Carbohydrate Research最新文献_第2页

IgG galactosylation changes in cancer. IgG半乳糖基化在癌症中的变化。

IF 2.5 3区化学

Carbohydrate Research Pub Date : 2025-09-22 DOI: 10.1016/j.carres.2025.109681

Yumeng Liu, Xiequn Xu, Zejian Zhang

{"title":"IgG galactosylation changes in cancer.","authors":"Yumeng Liu, Xiequn Xu, Zejian Zhang","doi":"10.1016/j.carres.2025.109681","DOIUrl":"https://doi.org/10.1016/j.carres.2025.109681","url":null,"abstract":"<p><p>The incidence and mortality rates of cancer continue to rise globally. To facilitate earlier diagnosis and treatment, and thereby improve the survival outcomes for cancer patients, numerous detection methods have been employed into clinical practice. Glycosylation, a common biological regulatory process, plays a key role in both physiological and pathological processes. Glycans are oligosaccharides composed of a variety of monosaccharides, and galactose is an important terminal structure of glycans. Notably, increased agalactosylated IgG is commonly associated with the occurrence and progression of cancers; however, the clinical utility of IgG galactosylation in cancer remains a contentious topic. This review summarizes current evidence on alternations in serum and plasma IgG galactosylation in cancer patients, discusses potential mechanisms underlying these changes, and highlights future use in cancer detection, diagnosis, and prognosis. Overall, IgG galactosylation holds significant promise not only for the diagnosis of malignant tumors but also for distinguishing between benign and malignant tumors, cancer staging and monitoring progression. IgG galactosylation could serve as a complementary parameter to existing cancer markers, thereby contributing to more precise and timely diagnosis and treatment of cancers.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"558 ","pages":"109681"},"PeriodicalIF":2.5,"publicationDate":"2025-09-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145198396","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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

Effective removal of Rhodamine B dye using novel benzoxazine-crosslinked magnetic chitosan 新型苯并恶嗪交联磁性壳聚糖对罗丹明B染料的有效去除

IF 2.5 3区化学

Carbohydrate Research Pub Date : 2025-09-22 DOI: 10.1016/j.carres.2025.109677

Noura N. Eltahan , H.H. Abdel-Razik , Fathy M. El-Taweel , Magdy Y. Abdelaal

{"title":"Effective removal of Rhodamine B dye using novel benzoxazine-crosslinked magnetic chitosan","authors":"Noura N. Eltahan , H.H. Abdel-Razik , Fathy M. El-Taweel , Magdy Y. Abdelaal","doi":"10.1016/j.carres.2025.109677","DOIUrl":"10.1016/j.carres.2025.109677","url":null,"abstract":"<div><div>Water pollution and dye contamination pose serious environmental challenges, necessitating the development of efficient and sustainable adsorbent materials. In this study, we report a novel magnetic Chitosan-based nanocomposite synthesized by functionalization with 2-hydroxy-1,4-benzoxazine, glutaraldehyde crosslinking, and Fe<sub>3</sub>O<sub>4</sub> incorporation Ch-BOX/Glu/Fe<sub>3</sub>O<sub>4</sub> for the removal of Rhodamine B dye. Comprehensive characterization FTIR, HNMR, XRD, SEM, TEM, TGA, EDX confirmed the successful modification, with Fe<sub>3</sub>O<sub>4</sub> particle size of 10.4 nm and enhanced thermal stability T<sub>50</sub> = 420 °C. Under optimized conditions 0.5 g adsorbent dose, 20 mg/L initial dye concentration, 25 °C, 3 days, the maximum dye removal efficiency reached 81.3 % for Ch-BOX/Glu and 79.7 % for Ch-BOX/Glu/Fe<sub>3</sub>O<sub>4</sub>. Kinetic analysis revealed that the adsorption followed a pseudo-second-order model R<sup>2</sup> = 0.99, confirming chemisorption. Reusability tests demonstrated that Ch-BOX/Glu retained 60 % removal efficiency after 3 cycles, while Ch-BOX/Glu/Fe<sub>3</sub>O<sub>4</sub> retained 35 %, indicating comparatively higher long-term stability for the non-magnetic composite. This work introduces an innovative Chitosan-benzoxazine-magnetite hybrid platform that combines structural stability, efficient dye removal, and recyclability, highlighting its potential for future wastewater treatment applications.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"558 ","pages":"Article 109677"},"PeriodicalIF":2.5,"publicationDate":"2025-09-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145109829","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 characteristics of two pectic polysaccharides from Avicennia marina fruit. 海棠果实两种果胶多糖的结构特征。

IF 2.5 3区化学

Carbohydrate Research Pub Date : 2025-09-22 DOI: 10.1016/j.carres.2025.109679

Huaqun Chen, Wennian Li, Chunyu Xiao, Xiaotao Hou, Kefeng Wu, Longyan Zhao, Qingxia Yuan

{"title":"Structural characteristics of two pectic polysaccharides from Avicennia marina fruit.","authors":"Huaqun Chen, Wennian Li, Chunyu Xiao, Xiaotao Hou, Kefeng Wu, Longyan Zhao, Qingxia Yuan","doi":"10.1016/j.carres.2025.109679","DOIUrl":"https://doi.org/10.1016/j.carres.2025.109679","url":null,"abstract":"<p><p>Pectic polysaccharides in A. marina fruit exhibit excellent prebiotic effects and may be the key to treating constipation and dysentery; however, their detailed structures still need to be clarified. In this study, we obtained two pectic polysaccharide fractions (AMFPs-3-2 and AMFPs-3-4) from this fruit for the first time and comprehensively investigated their fine structures using chemical methods, GC-MS, and 1D and 2D-NMR. AMFPs-3-2 was identified as a type I rhamnogalacturonan (RG-I) with a backbone composed of →2)-α-Rhap-(1 → 4)-α-GalpA-(1→, and the side chains mainly consisted of arabinan with non-reducing ends of α/β-Araf. Meanwhile, AMFPs-3-4 was characterized as a homogalacturonan (HG) composed of galacturonic acid (GalpA) and methyl-esterified GalpA, with GalpA, (un)saturated GalpA and methyl-esterified (un)saturated GalpA as non-reducing ends, and α/β-GalpA or methyl-esterified α/β-GalpA as reducing ends. These findings demonstrate that different types of pectic polysaccharides from A. marina fruit can be effectively separated and distinguished. The elucidation of these clear structural features provides a solid structural basis for further investigating the pharmacological activity and structure-activity relationship of polysaccharides from A. marina fruit.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"558 ","pages":"109679"},"PeriodicalIF":2.5,"publicationDate":"2025-09-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145198399","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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

Understanding meningococcal X unconjugated saccharide behaviour in monovalent and pentavalent (A, C, Y, W and X) conjugate formulations for quality analysis of meningococcal conjugate vaccine. 了解单价和五价（A、C、Y、W和X）脑膜炎球菌X非偶联糖的行为，用于脑膜炎球菌结合疫苗的质量分析。

IF 2.5 3区化学

Carbohydrate Research Pub Date : 2025-09-20 DOI: 10.1016/j.carres.2025.109678

Swapnil Phugare, Abhijit Patil, Sameer Kale, Pankaj Sharma, Sunil Kumar Goel, Sunil Gairola

{"title":"Understanding meningococcal X unconjugated saccharide behaviour in monovalent and pentavalent (A, C, Y, W and X) conjugate formulations for quality analysis of meningococcal conjugate vaccine.","authors":"Swapnil Phugare, Abhijit Patil, Sameer Kale, Pankaj Sharma, Sunil Kumar Goel, Sunil Gairola","doi":"10.1016/j.carres.2025.109678","DOIUrl":"https://doi.org/10.1016/j.carres.2025.109678","url":null,"abstract":"<p><p>The pentavalent meningococcal polysaccharide conjugate vaccine, which includes serogroup A, C, Y, W, and X, has recently been prequalified by the WHO and is currently the only vaccine available against serogroup X. The amount of free saccharide in conjugate vaccines is a crucial factor that directly impacts the stability and immunogenicity of the vaccine. Therefore, precise estimation of free saccharide content is particularly important in multivalent conjugate vaccines. This study focuses on the development of conditions for estimating free saccharide in monovalent meningococcal X conjugate bulk. Accuracies were demonstrated at 5 %, 10 %, 25 %, and 40 % of the test specification, with recoveries ranging from 70 to 130 %. Repeatability analysis showed intra-assay variation ranging from 2 to 6 %, while inter-assay variation ranged from 2 to 14 %. Specificity studies indicated that there was no interference from assay components such as sample excipients, DOC, or acids. When these established conditions were applied to the finished product for free saccharide estimation, an interesting observation was noted. It was found that the unconjugated meningococcal X saccharide interacted with other biomolecules present in the vaccine formulation, leading to decreased free saccharide recovery for serogroup X. It is believed that aggregation, possibly due to carrier proteins (TT and CRM) and/or associated polysaccharides, may be responsible for trapping the free saccharide from serogroup X. Efforts were made to control these biomolecular interactions by adjusting solubilities, buffering, and physico-chemical conditions to separate free saccharide. Phosphate buffers, ionic-nonionic detergent solutions, salt buffers, and 32 biomolecule formulations were explored in various combinations before identifying the root cause for the decreased X free saccharide recoveries.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"558 ","pages":"109678"},"PeriodicalIF":2.5,"publicationDate":"2025-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145184671","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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

Identification of O-GalNAc-modified proteins interacting with GALNT3 using proximity labeling method 利用接近标记法鉴定与GALNT3相互作用的o - galnac修饰蛋白

IF 2.5 3区化学

Carbohydrate Research Pub Date : 2025-09-20 DOI: 10.1016/j.carres.2025.109675

Bo Xu , Mingzhu Zhang , You Yu , Mengjiao Yang , Zhenwang Zhang , Mingjie Wei , Shigang Shan , He Zhu , Yanting Su

{"title":"Identification of O-GalNAc-modified proteins interacting with GALNT3 using proximity labeling method","authors":"Bo Xu , Mingzhu Zhang , You Yu , Mengjiao Yang , Zhenwang Zhang , Mingjie Wei , Shigang Shan , He Zhu , Yanting Su","doi":"10.1016/j.carres.2025.109675","DOIUrl":"10.1016/j.carres.2025.109675","url":null,"abstract":"<div><div>Protein glycosylation is a widely occurring post-translational modification catalyzed by glycosyltransferases and is involved in various biological functions. O– N-acetylgalactosamine (O-GalNAc) modification is catalyzed by the N-acetylgalactosaminyltransferase (GALNT) family and represents a truncated form of O-glycosylation, which is closely associated with the development of various diseases. The O-GalNAc modification has long been considered to occur exclusively within the secretory pathway, targeting only membrane and secreted proteins. However, recent study has reported the nuclear localization of GALNT3, suggesting that O-GalNAc modification can also occur in the nucleus. Currently, there is no comprehensive glycoproteomic characterization of O-GalNAc modifications in the nucleus. Here, we employed an efficient proximity labeling approach based on a mutant biotin ligase, TurboID. By generating a fusion of GALNT3 with TurboID, biotin labeling was performed in living cells, enabling the biotinylation of proteins that interact with GALNT3. Using this strategy, delineated 25 high-confidence and 10 potential O-GalNAc-modified sites across 26 characterized proteins and 4 uncharacterized proteins. Additionally, 52 putative O-GalNAc-modified peptides originating from 33 distinct proteins and 19 uncharacterized proteins were identified. The majority of which were nuclear-localized and reported to be O-GalNAc-modified for the first time.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"558 ","pages":"Article 109675"},"PeriodicalIF":2.5,"publicationDate":"2025-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145119093","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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

Molecular regulation mechanism of two glycosyltransferases in exopolysaccharide biosynthesis of Lactiplantibacillus plantarum YM-4-3 strain 植物乳杆菌YM-4-3菌株胞外多糖合成过程中两种糖基转移酶的分子调控机制

IF 2.5 3区化学

Carbohydrate Research Pub Date : 2025-09-18 DOI: 10.1016/j.carres.2025.109676

Zhen Zhang , Bo Zhao , Yonggang Xiong , Xiaoran Li , Chenjian Liu , Junwei Xu , Jinping Yan , En Yang

{"title":"Molecular regulation mechanism of two glycosyltransferases in exopolysaccharide biosynthesis of Lactiplantibacillus plantarum YM-4-3 strain","authors":"Zhen Zhang , Bo Zhao , Yonggang Xiong , Xiaoran Li , Chenjian Liu , Junwei Xu , Jinping Yan , En Yang","doi":"10.1016/j.carres.2025.109676","DOIUrl":"10.1016/j.carres.2025.109676","url":null,"abstract":"<div><div>Exopolysaccharide (EPS) is a high molecular weight polymer produced by lactic acid bacteria (LAB) during their growth and metabolism. Due to the genetic diversity of strains and the structural diversity of EPS, it exhibits a variety of physiological activities and has potential applications in food, medicine, agriculture, and other fields. This study focuses on two glycosyltransferases (<em>orf</em>1595 and <em>cps</em>4I) involved in the synthesis of oligosaccharide repeat units in the EPS biosynthesis by <em>Lactiplantibacillus plantarum</em> YM-4-3 strain. These enzymes are key to polysaccharide synthesis. By knocking out and complementing the <em>orf</em>1595 and <em>cps</em>4I genes, combined with transcriptome analysis, we preliminarily determined their functions. The results showed that EPS yield decreased significantly after the gene knockout but was restored after complementation. Transcriptome sequencing revealed that knockout of these glycosyltransferase genes led to differential expression of genes within the EPS synthesis cluster and affected sugar metabolism pathways. Furthermore, EPS antioxidant activity was significantly altered: DPPH radical and superoxide anion scavenging abilities decreased, while hydroxyl radical scavenging increased. Chemical analysis indicated changes in EPS protein, glucuronic acid, and sulfate contents after knockout. This study clarifies the critical roles of <em>orf</em>1595 and <em>cps</em>4I in EPS biosynthesis by <em>L. plantarum</em> YM-4-3, providing a theoretical basis for regulating EPS synthesis and facilitating the development of LAB EPS with diverse physiological activities.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"558 ","pages":"Article 109676"},"PeriodicalIF":2.5,"publicationDate":"2025-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145106505","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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

Application prospect of Marine polysaccharide hydrogels in promoting wound healing: A review 海洋多糖水凝胶在促进伤口愈合中的应用前景综述

IF 2.5 3区化学

Carbohydrate Research Pub Date : 2025-09-17 DOI: 10.1016/j.carres.2025.109673

Yujie Liu , Jiarui Liu , Aijia Zhang , Guiyuan Zhao , Bolong Jiang , Xia Zhao

引用次数: 0

Preparation and characterization of polysaccharide-derived smart nanocarriers for stimuli-responsive delivery of natural extracts in NSCLC therapy 用于非小细胞肺癌治疗中天然提取物刺激反应递送的多糖衍生智能纳米载体的制备和表征。

IF 2.5 3区化学

Carbohydrate Research Pub Date : 2025-09-14 DOI: 10.1016/j.carres.2025.109670

Pengxiao Hou , Chaowei Tang , Wei Zhao , Zhilong Li

{"title":"Preparation and characterization of polysaccharide-derived smart nanocarriers for stimuli-responsive delivery of natural extracts in NSCLC therapy","authors":"Pengxiao Hou , Chaowei Tang , Wei Zhao , Zhilong Li","doi":"10.1016/j.carres.2025.109670","DOIUrl":"10.1016/j.carres.2025.109670","url":null,"abstract":"<div><div>Non-small cell lung cancer (NSCLC) has a poor prognosis due to late diagnosis and high metastasis, while existing agents like Cucurbitaceae-derived Compound 1 are limited by low solubility, poor targeting, and high normal cell toxicity. This study aimed to construct a fluorinated hyaluronic acid nanocarrier (HA-2@1) to load Compound 1, improving its solubility/biocompatibility, enabling NSCLC-targeted delivery, and enhancing therapeutic efficacy. In vitro experiments included pH-responsive drug release testing, fluorescence spectroscopy for carrier-drug interactions, and CCK-8 cytotoxicity assays on A549 (NSCLC) and BEAS-2B (normal lung) cells, compared with free Compound 1. Results showed: HA-2@1 released 75 % of Compound 1 at pH 5.0 (tumor microenvironment) vs. 43 % at pH 7.4 (physiological condition) within 120 h; Compound 1 loading reduced HA-2 fluorescence by 26 % (intermolecular quenching) with further aggregation-driven quenching at 100 μg/mL; HA-2@1 decreased A549 viability by 25 % at 48 h, and its toxicity to BEAS-2B cells (7 % at 200 μg/mL) was far lower than free Compound 1 (53 %). In conclusion, HA-2@1 offers targeted delivery, fluorescence tracking, low toxicity, and efficient release, providing a promising nano-strategy for NSCLC therapy and a reference for natural product carrier optimization.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"558 ","pages":"Article 109670"},"PeriodicalIF":2.5,"publicationDate":"2025-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145102597","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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

Smart-responsive dual cross-linked chitooligosaccharide nanoparticles with high stability and ROS-triggered self-accelerating drug release for enhanced breast cancer therapy 具有高稳定性和ros触发的自加速药物释放的智能响应双交联壳寡糖纳米颗粒用于增强乳腺癌治疗。

IF 2.5 3区化学

Carbohydrate Research Pub Date : 2025-09-13 DOI: 10.1016/j.carres.2025.109671

Yuting Sun , Junnan He , Yongyan Sun , Lidong Wang , Haidu Li , Yaqi Miao , Ping Shi , Jin Zhang , Kaixuan Luo , Yan Zhao

{"title":"Smart-responsive dual cross-linked chitooligosaccharide nanoparticles with high stability and ROS-triggered self-accelerating drug release for enhanced breast cancer therapy","authors":"Yuting Sun , Junnan He , Yongyan Sun , Lidong Wang , Haidu Li , Yaqi Miao , Ping Shi , Jin Zhang , Kaixuan Luo , Yan Zhao","doi":"10.1016/j.carres.2025.109671","DOIUrl":"10.1016/j.carres.2025.109671","url":null,"abstract":"<div><div>The development of reactive oxygen species (ROS)-responsive nanodrug delivery systems faces critical challenges. Excessive cross-linking degree prevents complete degradation of nanocarriers under tumor microenvironment ROS levels, significantly compromising drug release efficiency. Conversely, insufficient cross-linking degree impairs the structural stability of nanoparticles, resulting in premature drug leakage during systemic administration. Herein, we present an innovative strategy for constructing dual cross-linked chitooligosaccharide nanoparticles (NPs) co-loaded with curcumin and glucose oxidase (GOx) to enhance structural stability. These engineered NPs can amplify intracellular ROS concentration through GOx-mediated catalytic conversion of glucose to H<sub>2</sub>O<sub>2</sub>, thereby establishing a ROS-triggered self-accelerating drug release nanosystem for enhanced tumor chemotherapy. <em>In vitro</em> studies have shown that the curcumin release behavior of CTCG NPs depends on the GOx encapsulated inside the nanoparticles. Compared with nanoparticles without GOx, CTCG NPs can effectively prevent the premature release of curcumin in a simulated normal physiological environment. The nanoparticles also showed significant anti-tumor effect and could effectively inhibit the proliferation of tumor cells in <em>vivo</em>. These results proved that CTCG NPs achieve controllable release of drugs through in situ production of ROS in the tumor microenvironment. This nanodrug delivery system shows promising potential for breast cancer therapy.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"558 ","pages":"Article 109671"},"PeriodicalIF":2.5,"publicationDate":"2025-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145085103","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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

Organocatalyzed synthesis of 2-deoxyglycosyl azides: Application in 1,2,3-triazole linked 2-deoxyglycosides 有机催化合成2-脱氧糖基叠氮化物：在1,2,3-三唑连接的2-脱氧糖苷中的应用。

IF 2.5 3区化学

Carbohydrate Research Pub Date : 2025-09-13 DOI: 10.1016/j.carres.2025.109668

Vivek Kumar Sharma , Rima Thakur

{"title":"Organocatalyzed synthesis of 2-deoxyglycosyl azides: Application in 1,2,3-triazole linked 2-deoxyglycosides","authors":"Vivek Kumar Sharma , Rima Thakur","doi":"10.1016/j.carres.2025.109668","DOIUrl":"10.1016/j.carres.2025.109668","url":null,"abstract":"<div><div>In comparison to the significant development of catalysed reactions for the formation of 2-deoxyglycoside from glycals, synthetic methods for the direct formation of 2-deoxyglycosyl azides are less explored. Consequently, the use of the 2-deoxy sugar moieties in the studies involving N-linked modified sugars for the advancements in bio-compatible materials and therapeutics are restricted despite the C2-hydroxylated glycosyl azides finding prominent application through glycodiversifications. We <em>herein</em> report an organocatalysed synthesis of 2-deoxyglycosyl azides from glycals using <em>N</em>-Fluorobezenesulfonimide (NFSI) as a catalyst and TEMPO as a co-catalyst in 1,2-DCE. The appropriate reaction conditions were determined by systematically varying reaction parameters and subsequently employed to the synthesis of glycosyl azides from differently protected glycals. The reactions did not suffer from Ferrier rearrangement by-product and was observed to be essentially <em>α</em>-selective in nature. Furthermore, the azides have been tested for the synthesis of 2-deoxy sugar linked 1,2,3-triazole derivatives using “click” reaction. Several alkynes with aromatic and aliphatic substitutions have been thus reacted with the azides to obtain a new class of 2-deoxyglycosides.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"558 ","pages":"Article 109668"},"PeriodicalIF":2.5,"publicationDate":"2025-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145091274","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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