DOI: 10.1002/hlca.202300158

Nathan J. Gesmundo, Lei Shi, Russell C. Smith

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Scalable Preparation of 1-Aminoethyl Substituted Chromanes 1-Aminoethyl Substituted Chromanes 的规模化制备

IF 1.8 4区化学

Helvetica Chimica Acta Pub Date : 2023-11-03 DOI: 10.1002/hlca.202300187

Stefan Diethelm, Gunther Schmidt, Thierry Sifferlen, Amandine Boller, Laurent Cornu, Christine Schmitt

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Prediction of Reaction Performance by Machine Learning Using Streamlined Features: NMR Chemical Shifts as Familiar Descriptors 通过机器学习使用精简特征预测反应性能：将核磁共振化学位移作为熟悉的描述符

IF 1.8 4区化学

Helvetica Chimica Acta Pub Date : 2023-10-27 DOI: 10.1002/hlca.202300165

Su-min Song, Ha Eun Kim, Hyun Woo Kim, Won-jin Chung

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Marina Uzelac 玛丽娜-乌泽拉茨

IF 1.8 4区化学

Helvetica Chimica Acta Pub Date : 2023-10-24 DOI: 10.1002/hlca.202300183

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A Multiplex GPCR-Mediated Peptide Tagging System for a Growing Yeast Synthetic Biology Toolbox 用于不断扩大的酵母合成生物学工具箱的多重 GPCR 介导多肽标记系统

IF 1.8 4区化学

Helvetica Chimica Acta Pub Date : 2023-10-22 DOI: 10.1002/hlca.202300094

Joseph Matragrano, Virginia W. Cornish, Sonja Billerbeck

{"title":"A Multiplex GPCR-Mediated Peptide Tagging System for a Growing Yeast Synthetic Biology Toolbox","authors":"Joseph Matragrano, Virginia W. Cornish, Sonja Billerbeck","doi":"10.1002/hlca.202300094","DOIUrl":"10.1002/hlca.202300094","url":null,"abstract":"Straightforward methods for specifically detecting and quantifying proteins are essential for both basic and applied research and notably in synthetic biology. Previously we demonstrated that the yeast mating pathway could be hijacked to detect species-specific fungal peptide pheromones using their corresponding mating GPCRs. Here we asked if our yeast biosensor could detect proteins in addition to peptides – a question not previously resolved in the literature. As such, we repurposed the Saccharomyces cerevisiae fungal mating pheromone α-factor as a peptide tag and fused it terminally and internally to the protein Smt3. Our biosensor was able to detect the tagged protein in the nanomolar range using fluorescence as a read-out. We extended the assay to four additional orthogonal peptide pheromone tags, demonstrating a cheap, non-labor-intensive, and high-throughput assay compatible with multiplexing for protein detection. With its ability to detect proteins our living yeast biosensor could be useful for the optimization of protein producing cell-factories, for building logic gates and myriad other applications in synthetic biology.","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2023-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/hlca.202300094","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135461371","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

Dynemicin A Derivatives as Potential Cancer Chemotherapeutics by Mutasynthesis 通过突变合成将生物碱 A 衍生物用作潜在的癌症化疗药物

IF 1.8 4区化学

Helvetica Chimica Acta Pub Date : 2023-10-21 DOI: 10.1002/hlca.202300123

Paramita Pal, Jamie R. Alley, Douglas R. Cohen, Craig A. Townsend

{"title":"Dynemicin A Derivatives as Potential Cancer Chemotherapeutics by Mutasynthesis","authors":"Paramita Pal, Jamie R. Alley, Douglas R. Cohen, Craig A. Townsend","doi":"10.1002/hlca.202300123","DOIUrl":"10.1002/hlca.202300123","url":null,"abstract":"The enediyne antitumor antibiotics have remarkable structures and exhibit potent DNA cleavage properties that have inspired continued interest as cancer therapeutics. Their complex structures and high reactivity, however, pose formidable challenges to their production and development in the clinic. We report here proof-of-concept studies using a mutasynthesis strategy to combine chemical synthesis of select modifications to a key iodoanthracene-γ-thiolactone intermediate in the biosynthesis of dynemicin A and all other known anthraquinone-fused enediynes (AFEs). By chemical complementation of a mutant bacterial producer that is incapable of synthesizing this essential building block, we show that derivatives of dynemicin can be prepared substituted in the A-ring of the anthraquinone motif. In the absence of competition from native production of this intermediate, the most efficient utilization of these externally-supplied structural analogues for precursor-directed biosynthesis becomes possible. To achieve this goal, we describe the required Δorf15 blocked mutant and a general synthetic route to a library of iodoanthracene structural variants. Their successful incorporation opens the door to enhancing DNA binding and tuning the bioreductive activation of the modified enediynes for DNA cleavage.","PeriodicalId":12842,"journal":{"name":"Helvetica Chimica Acta","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2023-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135512306","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

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

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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

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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

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, Tony Fleischer","doi":"10.1002/hlca.202300167","DOIUrl":"10.1002/hlca.202300167","url":null,"abstract":"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 para-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 para-selective formylation, followed by transformation of the intermediate aldehyde into the nitrile with hydroxylamine-O-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.","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