Chirality最新文献_第3页

Recent Advances in Enantioselective Desymmetrization Enabled by Chiral Phosphoric Acid Catalysis 手性磷酸催化对映选择性去对称研究进展。

IF 2.4 4区化学

Chirality Pub Date : 2026-08-25 DOI: 10.1002/chir.70141

Dekun Zhang, Bubin Xu, Yuxiu Yang, Ding Zhang

引用次数: 0

Prebiotic Absolute Asymmetric Synthesis of d-Ribose on Wollastonite 硅灰石上d-核糖的绝对不对称合成

IF 2.4 4区化学

Chirality Pub Date : 2026-08-20 DOI: 10.1002/chir.70139

Wendi Zhang, Yang Gao, Jiao Wang, Quanzheng Deng, Lu Han, Wanning Zhang, Yuxi Fang

{"title":"Prebiotic Absolute Asymmetric Synthesis of d-Ribose on Wollastonite","authors":"Wendi Zhang, Yang Gao, Jiao Wang, Quanzheng Deng, Lu Han, Wanning Zhang, Yuxi Fang","doi":"10.1002/chir.70139","DOIUrl":"https://doi.org/10.1002/chir.70139","url":null,"abstract":"<div>\u0000 \u0000 ATP is the core substance of energy metabolism in all forms of life. The chirality of d-ribose is essential for ATP's function, ensuring efficient molecular recognition, metabolic stability, and co-evolution with RNA in biological processes. However, origin of chirality of d-ribose is still unknown. Here, we demonstrate that wollastonite, an abundant Earth mineral, catalyzes the formose reaction between formaldehyde and glycolaldehyde and achieves high enantioselectivity (63.3%–91.3% ee) toward d-ribose. The lower energy barrier for the transition state of d-glyceraldehyde compared to that of l-glyceraldehyde, which possesses a similar configuration to glyceraldehyde, results in the enantioselective synthesis of ribose. Experimental and computational studies reveal that the surface chirality of wollastonite, which is characterized by its wavy atomic arrangement, selectively reduces the adsorption energy of the d-glyceraldehyde intermediate compared to its l-enantiomer. This preferential adsorption kinetically promotes the d-glyceraldehyde pathway and steers the reaction toward d-ribose. Our work establishes wollastonite as an intrinsically enantioselective mineral catalyst, provides a mechanistic foundation for prebiotic chiral selection toward d-ribose, and highlights surface design principles for asymmetric synthesis.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"38 9","pages":""},"PeriodicalIF":2.4,"publicationDate":"2026-08-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148784647","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

Evaluating the Solvent and pH Effect in the Inversion of the Circular Dichroism Signal of S-Naproxen s -萘普生圆二色信号反演中溶剂和pH效应的评价

IF 2.4 4区化学

Chirality Pub Date : 2026-08-19 DOI: 10.1002/chir.70137

Lucas Chuman Santana, Eduardo de Faria Franca, Valdecir Farias Ximenes, Aguinaldo Robinson de Souza, Nelson Henrique Morgon

{"title":"Evaluating the Solvent and pH Effect in the Inversion of the Circular Dichroism Signal of S-Naproxen","authors":"Lucas Chuman Santana, Eduardo de Faria Franca, Valdecir Farias Ximenes, Aguinaldo Robinson de Souza, Nelson Henrique Morgon","doi":"10.1002/chir.70137","DOIUrl":"https://doi.org/10.1002/chir.70137","url":null,"abstract":"S-Naproxen (NPX) exhibits an unusual inversion of its ECD spectrum upon solvent change, a phenomenon that this work analyzes both experimentally and theoretically. By evaluating NPX in water, ethanol, and acetonitrile, it was observed that pH variation shifts the chemical equilibrium between protonated and deprotonated forms, making this transition the direct cause of the ECD signal inversion. Molecular dynamics and TD-DFT (CAM-B3LYP/aug-cc-pVDZ) calculations corroborated the experimental data, demonstrating that structural changes alter the predominant electronic transitions from π → π* in NPX to n → π* in the NPX− anion, as evidenced by transition density differences and natural transition orbitals (NTOs). These findings demonstrate that explicit solvent treatment and statistical analysis are requisite to accurately reproduce the data, validating that the negative signal in water and the positive signal in acetonitrile is governed by the predominant species dictated by the chemical equilibrium.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"38 9","pages":""},"PeriodicalIF":2.4,"publicationDate":"2026-08-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.70137","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148784749","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

Rapid Quantitative Determination of Enantiomeric Excess by Vibrational Circular Dichroism Using Noise Based Spectral Selection 基于噪声的光谱选择振动圆二色快速定量测定对映体过量

IF 2.4 4区化学

Chirality Pub Date : 2026-08-18 DOI: 10.1002/chir.70134

Amy M. Jackson, John R. Bows, Geoff R. Nash

引用次数: 0

Stereodivergent Synthesis of C5-α-Substituted Linezolid Derivatives From D-Mannitol and Structure–Antibacterial Activity Evaluation d -甘露醇C5-α-取代利奈唑胺衍生物的立体发散合成及结构-抗菌活性评价。

IF 2.4 4区化学

Chirality Pub Date : 2026-08-16 DOI: 10.1002/chir.70138

José A. Gálvez, Laura Sanz-Asensio, Ramón Badorrey, Jesús Gonzalo-Asensio

{"title":"Stereodivergent Synthesis of C5-α-Substituted Linezolid Derivatives From D-Mannitol and Structure–Antibacterial Activity Evaluation","authors":"José A. Gálvez, Laura Sanz-Asensio, Ramón Badorrey, Jesús Gonzalo-Asensio","doi":"10.1002/chir.70138","DOIUrl":"10.1002/chir.70138","url":null,"abstract":"A stereodivergent synthetic strategy enabling access to enantiopure C5-α-substituted linezolid analogues has been developed from D-mannitol as an inexpensive chiral pool precursor. The approach provides controlled access to both syn- and anti-configured derivatives bearing ethyl or phenyl substituents at the α-position of the C5 acetamidomethyl side chain, thereby introducing a second stereogenic center with high diastereocontrol. Key steps include highly selective nucleophilic additions of organometallic reagents to chiral N-benzyl imines derived from protected D-glyceraldehyde and base-promoted condensation of enantiopure N-Boc-aminoepoxides with aryl carbamates to construct the 2-oxazolidinone core. Comparative analysis of both configurational series revealed marked differences in cyclization efficiency, particularly for α-phenyl-substituted intermediates in the anti series, highlighting the steric sensitivity of oxazolidinone formation. In vitro assays against Gram-positive and Mycobacterium spp. species showed complete loss of antibacterial activity for all α-substituted derivatives, irrespective of configuration. These results establish a clear structural limitation at C5 and demonstrate that steric expansion at the α-position overrides stereochemical effects. This study underscores the value of stereodivergent synthesis for rigorously disentangling configurational and substituent contributions in chiral bioactive scaffolds.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"38 9","pages":""},"PeriodicalIF":2.4,"publicationDate":"2026-08-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.70138","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148757684","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

Methamphetamine Enantiomers: From Chemical Synthesis to Biological Fate 甲基苯丙胺对映体：从化学合成到生物命运

IF 2.4 4区化学

Chirality Pub Date : 2026-08-13 DOI: 10.1002/chir.70136

Larissa Pires do Espírito Santo, Renato Lúcio de Carvalho, Juliana Almeida Sad, Pedro Henrique Costa dos Santos, Rhaiza Silva Domingues, Gabriele de Azevedo Cardoso, Karine Braga Enes, Gisele Assis Castro Goulart, Maila de Castro Lourenço das Neves, Ângelo de Fátima

{"title":"Methamphetamine Enantiomers: From Chemical Synthesis to Biological Fate","authors":"Larissa Pires do Espírito Santo, Renato Lúcio de Carvalho, Juliana Almeida Sad, Pedro Henrique Costa dos Santos, Rhaiza Silva Domingues, Gabriele de Azevedo Cardoso, Karine Braga Enes, Gisele Assis Castro Goulart, Maila de Castro Lourenço das Neves, Ângelo de Fátima","doi":"10.1002/chir.70136","DOIUrl":"https://doi.org/10.1002/chir.70136","url":null,"abstract":"Methamphetamine, an amphetamine-type stimulant, is a potent and psychoactive compound distinguished by the presence of a single stereogenic center in its structure. Consequently, it exists as two enantiomers: (S)-(+)-methamphetamine [(S)-(+)-MA (1)] and (R)-(−)-methamphetamine [(R)-(−)-MA (2)]. The chirality of these molecules confers distinct biological and pharmacological properties, with notable differences between the two forms. These enantioselective variations extend beyond their mechanisms of action, encompassing differences in the central nervous system interactions, metabolism, excretion, and other physiological processes. Understanding these disparities is crucial for elucidating the pharmacological and potential therapeutic profiles of each enantiomer. Achieving such insight requires examination of the enantioselective synthetic routes through which the desired chirality can be either inherited or constructed. This review integrates chemical and biological perspectives to provide a comprehensive overview of both methamphetamine enantiomers, thereby bridging the gap between laboratory synthesis and biological behavior in these two chemically fascinating yet dangerous molecules.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"38 9","pages":""},"PeriodicalIF":2.4,"publicationDate":"2026-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.70136","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148719259","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

Application of Analytical Techniques to Chiral Amino Acid Profiling in Clinical Samples: Bridging Chemistry and Disease Research 分析技术在临床样品手性氨基酸谱分析中的应用：连接化学与疾病研究。

IF 2.4 4区化学

Chirality Pub Date : 2026-08-10 DOI: 10.1002/chir.70132

Ashwini Chawathe, Sanju, Pradnya Sahane, Nitish Sharma

{"title":"Application of Analytical Techniques to Chiral Amino Acid Profiling in Clinical Samples: Bridging Chemistry and Disease Research","authors":"Ashwini Chawathe,  Sanju, Pradnya Sahane, Nitish Sharma","doi":"10.1002/chir.70132","DOIUrl":"10.1002/chir.70132","url":null,"abstract":"<div>\u0000 \u0000 Amino acids are the basic building blocks of proteins that are required to control various vital biological processes, including immune response, hormone regulation, metabolic control, and gene expression. Although L-amino acids are the primary components of protein synthesis, their mirror-image counterparts, D-amino acids, exhibit distinct pharmacological and biological characteristics. As a result, reliable identification and measurement of these enantiomers have become critical criteria in biology, chemistry, and medicine. Because changes in D-amino acid levels are closely related to the onset and progression of a variety of human disorders, the therapeutic utility of these amino acids as diagnostic biomarkers is gaining traction. This article investigates the vital role of chiral amino acids in clinical disorders, with a particular emphasis on their implications for neurological conditions. It also evaluates the several techniques and analytical systems used to identify enantiomeric amino acids in complex biological matrices, focusing on current technological breakthroughs that have increased the sensitivity and precision of these evaluations.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"38 8","pages":""},"PeriodicalIF":2.4,"publicationDate":"2026-08-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148705412","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

Chiral Tetraazacalix-Triazine Derivatives as Organocatalysts for Asymmetric Direct Aldol Reactions: Synthesis and Enantioselective Evaluation 手性四氮杂环-三嗪衍生物作为不对称直接醛醇反应的有机催化剂：合成和对映选择性评价。

IF 2.4 4区化学

Chirality Pub Date : 2026-08-04 DOI: 10.1002/chir.70130

Ummu Ozgun, Hayriye Nevin Genc, Abdulkadir Sirit

引用次数: 0

Absolute Configuration Assignment From a Single Reflection Using Resonant X-Ray Diffraction 用共振x射线衍射从单反射得到绝对构型分配。

IF 2.4 4区化学

Chirality Pub Date : 2026-08-04 DOI: 10.1002/chir.70129

Anmol Andotra, Fabian Gasser, Ferdinando Malagreca, Roland C. Fischer, Yves H. Geerts, Roland Resel

{"title":"Absolute Configuration Assignment From a Single Reflection Using Resonant X-Ray Diffraction","authors":"Anmol Andotra, Fabian Gasser, Ferdinando Malagreca, Roland C. Fischer, Yves H. Geerts, Roland Resel","doi":"10.1002/chir.70129","DOIUrl":"10.1002/chir.70129","url":null,"abstract":"Determination of the absolute configuration of chiral molecules is essential across multiple scientific disciplines, as handedness determines the chiroptical, biological, and pharmaceutical properties. For crystalline materials, single crystal x-ray diffraction is the standard technique for assigning the absolute configuration. However, its application typically requires a large number of reflections and analysis of Friedel pair intensities using the Flack parameter or related approaches, such as those of Hooft or Parsons. Here, we introduce a conceptually distinct approach for determining the absolute configuration of a known crystal structure, based on the x-ray energy dependent intensity of a single Bragg reflection that is sensitive to the absolute configuration. By monitoring the variation in the intensity of a Bragg peak across an absorption edge, this method provides an unambiguous probe of chirality. The proposed approach is demonstrated for the <math>\u0000 <semantics>\u0000 <mrow>\u0000 <mn>211</mn>\u0000 </mrow>\u0000 <annotation>$$ 211 $$</annotation>\u0000 </semantics></math> reflection of a 2-(3-bromophenyl)-N,N-diisopropyl-2-oxoacetamide single crystal, showing that the absolute configuration can be reliably determined from a single reflection. To confirm the assignment of chirality and assess potential limitations, the x-ray energy dependence of additional diffraction peaks was also investigated. This method is particularly advantageous for systems with a limited number of accessible reflections, where conventional statistical methods based on Flack parameter analysis are not reliable.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"38 8","pages":""},"PeriodicalIF":2.4,"publicationDate":"2026-08-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13434679/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148668637","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

Mass Spectrometry in Chiral Analysis and Synthesis 质谱法在手性分析与合成

IF 2.4 4区化学

Chirality Pub Date : 2026-07-31 DOI: 10.1002/chir.70126

Brison A. Shira, Mahdiyeh Shahi, R. Graham Cooks

{"title":"Mass Spectrometry in Chiral Analysis and Synthesis","authors":"Brison A. Shira, Mahdiyeh Shahi, R. Graham Cooks","doi":"10.1002/chir.70126","DOIUrl":"https://doi.org/10.1002/chir.70126","url":null,"abstract":"Mass spectrometry (MS) has a role to play in chiral chemistry, in part through methods based on microdroplets and non-covalent molecular clusters. High-throughput MS reaction screening and chiral anal0ysis use microdroplet sprays to perform accelerated nanoscale chemistry, including the synthesis of heterocyclics and other drug candidates using new high-throughput automated instrumentation. The kinetic method of chiral analysis measures competitive dissociation reactions of molecular clusters (usually trinary coordination complexes) to determine enantiomeric excess (e.e.). A very different molecular cluster, the serine octamer, an active research topic for two decades, may hold implications in the search for the origins of homochirality. Lastly, the recently reported direct discrimination of enantiomers using an ion trap mass spectrometer (ITMS) is revisited. These four examples, combined with recent findings concerning chiral post-translational modifications in cancer biology, represent exciting research developments that deploy the advantages of MS (throughput, molecular specificity, and sample size) to improve chiral synthesis and analysis.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"38 8","pages":""},"PeriodicalIF":2.4,"publicationDate":"2026-07-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.70126","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148617376","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