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Chlorine Radical Mediated Deprotection of Aryl Ethers via Photocatalyzed Ligand-to-Metal Charge Transfer 氯自由基通过光催化配体-金属电荷转移介导芳基醚脱保护
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-06-16 DOI: 10.1002/ajoc.202500423
Honghao Chen, Yuhao Wang, Feixiang Yao, Dongya Fan, Prof. Dr. Jianbin Chen, Shouli Yu, Prof. Dr. Yan Tian, Prof. Dr. Yongli Du, Prof. Dr. Yuehui Li, Minghui Yu, Li Ma, Xiande Sun, Prof. Dr. Zunqi Liu, Prof. Dr. Aziz Bakhtiyarovich Ibragimov, Prof. Dr. Siyuan Liu
{"title":"Chlorine Radical Mediated Deprotection of Aryl Ethers via Photocatalyzed Ligand-to-Metal Charge Transfer","authors":"Honghao Chen,&nbsp;Yuhao Wang,&nbsp;Feixiang Yao,&nbsp;Dongya Fan,&nbsp;Prof. Dr. Jianbin Chen,&nbsp;Shouli Yu,&nbsp;Prof. Dr. Yan Tian,&nbsp;Prof. Dr. Yongli Du,&nbsp;Prof. Dr. Yuehui Li,&nbsp;Minghui Yu,&nbsp;Li Ma,&nbsp;Xiande Sun,&nbsp;Prof. Dr. Zunqi Liu,&nbsp;Prof. Dr. Aziz Bakhtiyarovich Ibragimov,&nbsp;Prof. Dr. Siyuan Liu","doi":"10.1002/ajoc.202500423","DOIUrl":"10.1002/ajoc.202500423","url":null,"abstract":"<p>A photochemical FeCl<sub>3</sub>-catalyzed the C(<i>sp<sup>3</sup></i>)-H activation of aryl ethers was achieved via hydrogen atom abstraction strategy of chlorine radicals. Followed by the tandem hydrolysis, the aryl ethers were converted into the corresponding phenol products (28 examples). Compared with traditional reductive deprotection methods for aryl ethers, such as Pd/C, Mg/alcohol system and so forth, our strategy features mild reaction conditions, atom economy, and wide functional group compatibility. In addition, several control experiments were conducted to investigate the reasonable mechanism.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 8","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144832679","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
Front Cover: Synthesis, Optical and Singlet Oxygen Generation Properties of Phenazinone-Based Photosensitizer with 5-Formyl-2-Thienyl Substituents (Asian J. Org. Chem. 6/2025) 封面：5-甲酰基-2-噻吩取代吩那嗪酮类光敏剂的合成、光学和单线态氧生成性能[j]。化学6/2025)
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-06-16 DOI: 10.1002/ajoc.202580601
Hiroto Tsuyama, Dr. Keiichi Imato, Prof. Dr. Yousuke Ooyama
{"title":"Front Cover: Synthesis, Optical and Singlet Oxygen Generation Properties of Phenazinone-Based Photosensitizer with 5-Formyl-2-Thienyl Substituents (Asian J. Org. Chem. 6/2025)","authors":"Hiroto Tsuyama,&nbsp;Dr. Keiichi Imato,&nbsp;Prof. Dr. Yousuke Ooyama","doi":"10.1002/ajoc.202580601","DOIUrl":"10.1002/ajoc.202580601","url":null,"abstract":"<p>In article number e202400781, Hiroto Tsuyama, Keiichi Imato, and Yousuke Ooyama accomplished the development of phenazinone-based photosensitizer with 5-formyl-2-thienyl substituents. It was fond that the introduction of 5-formyl-2-thienyl substituents into phenazinone chromophore leads to bathochromic shift of photoabsorption band. The photophysical and singlet oxygen (<sup>1</sup>O<sub>2</sub>) generation properties were revealed by the kinetic and thermodynamic analyses based on the experimental results and the theoretical calculations.\u0000\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure></p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 6","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202580601","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144292625","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
Switchable Reaction of p-Toluenesulfonyl Hydrazide With N-Heteroaryl Ketones: Base-Controlled Selective Synthesis of N-Heteroaryl Alcohols and [1, 2, 3]-Triazoloheteroarenes 对甲苯磺酰肼与n -杂芳酮的可切换反应：n -杂芳醇和[1,2,3]-三唑杂芳烯的碱控制选择性合成
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-06-16 DOI: 10.1002/ajoc.202500408
Yifei Wu, Rurong Yu, Feiyue Hao, Zhengneng Jin, Jiashou Wu
{"title":"Switchable Reaction of p-Toluenesulfonyl Hydrazide With N-Heteroaryl Ketones: Base-Controlled Selective Synthesis of N-Heteroaryl Alcohols and [1, 2, 3]-Triazoloheteroarenes","authors":"Yifei Wu,&nbsp;Rurong Yu,&nbsp;Feiyue Hao,&nbsp;Zhengneng Jin,&nbsp;Jiashou Wu","doi":"10.1002/ajoc.202500408","DOIUrl":"10.1002/ajoc.202500408","url":null,"abstract":"<p>A novel switchable reaction of <i>p</i>-toluenesulfonyl hydrazide with <i>N</i>-heteroaryl ketones has been developed to synthesize <i>N</i>-heteroaryl alcohols and [1, 2, 3]-triazoloheteroarenes. <i>p</i>-Toluenesulfonyl hydrazide was found to be an efficient reducing agent for <i>N</i>-heteroaryl ketones in the presence of Et<sub>3</sub>N. A cascade cyclization reaction occurred when NaOH was applied as a base.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 8","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144832678","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
Structural Engineering of Platinum-Containing Organic Photovoltaic Catalysts for Solar-Driven Hydrogen Production: A Review 太阳能制氢用含铂有机光伏催化剂的结构工程研究进展
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-06-16 DOI: 10.1002/ajoc.202500402
Jianan Fan, Rong Fan, Dr. Po Sun, Dr. Hua Sun, Qichun Zhang
{"title":"Structural Engineering of Platinum-Containing Organic Photovoltaic Catalysts for Solar-Driven Hydrogen Production: A Review","authors":"Jianan Fan,&nbsp;Rong Fan,&nbsp;Dr. Po Sun,&nbsp;Dr. Hua Sun,&nbsp;Qichun Zhang","doi":"10.1002/ajoc.202500402","DOIUrl":"10.1002/ajoc.202500402","url":null,"abstract":"<p>Over the past five years, donor/acceptor (D/A) bulk heterojunction (BHJ) photocatalysts, leveraging organic photovoltaic (OPV) materials, have witnessed remarkable progress in photocatalytic water splitting for hydrogen production. By integrating donor and acceptor materials with complementary absorption spectra, D/A BHJ photocatalysts achieve broad-spectrum light harvesting spanning from ultraviolet to near-infrared wavelengths. The nanoscale phase separation between donor and acceptor domains ensures efficient exciton dissociation, thereby enhancing solar energy conversion efficiency. In this mini-review, we explore how structural engineering strategies can transform high-performance OPV materials into efficient photocatalysts. Additionally, we highlight current challenges and provide forward-looking insights into three critical areas: hydrogen evolution rates, long-term stability, and cost-effectiveness.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 8","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144832680","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
Cyclotetrabenzil Oxime Derivatives 环四苯二肟衍生物
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-06-16 DOI: 10.1002/ajoc.202500521
Thusini P. Hemachandra, Bhawna Kumari, Yun-Hsien Lin, Ashikur Rabbi, Thamon Puangsamlee, Xiqu Wang, Soumya Mukherjee, Ognjen Š. Miljanić
{"title":"Cyclotetrabenzil Oxime Derivatives","authors":"Thusini P. Hemachandra,&nbsp;Bhawna Kumari,&nbsp;Yun-Hsien Lin,&nbsp;Ashikur Rabbi,&nbsp;Thamon Puangsamlee,&nbsp;Xiqu Wang,&nbsp;Soumya Mukherjee,&nbsp;Ognjen Š. Miljanić","doi":"10.1002/ajoc.202500521","DOIUrl":"10.1002/ajoc.202500521","url":null,"abstract":"<p>Cyclotetrabenzil, a shape-persistent macrocyclic octaketone, is found to undergo eightfold condensation with hydroxylamine hydrochloride to yield its octaoxime. Subsequent acetylation of this macrocyclic oxime afforded the corresponding octaoxime acetate. Single-crystal X-ray diffraction reveals that both new derivatives assemble into nanotubular structures. However, their packing differs: the oxime forms hydrogen-bonded tubes that bundle via included dimethyl sulfoxide (DMSO) molecules, whereas the acetate—lacking hydrogen-bond donors—forms more loosely packed tubes with molecules tilted ∼54.5° relative to the tube axis. Gas sorption studies (CO<sub>2</sub>, C<sub>2</sub>, and C<sub>3</sub> hydrocarbons) show that cyclotetrabenzil is nonporous, whereas the oxime and acetate exhibit modest microporosity with BET surface areas of ∼200 m<sup>2</sup> g<sup>−1</sup>. Both derivatives display preferential uptake of propyne over propene and propane, and the acetate also adsorbs more acetylene than ethylene or ethane. Nonetheless, these capacities and selectivities are suboptimal for dynamic separation of C<sub>2</sub> and C<sub>3</sub> hydrocarbons. This study illustrates how oxime functionalization can modulate macrocyclic assembly and gas uptake behavior, providing insights for the design of future porous organic macrocycles.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 8","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144832677","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
Amino Acid Derived Hydrogen Bond Donor (HBD) Catalyst for the Synthesis of Cyclic Carbonates and Cyclic Dithiocarbonates: Experimental and Computational Studies 氨基酸衍生氢键供体（HBD）催化剂合成环碳酸盐和环二硫代碳酸盐：实验和计算研究
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-06-16 DOI: 10.1002/ajoc.202500244
Supratim Halder, Koushik Das, Saumik Sen, Dr. Sandipan Halder
{"title":"Amino Acid Derived Hydrogen Bond Donor (HBD) Catalyst for the Synthesis of Cyclic Carbonates and Cyclic Dithiocarbonates: Experimental and Computational Studies","authors":"Supratim Halder,&nbsp;Koushik Das,&nbsp;Saumik Sen,&nbsp;Dr. Sandipan Halder","doi":"10.1002/ajoc.202500244","DOIUrl":"10.1002/ajoc.202500244","url":null,"abstract":"<p>Amino acid derived functionalized compounds have been designed, synthesized, and utilized as hydrogen bond donor (HBD) catalysts for the successful installation of CO<sub>2</sub> and CS<sub>2</sub> in epoxide for the synthesis of corresponding cyclic carbonates and dithiocarbonates. Here, the structural features of the catalysts play pivotal role for the viable utilization of the C-1 synthons. The rational design of the HBD catalysts involved strategic derivatization of the amine group of the amino acid ester to cater suitable noncovalent interactions with the substrate epoxide. Suitable hydrogen bonding interactions take place between the purposefully incorporated phenolic −OH groups present in the catalysts and the “O” atom of the epoxide. The syntheses of such amino acid derivatives involve sequential functional group modifications with expedient reaction steps. The catalytic activity of such novel amino acid ester derivatives was studied for CO<sub>2</sub> and CS<sub>2</sub> installation reactions with various epoxides. Excellent results were obtained in terms of selectivity and yield of the final products. Tetra-butyl ammonium iodide (TBAI) was used as a cocatalyst and the reactions were optimized in a very mild and solvent free condition. Overall, this research work demonstrates effective implementation of newly developed HBD catalysts in the one-pot, multi-steps domino reaction protocol.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 8","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144832676","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 Feature: C3-Symmetric Chiral Cage-Shaped Phosphates: Synthesis and Application as Organocatalysts in Asymmetric Iodolactonizations (Asian J. Org. Chem. 6/2025) 3-对称手性笼形磷酸盐的合成及其在不对称碘化反应中的应用[j]。化学6/2025)
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-06-16 DOI: 10.1002/ajoc.202580602
Xiao Liu, Dr. Akihito Konishi, Prof. Dr. Makoto Yasuda
{"title":"Cover Feature: C3-Symmetric Chiral Cage-Shaped Phosphates: Synthesis and Application as Organocatalysts in Asymmetric Iodolactonizations (Asian J. Org. Chem. 6/2025)","authors":"Xiao Liu,&nbsp;Dr. Akihito Konishi,&nbsp;Prof. Dr. Makoto Yasuda","doi":"10.1002/ajoc.202580602","DOIUrl":"10.1002/ajoc.202580602","url":null,"abstract":"<p>The <i>C</i><sub>3</sub>-symmetric, cage-shaped phosphate creates a helical chiral environment that functions like a vortex with a single direction. When a linear starting material enters this chiral environment, it is transformed into a precisely controlled stereochemical product. This transformation represents how the chiral vortex causes a dragon to curl up into a coil! The cover image depicts the dragon's transformation, which is catalyzed by our vortex-shaped catalyst. More details can be found in article number e202500299 by Xiao Liu, Akihito Konishi, and Makoto Yasuda. \u0000\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure></p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 6","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202580602","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144292626","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
Base-Metal-Catalyzed Oxidative Cross-Couplings Between 2-Naphthols and Phenols or Arylamines 碱金属催化的2-萘酚与酚或芳胺之间的氧化交叉偶联
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-06-14 DOI: 10.1002/ajoc.202500367
Qi Liu, Mengyu Liu, Bowen Xiao, Yangkai Xia, Yongqi Tian, Wenfeng Wang, Liuhui Xu, Hong Yan
{"title":"Base-Metal-Catalyzed Oxidative Cross-Couplings Between 2-Naphthols and Phenols or Arylamines","authors":"Qi Liu,&nbsp;Mengyu Liu,&nbsp;Bowen Xiao,&nbsp;Yangkai Xia,&nbsp;Yongqi Tian,&nbsp;Wenfeng Wang,&nbsp;Liuhui Xu,&nbsp;Hong Yan","doi":"10.1002/ajoc.202500367","DOIUrl":"10.1002/ajoc.202500367","url":null,"abstract":"<p>An unprecedented base-metal-catalyzed oxidative cross-coupling between 2-naphthols and phenols or arylamines has been described in this report. Acetic acid and 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) are the crucial oxidative system that promotes the transformation under aerobic conditions with the assistance of base-metal salts. While ferrous sulfate was the optimal catalyst in the oxidative coupling of 2-naphthols and phenols to produce 4-aryloxynaphthalene-1,2-diones, cuprous iodide catalyst is utilized to synthesize (arylimino)naphthalen-1(4<i>H</i>)-ones from 2-naphthols and arylamines. Employing this protocol, molecule skeletons similar to tanshinones, 2-(2-carboxyvinyl)benzoic acid and neo-tanshinlactone can be accessed thus highlighting its potential use in organic synthesis and drug discovery.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 8","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144832911","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
Grindstone Telescopic Approach for Pyrrolodiazepines Through Pictet-Spengler-Type Reaction and Solvent-Free Synthesis of Quinazolines pictet - spengler型反应与无溶剂合成吡咯二氮卓类药物的磨石伸缩法
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-06-14 DOI: 10.1002/ajoc.202500118
Maitreyee Panda, Dr. Anirban Bera, Dibas Dandapat, Paritosh Barik, Dr. Shubhendu Dhara, Dr. Mohammed Ikbal, Kuheli Pramanik, Dr. Smritimoy Pramanik, Dr. Shubhankar Samanta
{"title":"Grindstone Telescopic Approach for Pyrrolodiazepines Through Pictet-Spengler-Type Reaction and Solvent-Free Synthesis of Quinazolines","authors":"Maitreyee Panda,&nbsp;Dr. Anirban Bera,&nbsp;Dibas Dandapat,&nbsp;Paritosh Barik,&nbsp;Dr. Shubhendu Dhara,&nbsp;Dr. Mohammed Ikbal,&nbsp;Kuheli Pramanik,&nbsp;Dr. Smritimoy Pramanik,&nbsp;Dr. Shubhankar Samanta","doi":"10.1002/ajoc.202500118","DOIUrl":"10.1002/ajoc.202500118","url":null,"abstract":"<p>Hypervalent iodine activated Pictet-Spengler-type telescoping strategy under grindstone technology has been reported for the first time to construct pyrrolodiazepine with minimum E-factor. The same hypervalent iodine is also applicable to the synthesis of quinazoline cores in moderate to excellent yields under neat conditions. This greener approach for <i>N</i>-centered heterocycles is superior compare to the traditional methods due to its shorter reaction time, eco-friendly conditions, reduced cost, lower energy consumption, higher yields of desired products, and broader substrate scope. The scale-up experiment for the Pictet–Spengler-type reaction and the extension of protocol to the Bischler–Napieralski reaction give a new feather of the sustainable chemistry.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 8","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144832910","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
Large-Scale Chemoenzymatic Synthesis of a Glycophorin A Tetrasaccharide Motif and Its Analogues 糖蛋白a四糖基序及其类似物的大规模化学酶合成
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-06-14 DOI: 10.1002/ajoc.202500057
Ivan A. Gagarinov, Kam Lau, Robin J. Thomson, Thomas Haselhorst, Ross L. Coppel, Mark von Itzstein
{"title":"Large-Scale Chemoenzymatic Synthesis of a Glycophorin A Tetrasaccharide Motif and Its Analogues","authors":"Ivan A. Gagarinov,&nbsp;Kam Lau,&nbsp;Robin J. Thomson,&nbsp;Thomas Haselhorst,&nbsp;Ross L. Coppel,&nbsp;Mark von Itzstein","doi":"10.1002/ajoc.202500057","DOIUrl":"10.1002/ajoc.202500057","url":null,"abstract":"<p>A large-scale chemoenzymatic methodology has been developed to prepare a natural and substituted analogues of the Glycophorin A tetrasaccharide, in which the α-2,3-sialic acid is modified at either C5 or C9 either as F, OMe, CH<sub>3</sub>, glycolyl or N<sub>3</sub>. The strategy involved a chemical synthesis of a Gal-β-1,3-GalNAc disaccharide in which the galactose remains acetylated to first enable selective α-2,6-sialylation using a one-pot aldolase-NmCSS-Pd2,6-ST enzyme system. Finally, C5 or C9 modifed α-2,3 sialosides were placed at the galactoside moiety using C2 or C6 modified MaNAc derivatives catalyzed by aldolase NmCSS-Pd2,3-ST enzyme combination. The synthesised molecules can be useful in binding studies with a protein of interest or as an entry point to establish a library of analytical samples for mass-spectrometric studies.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 8","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://aces.onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202500057","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144832912","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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