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Synthesis of HBC fluorophores with an electrophilic handle for covalent attachment to Pepper RNA. 与辣椒RNA共价连接的亲电柄HBC荧光团的合成。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-04-04 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.56
Raphael Bereiter, Ronald Micura
{"title":"Synthesis of HBC fluorophores with an electrophilic handle for covalent attachment to Pepper RNA.","authors":"Raphael Bereiter, Ronald Micura","doi":"10.3762/bjoc.21.56","DOIUrl":"https://doi.org/10.3762/bjoc.21.56","url":null,"abstract":"<p><p>The fluorescent light-up aptamer (FLAP) Pepper can utilize fluorophores that are equipped with an electrophilic handle for the covalent attachment of the surrogate to the RNA. The resulting irreversibly tethered dye-RNA complexes have opened up new avenues for RNA imaging in live cells. Here, we report the syntheses of such modified HBC530 ((4-((2-hydroxyethyl)(methyl)amino)benzylidene)cyanophenylacetonitrile) fluorophores for easy access, which will contribute to the rapid dissemination of the RNA imaging approaches associated therewith.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"727-735"},"PeriodicalIF":2.2,"publicationDate":"2025-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11995720/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143968580","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
Acyclic cucurbit[n]uril bearing alkyl sulfate ionic groups. 含烷基硫酸盐离子基的无环葫芦[n]。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-04-03 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.55
Christian Akakpo, Peter Y Zavalij, Lyle Isaacs
{"title":"Acyclic cucurbit[<i>n</i>]uril bearing alkyl sulfate ionic groups.","authors":"Christian Akakpo, Peter Y Zavalij, Lyle Isaacs","doi":"10.3762/bjoc.21.55","DOIUrl":"10.3762/bjoc.21.55","url":null,"abstract":"<p><p>We report the synthesis and characterization of a new acyclic cucurbit[<i>n</i>]uril (CB[<i>n</i>]) host <b>C1</b> that features four alkyl sulfate ionic groups. The X-ray crystal structure of the <b>C1·Me</b> <b><sub>6</sub></b> <b>CHDA</b> complex is reported. Host <b>C1</b> is significantly less soluble in water (4 mM) compared to the analogous acyclic CB[<i>n</i>] host <b>M1</b> which features sulfonate ionic groups (346 mM). Host <b>C1</b> does not undergo significant self-association according to the results of <sup>1</sup>H NMR dilution experiments. The molecular recognition behavior of the hosts <b>C1</b> and <b>M1</b> toward a panel of seven ammonium ions was explored by <sup>1</sup>H NMR spectroscopy and isothermal titration calorimetry (ITC). We find that <b>C1</b> generally binds slightly more tightly than <b>M1</b> toward a specific guest. <b>C1</b> binds more tightly to quaternary ammonium guests compared to the corresponding primary ammonium ions.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"717-726"},"PeriodicalIF":2.2,"publicationDate":"2025-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11973588/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143802233","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
Origami with small molecules: exploiting the C-F bond as a conformational tool. 小分子折纸：利用C-F键作为构象工具。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-04-02 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.54
Patrick Ryan, Ramsha Iftikhar, Luke Hunter
{"title":"Origami with small molecules: exploiting the C-F bond as a conformational tool.","authors":"Patrick Ryan, Ramsha Iftikhar, Luke Hunter","doi":"10.3762/bjoc.21.54","DOIUrl":"10.3762/bjoc.21.54","url":null,"abstract":"<p><p>When present within an organic molecule, the C-F bond tends to align in predictable ways with neighbouring functional groups, due to stereoelectronic effects such as hyperconjugation and electrostatic attraction/repulsion. These fluorine-derived conformational effects have been exploited to control the shapes, and thereby enhance the properties, of a wide variety of functional molecules including pharmaceutical agents, liquid crystals, fragrance chemicals, organocatalysts, and peptides. This comprehensive review summarises developments in this field during the period 2010-2024.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"680-716"},"PeriodicalIF":2.2,"publicationDate":"2025-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11973591/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143802234","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
Photochemically assisted synthesis of phenacenes fluorinated at the terminal benzene rings and their electronic spectra. 苯环末端氟化苯的光化学辅助合成及其电子谱。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-03-24 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.53
Yuuki Ishii, Minoru Yamaji, Fumito Tani, Kenta Goto, Yoshihiro Kubozono, Hideki Okamoto
{"title":"Photochemically assisted synthesis of phenacenes fluorinated at the terminal benzene rings and their electronic spectra.","authors":"Yuuki Ishii, Minoru Yamaji, Fumito Tani, Kenta Goto, Yoshihiro Kubozono, Hideki Okamoto","doi":"10.3762/bjoc.21.53","DOIUrl":"10.3762/bjoc.21.53","url":null,"abstract":"<p><p>[<i>n</i>]Phenacenes ([<i>n</i>] = 5-7), octafluorinated at the terminal benzene rings (F<sub>8</sub>-phenacenes: <b>F</b> <b><sub>8</sub></b> <b>PIC</b>, <b>F</b> <b><sub>8</sub></b> <b>FUL</b>, and <b>F</b> <b><sub>8</sub></b> <b>7PHEN</b>), were photochemically synthesized, and their electronic spectra were investigated to reveal the effects of the fluorination on the electronic features of phenacene molecules. F<sub>8</sub>-Phenacenes were conveniently synthesized by the Mallory photoreaction of the corresponding fluorinated diarylethenes as the key step. Upon fluorination on the phenacene cores, the absorption and fluorescence bands of the F<sub>8</sub>-phenacenes in CHCl<sub>3</sub> systematically red-shifted by ca. 3-5 nm compared to those of the corresponding parent phenacenes. The vibrational progressions of the absorption and fluorescence bands were little affected by the fluorination in the solution phase. In the solid state, the absorption band of F<sub>8</sub>-phenacenes appeared in the similar wavelength region for the corresponding parent phenacenes whereas their fluorescence bands markedly red-shifted and broadened. These observations suggest that the intermolecular interactions of excited-state F<sub>8</sub>-phenacene molecules are significantly different from those of the corresponding parent molecules, most likely due to different crystalline packing motifs.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"670-679"},"PeriodicalIF":2.2,"publicationDate":"2025-03-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11956079/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143750927","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
Asymmetric synthesis of fluorinated derivatives of aromatic and γ-branched amino acids via a chiral Ni(II) complex. 手性Ni（II）配合物不对称合成芳香和γ支链氨基酸的氟化衍生物。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-03-21 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.52
Maurizio Iannuzzi, Thomas Hohmann, Michael Dyrks, Kilian Haoues, Katarzyna Salamon-Krokosz, Beate Koksch
{"title":"Asymmetric synthesis of fluorinated derivatives of aromatic and γ-branched amino acids via a chiral Ni(II) complex.","authors":"Maurizio Iannuzzi, Thomas Hohmann, Michael Dyrks, Kilian Haoues, Katarzyna Salamon-Krokosz, Beate Koksch","doi":"10.3762/bjoc.21.52","DOIUrl":"10.3762/bjoc.21.52","url":null,"abstract":"<p><p>Fluorinated amino acids are essential building blocks in the spheres of protein engineering and medicinal chemistry. In the last decades, a large number of different synthetic strategies have been developed to produce a large variety of fluorinated amino acids. Still, obtaining fluorinated amino acids in great quantities can be challenging, or the corresponding pathways are heavily time-consuming and synthetically challenging. In this context, chiral Ni(II) complexes can be powerful tools to obtain tailor‑made non‑canonical amino acids. In this work, we wanted to take advantage of this strategy and extend the range of this method to include additional fluorinated amino acids. We synthesized two fluorinated analogs of phenylalanine, which are still unexplored in the context of peptide and protein chemistry. Furthermore, both diastereomers of trifluoroleucine were synthesized, demonstrating that the described strategy can also be applied to synthesize enantio‑ and diastereomerically pure γ‑branched fluorinated amino acids. This work further underlines the importance of chiral Ni(II) complexes in the synthesis of fluorinated amino acids.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"659-669"},"PeriodicalIF":2.2,"publicationDate":"2025-03-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11931639/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143699600","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
Recent advances in allylation of chiral secondary alkylcopper species. 手性仲烷基铜烯丙基化研究进展。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-03-20 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.51
Minjae Kim, Gwanggyun Kim, Doyoon Kim, Jun Hee Lee, Seung Hwan Cho
{"title":"Recent advances in allylation of chiral secondary alkylcopper species.","authors":"Minjae Kim, Gwanggyun Kim, Doyoon Kim, Jun Hee Lee, Seung Hwan Cho","doi":"10.3762/bjoc.21.51","DOIUrl":"10.3762/bjoc.21.51","url":null,"abstract":"<p><p>The transition-metal-catalyzed asymmetric allylic substitution represents a pivotal methodology in organic synthesis, providing remarkable versatility for complex molecule construction. Particularly, the generation and utilization of chiral secondary alkylcopper species have received considerable attention due to their unique properties in stereoselective allylic substitution. This review highlights recent advances in copper-catalyzed asymmetric allylic substitution reactions with chiral secondary alkylcopper species, encompassing several key strategies for their generation: stereospecific transmetalation of organolithium and organoboron compounds, copper hydride catalysis, and enantiotopic-group-selective transformations of 1,1-diborylalkanes. Detailed mechanistic insights into stereochemical control and current challenges in this field are also discussed.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"639-658"},"PeriodicalIF":2.2,"publicationDate":"2025-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11931642/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143699609","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
Entry to 2-aminoprolines via electrochemical decarboxylative amidation of N‑acetylamino malonic acid monoesters. 通过N -乙酰氨基丙二酸单酯的电化学脱羧酰胺化进入2-氨基脯氨酸。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-03-19 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.50
Olesja Koleda, Janis Sadauskis, Darja Antonenko, Edvards Janis Treijs, Raivis Davis Steberis, Edgars Suna
{"title":"Entry to 2-aminoprolines via electrochemical decarboxylative amidation of <i>N</i>‑acetylamino malonic acid monoesters.","authors":"Olesja Koleda, Janis Sadauskis, Darja Antonenko, Edvards Janis Treijs, Raivis Davis Steberis, Edgars Suna","doi":"10.3762/bjoc.21.50","DOIUrl":"10.3762/bjoc.21.50","url":null,"abstract":"<p><p>The electrochemical synthesis of 2-aminoprolines based on anodic decarboxylation-intramolecular amidation of readily available <i>N</i>-acetylamino malonic acid monoesters is reported. The decarboxylative amidation under Hofer-Moest reaction conditions proceeds in an undivided cell under constant current conditions in aqueous acetonitrile and provides access to <i>N</i>-sulfonyl, <i>N</i>-benzoyl, and <i>N</i>-Boc-protected 2-aminoproline derivatives.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"630-638"},"PeriodicalIF":2.2,"publicationDate":"2025-03-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11931647/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143699602","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
Photocatalyzed elaboration of antibody-based bioconjugates. 光催化制备基于抗体的生物偶联物。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-03-18 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.49
Marine Le Stum, Eugénie Romero, Gary A Molander
{"title":"Photocatalyzed elaboration of antibody-based bioconjugates.","authors":"Marine Le Stum, Eugénie Romero, Gary A Molander","doi":"10.3762/bjoc.21.49","DOIUrl":"10.3762/bjoc.21.49","url":null,"abstract":"<p><p>Antibody-drug conjugates (ADCs) represent a promising class of targeted therapeutics, combining the specificity of antibodies with the potency of cytotoxic drugs to enhance therapeutic efficacy while minimizing off-target effects. The development of new chemical methods for bioconjugation is essential to generate ADCs and to optimize their stability, efficacy, and safety. Traditional conjugation methods often face challenges related to site-selectivity and heterogeneous product mixtures, highlighting the need to develop new, innovative chemical strategies. Photoredox chemistry emerges as a powerful tool in this context, enabling precise, mild, and selective modifications of peptides and proteins. By harnessing light to drive chemical transformations, photoredox techniques can facilitate the synthesis of antibody bioconjugates. This perspective will discuss the drive to develop and empower photoredox methods applied to antibody functionalization.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"616-629"},"PeriodicalIF":2.2,"publicationDate":"2025-03-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11931643/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143699605","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
Semisynthetic derivatives of massarilactone D with cytotoxic and nematicidal activities. 具有细胞毒和杀线虫活性的马尾松内酯D的半合成衍生物。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-03-17 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.48
Rémy B Teponno, Sara R Noumeur, Marc Stadler
{"title":"Semisynthetic derivatives of massarilactone D with cytotoxic and nematicidal activities.","authors":"Rémy B Teponno, Sara R Noumeur, Marc Stadler","doi":"10.3762/bjoc.21.48","DOIUrl":"10.3762/bjoc.21.48","url":null,"abstract":"<p><p>Massarilactones constitute a rare class of polyketides produced mainly by endophytic fungi. Given that semisynthetic derivatives often exhibit biological activities greater than those of the substrates, seven previously unreported derivatives of massarilactone D, compounds <b>2</b>-<b>8</b>, were synthetized by acylation with methacryloyl chloride, cinnamoyl chloride, 4-bromobenzoyl chloride, <i>trans</i>-2-methyl-2-butenoyl chloride, and crotonyl chloride. These compounds were evaluated for their cytotoxic activity against the murine fibroblasts L929, human cervix carcinoma KB-3-1, human lung carcinoma A549, human prostate cancer PC-3, epidermoid carcinoma A431, ovarian carcinoma SKOV-3, and breast cancer MCF-7 cell lines. Compounds <b>2</b> and <b>3</b> exhibited significant cytotoxicity against all the tested cells. Some of the semisynthetic derivatives were also tested for their nematicidal activity and compound <b>4</b> displayed significant and selective nematicidal activity with LD<sub>90</sub> and LD<sub>50</sub> of 100 and 12.5 µg/mL, respectively. Since the parent compound was not active, the present study supports the fact that the acylation reaction can improve bioactivities of some natural products.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"607-615"},"PeriodicalIF":2.2,"publicationDate":"2025-03-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11931645/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143699611","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
Total synthesis of (±)-simonsol C using dearomatization as key reaction under acidic conditions. 在酸性条件下以脱芳为关键反应合成（±）-西蒙索尔C。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-03-17 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.47
Xiao-Yang Bi, Xiao-Shuai Yang, Shan-Shan Chen, Jia-Jun Sui, Zhao-Nan Cai, Yong-Ming Chuan, Hong-Bo Qin
{"title":"Total synthesis of (±)-simonsol C using dearomatization as key reaction under acidic conditions.","authors":"Xiao-Yang Bi, Xiao-Shuai Yang, Shan-Shan Chen, Jia-Jun Sui, Zhao-Nan Cai, Yong-Ming Chuan, Hong-Bo Qin","doi":"10.3762/bjoc.21.47","DOIUrl":"10.3762/bjoc.21.47","url":null,"abstract":"<p><p>The total synthesis of (±)-simonsol C was accomplished using a dearomatization under acidic conditions as key step to construct an aryl-containing quaternary center. The 6/5/6 benzofuran unit was formed through reductive elimination with Zn/AcOH and a spontaneous oxy-Michael addition. This synthesis consists of 8 steps and achieves an overall yield of 13%, making it the shortest known route.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"601-606"},"PeriodicalIF":2.2,"publicationDate":"2025-03-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11931641/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143699614","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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