A photo-assisted oligosaccharide assembly strategy is reported for the facile synthesis of a branched heptasaccharide with potential anti-panceratic cancer activity in a four-component [2 + 1 + 1 + 3] one-pot coupling manner. A key feature of this strategy is the incorporation of photocleavable o-nitrobenzyl group-protected saccharide building blocks. Upon exposure to ultraviolet radiation, these blocks can generate in situ the corresponding acceptors for subsequent glycosylations without the purification step, thereby facilitating the one-pot coupling process and enabling the rapid assembly of the heptasaccharide.
{"title":"Photo-assisted four-component one-pot assembly of a branched heptasaccharide derived from Carthamus tinctorius","authors":"Chaoyu Hu (Data curation Formal analysis Funding acquisition Methodology Validation Writing – original draft) , Ruixue Wu (Data curation Formal analysis Methodology Validation) , Xiang Ni (Data curation Formal analysis Methodology Validation) , Wenjing Ma (Formal analysis Validation Writing – review & editing) , Tianhui Hao (Formal analysis Validation Writing – review & editing) , Zhuojia Xu (Formal analysis Validation Writing – review & editing) , Kan Ding (Conceptualization Project administration Supervision Writing – review & editing) , Tiehai Li (Conceptualization Funding acquisition Investigation Methodology Project administration Supervision Writing – original draft Writing – review & editing)","doi":"10.1080/07328303.2025.2568841","DOIUrl":"10.1080/07328303.2025.2568841","url":null,"abstract":"<div><div>A photo-assisted oligosaccharide assembly strategy is reported for the facile synthesis of a branched heptasaccharide with potential anti-panceratic cancer activity in a four-component [2 + 1 + 1 + 3] one-pot coupling manner. A key feature of this strategy is the incorporation of photocleavable <em>o</em>-nitrobenzyl group-protected saccharide building blocks. Upon exposure to ultraviolet radiation, these blocks can generate <em>in situ</em> the corresponding acceptors for subsequent glycosylations without the purification step, thereby facilitating the one-pot coupling process and enabling the rapid assembly of the heptasaccharide.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"44 7","pages":"Pages 296-311"},"PeriodicalIF":2.2,"publicationDate":"2025-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145464852","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}
Pub Date : 2025-09-29DOI: 10.1080/07328303.2025.2564406
Projesh Saha (Resources Writing – original draft Writing – review & editing) , Bibhas Pandit (Conceptualization Supervision Writing – original draft Writing – review & editing) , Papiya Biswas (Resources Writing – original draft)
Cellulose is a polysaccharide composed of numerous glucose subunits connected by β-linkages. They are the richest sources of dietary fiber on Earth. Above all, elevated water solubility renders it an exceptional medium for amalgamating water-insoluble pharmaceuticals, such as enzymes and antibiotics. The presence of hydroxyl groups in each glucose unit affects the reactivity and applicability of cellulose to various pharmaceutical formulations. Diverse techniques, such as oxidation, amination, esterification and radical copolymerization, are usually adopted to modify these hydroxyl groups for improving the properties of cellulose. Chemically modified cellulose derivatives have been extensively used in the formulation of enteric-coated solid dosage forms, osmotic drug delivery systems, mucoadhesive and bio-adhesive drug delivery systems, and extended-release formulations. In addition, cellulose-based polymers also play various roles in pharmaceutical formulations, such as binding, filling, disintegrating, coating, gelling, thickening, stabilizing, and flavor-masking agents. The pharmaceutical industry has adopted cellulose-based polymers as significant components in the formulation, development, and production of new derivatives. The prevalence of cellulose-based polymers in pharmaceuticals has increased owing to continuous research that reveals new applications for chemically modified cellulose, as well as the development of new cellulose-based derivatives with optimized properties.
{"title":"Chemically modified cellulose: Chemistry, properties, and pharmaceutical applications","authors":"Projesh Saha (Resources Writing – original draft Writing – review & editing) , Bibhas Pandit (Conceptualization Supervision Writing – original draft Writing – review & editing) , Papiya Biswas (Resources Writing – original draft)","doi":"10.1080/07328303.2025.2564406","DOIUrl":"10.1080/07328303.2025.2564406","url":null,"abstract":"<div><div>Cellulose is a polysaccharide composed of numerous glucose subunits connected by β-linkages. They are the richest sources of dietary fiber on Earth. Above all, elevated water solubility renders it an exceptional medium for amalgamating water-insoluble pharmaceuticals, such as enzymes and antibiotics. The presence of hydroxyl groups in each glucose unit affects the reactivity and applicability of cellulose to various pharmaceutical formulations. Diverse techniques, such as oxidation, amination, esterification and radical copolymerization, are usually adopted to modify these hydroxyl groups for improving the properties of cellulose. Chemically modified cellulose derivatives have been extensively used in the formulation of enteric-coated solid dosage forms, osmotic drug delivery systems, mucoadhesive and bio-adhesive drug delivery systems, and extended-release formulations. In addition, cellulose-based polymers also play various roles in pharmaceutical formulations, such as binding, filling, disintegrating, coating, gelling, thickening, stabilizing, and flavor-masking agents. The pharmaceutical industry has adopted cellulose-based polymers as significant components in the formulation, development, and production of new derivatives. The prevalence of cellulose-based polymers in pharmaceuticals has increased owing to continuous research that reveals new applications for chemically modified cellulose, as well as the development of new cellulose-based derivatives with optimized properties.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"44 7","pages":"Pages 253-274"},"PeriodicalIF":2.2,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145464855","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}
Endo-β-N-acetylglucosaminidases (ENGases) cleave the N-glycan core from glycoproteins and are important tools for structural analysis of glycans. Currently, only a few ENGases can specifically cleave the complex-type N-glycans, highlighting the need for discovering novel ENGases for glycoengineering applications. Nevertheless, conventional techniques for ENGase analysis are limited by low throughput and a lack of real-time detection. Herein, we describe the development of a fluorescence quenching assay to measure the hydrolytic activity of ENGases against fucosylated and afucosylated biantennary complex-type N-glycans. Two chemically synthesized probes, MG2FD (1) and MG2D (2)—a decasaccharide and a nonasaccharide, respectively—were labeled with an N-methylanthraniloyl group (fluorophore) and a 2,4-dinitrophenyl group (quencher). These probes were used to evaluate commercially available ENGases: Endo-M, Endo-CC, Endo-F3, Endo-H, and Endo-S. Endo-M and Endo-CC selectively cleaved probe 2 but not probe 1; Endo-F3 cleaved only probe 1; however, Endo-H and Endo-S showed no detectable activity. These findings align with known substrate specificities, validating the assay as a rapid and reliable method for assessing ENGase activity, profiling substrate specificity, and identifying novel ENGases targeting complex-type glycans.
Endo-β- n -乙酰氨基葡萄糖酶（Endo-β-N-acetylglucosaminidases, ENGases）用于从糖蛋白中切割n -聚糖核，是分析糖蛋白结构的重要工具。目前，只有少数engase能够特异性地切割复杂型n -聚糖，这表明需要发现用于糖工程应用的新型engase。然而，传统的ENGase分析技术受到低通量和缺乏实时检测的限制。在这里，我们描述了一种荧光猝灭法的发展，以测量engase对聚焦和聚焦双触角络合型n -聚糖的水解活性。两种化学合成的探针MG2FD(1)和MG2D(2)分别是十糖和非糖，分别用n -甲基蒽醌基（荧光团）和2,4-二硝基苯基（猝灭剂）标记。这些探针用于评价市售的酶：Endo-M、Endo-CC、Endo-F3、Endo-H和Endo-S。Endo-M和Endo-CC可选择性切割探针2，但不能切割探针1；Endo-F3只裂解探针1；然而，Endo-H和Endo-S没有检测到活性。这些发现与已知的底物特异性一致，验证了该方法作为评估ENGase活性、分析底物特异性和鉴定靶向复合物型聚糖的新型ENGase的快速可靠方法。
{"title":"Fluorogenic probes for assessing endo-β-N-acetylglucosaminidase activity on complex-type N-glycans","authors":"Nozomi Ishii (Conceptualization Data curation Funding acquisition Investigation Methodology Project administration Resources Supervision Validation Writing – original draft Writing – review & editing) , Kenta Iino (Data curation Investigation Validation Writing – review & editing) , Yuji Matsuzaki (Project administration Resources Supervision Writing – review & editing) , Ichiro Matsuo (Conceptualization Funding acquisition Methodology Project administration Resources Supervision Writing – original draft Writing – review & editing)","doi":"10.1080/07328303.2025.2558652","DOIUrl":"10.1080/07328303.2025.2558652","url":null,"abstract":"<div><div>Endo-β-<em>N</em>-acetylglucosaminidases (ENGases) cleave the <em>N</em>-glycan core from glycoproteins and are important tools for structural analysis of glycans. Currently, only a few ENGases can specifically cleave the complex-type <em>N</em>-glycans, highlighting the need for discovering novel ENGases for glycoengineering applications. Nevertheless, conventional techniques for ENGase analysis are limited by low throughput and a lack of real-time detection. Herein, we describe the development of a fluorescence quenching assay to measure the hydrolytic activity of ENGases against fucosylated and afucosylated biantennary complex-type <em>N</em>-glycans. Two chemically synthesized probes, MG2FD (<strong>1</strong>) and MG2D (<strong>2</strong>)—a decasaccharide and a nonasaccharide, respectively—were labeled with an <em>N</em>-methylanthraniloyl group (fluorophore) and a 2,4-dinitrophenyl group (quencher). These probes were used to evaluate commercially available ENGases: Endo-M, Endo-CC, Endo-F3, Endo-H, and Endo-S. Endo-M and Endo-CC selectively cleaved probe <strong>2</strong> but not probe <strong>1</strong>; Endo-F3 cleaved only probe <strong>1</strong>; however, Endo-H and Endo-S showed no detectable activity. These findings align with known substrate specificities, validating the assay as a rapid and reliable method for assessing ENGase activity, profiling substrate specificity, and identifying novel ENGases targeting complex-type glycans.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"44 7","pages":"Pages 275-295"},"PeriodicalIF":2.2,"publicationDate":"2025-09-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145464857","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}
Pub Date : 2025-08-30DOI: 10.1080/07328303.2025.2551505
Ganesan Krishnamoorthy , Hari Sharan Adhikari , Govindarajan Krishnamoorthy
This work aims to design a stimuli-responsive photosensitizer chlorin e6 (Ce6)-coated stromal-cell-derived factor-1α (SDF-1α)-enclosed chitosan nanoparticles (Ce6-CNs-SDF-1α) by the ionotropic gelation method and investigate its photocontrol sustained-release properties by using near-infrared (NIR) light. The studies highlight these Ce6-CNs-SDF-1α fine particles with a size of 90–135 nm, charge of −32 ± 0.7 mV, and a spherical shape and smooth surface morphology. The positively charged chitosan and negatively charged tripolyphosphate (TPP) interaction along with SDF-1α and Ce6 was based on electrostatic interface between protonated amino and deprotonated phosphate groups. The photoinduced singlet oxygen generation (SOG), in which the ground state triplet oxygen (3O2) was excited into higher energy state singlet oxygen (1O2) as a result of energy transfer, was determined by the p-nitrosodimethylaniline (RNO) method with 660 nm irradiation. This indicated that the therapeutic activities were not changed after Ce6 being enclosed with CNs. The investigation comprised the Ce6 and SDF-1α releases from Ce6-CNs-SDF-1α as a function of time at pH 7.2. These compounds were found to have greater biocompatibility and no cytotoxicity as evaluated with the fibroblast cell lines from human skin by Alamar Blue assay and observed by confocal images. These smart NIR-responsive CNs can have potential uses in light-driven SDF-1α delivery for various diseases.
{"title":"Synthesis of SDF-1α-loaded chitosan nanoparticles coated with photosensitizer chlorin e6 for smart near IR light-controlled drug release","authors":"Ganesan Krishnamoorthy , Hari Sharan Adhikari , Govindarajan Krishnamoorthy","doi":"10.1080/07328303.2025.2551505","DOIUrl":"10.1080/07328303.2025.2551505","url":null,"abstract":"<div><div>This work aims to design a stimuli-responsive photosensitizer chlorin e6 (Ce6)-coated stromal-cell-derived factor-1α (SDF-1α)-enclosed chitosan nanoparticles (Ce6-CNs-SDF-1α) by the ionotropic gelation method and investigate its photocontrol sustained-release properties by using near-infrared (NIR) light. The studies highlight these Ce6-CNs-SDF-1α fine particles with a size of 90–135 nm, charge of −32 ± 0.7 mV, and a spherical shape and smooth surface morphology. The positively charged chitosan and negatively charged tripolyphosphate (TPP) interaction along with SDF-1α and Ce6 was based on electrostatic interface between protonated amino and deprotonated phosphate groups. The photoinduced singlet oxygen generation (SOG), in which the ground state triplet oxygen (<sup>3</sup>O<sub>2</sub>) was excited into higher energy state singlet oxygen (<sup>1</sup>O<sub>2</sub>) as a result of energy transfer, was determined by the <em>p</em>-nitrosodimethylaniline (RNO) method with 660 nm irradiation. This indicated that the therapeutic activities were not changed after Ce6 being enclosed with CNs. The investigation comprised the Ce6 and SDF-1α releases from Ce6-CNs-SDF-1α as a function of time at pH 7.2. These compounds were found to have greater biocompatibility and no cytotoxicity as evaluated with the fibroblast cell lines from human skin by Alamar Blue assay and observed by confocal images. These smart NIR-responsive CNs can have potential uses in light-driven SDF-1α delivery for various diseases.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"44 7","pages":"Pages 341-360"},"PeriodicalIF":2.2,"publicationDate":"2025-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145464853","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}
Pub Date : 2025-08-29DOI: 10.1080/07328303.2025.2552365
Mei Chen (Investigation) , Bangxing Hao (Investigation) , Liran Yang (Investigation) , Feiyan Xie (Investigation) , Panpan Wang (Investigation) , Peifan Xu (Investigation) , Jingyang Wei (Investigation) , Jimin Xu (Investigation) , Yugen Zhu (Supervision Writing – original draft)
8-Iodo-1-naphthoate is a key intermediate for the versatile preparation of 1,8-difunctionalized naphthalene derivatives, particularly the glycosyl 8-alkynyl-1-naphthoate donors. Herein, we report an efficient and scalable approach for the synthesis of a variety of 8-iodo-1-naphthoates via a modified photoinduced Suárez halodecarboxylation reaction. Derivatization of the 8-iodo-naphthoates enables access to a wide range of 1,8-difunctionalized naphthalene derivatives. In particular, Sonogashira coupling reactions using diverse alkynes clearly demonstrate the superior reactivity and functional group tolerance of 8-iodo-1-naphthoate compared to its bromide counterpart. This practical and cost-effective synthetic approach is expected to greatly facilitate the broader application of glycosyl 8-alkynyl-1-naphthoates in glycosylation chemistry.
{"title":"Scalable synthesis of 8-iodo-1-naphthoate via photoinduced Suárez halodecarboxylation for the preparation of glycosyl donors","authors":"Mei Chen (Investigation) , Bangxing Hao (Investigation) , Liran Yang (Investigation) , Feiyan Xie (Investigation) , Panpan Wang (Investigation) , Peifan Xu (Investigation) , Jingyang Wei (Investigation) , Jimin Xu (Investigation) , Yugen Zhu (Supervision Writing – original draft)","doi":"10.1080/07328303.2025.2552365","DOIUrl":"10.1080/07328303.2025.2552365","url":null,"abstract":"<div><div>8-Iodo-1-naphthoate is a key intermediate for the versatile preparation of 1,8-difunctionalized naphthalene derivatives, particularly the glycosyl 8-alkynyl-1-naphthoate donors. Herein, we report an efficient and scalable approach for the synthesis of a variety of 8-iodo-1-naphthoates via a modified photoinduced Suárez halodecarboxylation reaction. Derivatization of the 8-iodo-naphthoates enables access to a wide range of 1,8-difunctionalized naphthalene derivatives. In particular, Sonogashira coupling reactions using diverse alkynes clearly demonstrate the superior reactivity and functional group tolerance of 8-iodo-1-naphthoate compared to its bromide counterpart. This practical and cost-effective synthetic approach is expected to greatly facilitate the broader application of glycosyl 8-alkynyl-1-naphthoates in glycosylation chemistry.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"44 7","pages":"Pages 312-340"},"PeriodicalIF":2.2,"publicationDate":"2025-08-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145464854","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}
Pub Date : 2025-07-24DOI: 10.1080/07328303.2025.2527564
Ji-yu Chen , Ji-wen Sheng , Ting Wang , Yu-jie Yang , Jie Yang , Hong-wei Li , Han-tong Xiu , Xuan-chen Lu , Dong-mei Liu
A water-soluble polysaccharide (AFP) was extracted from Athyrium Multidentatum (Doll.) Ching by water extraction and alcohol precipitation method and purified by column chromatography. AFP was characterized by Fourier transform infrared (FT–IR) spectroscopy, ultraviolet-visible (UV–Vis) spectroscopy, circular dichroism (CD) spectroscopy, scanning electron microscopy (SEM), atomic force microscopy (AFM), Congo red (CR) binding assay, monosaccharide composition and molecular weight analyses. 1D and 2D nuclear magnetic resonance (NMR) studies revealed two structural components in AFP, which are →4-β-D-Manp-(1→4)-β-D-Xylp-(1→4)-β-D-Xylp-(1→2)-β-D-Galp-(1→ and β-D-Glcp-(1→4)-β-D-Glcp-(1→4)-β-D-Glcp-(1→2)-β-D-Galp-(1→. AFP exhibited significant immunological activities in both normal and immunosuppressed mice. Dectin-2/SYK/MAPK/non-classical NF-κB signaling pathways might play a crucial role in the immunomodulatory actions of AFP. Current results provided an important basis for the development of AFP as a natural immunoregulator.
从多齿胸草（Athyrium Multidentatum, Doll）中提取水溶性多糖（AFP）。经水提醇沉法纯化，柱层析法纯化。采用傅里叶变换红外（FT-IR）光谱、紫外-可见（UV-Vis）光谱、圆二色（CD）光谱、扫描电镜（SEM）、原子力显微镜（AFM）、刚果红（CR）结合实验、单糖组成和分子量分析对AFP进行了表征。1D和2D核磁共振（NMR）研究揭示了AFP的两种结构成分：→4-β- d - manp -(1→4)-β- d - xylp -(1→4)-β- d - xylp -(1→2)-β- d - galp -(1→4)-β-D-Glcp-(1→4)-β-D-Glcp-(1→2)-β- d - galp -(1→2)-β- d - galp -（1→）。AFP在正常小鼠和免疫抑制小鼠中均表现出显著的免疫活性。Dectin-2/SYK/MAPK/非经典NF-κB信号通路可能在AFP的免疫调节作用中发挥重要作用。目前的结果为AFP作为一种天然免疫调节剂的开发提供了重要的基础。
{"title":"Structural characterization, immune activity, and action mechanisms of fractionated polysaccharides from Athyrium multidentatum (Doll.) Ching","authors":"Ji-yu Chen , Ji-wen Sheng , Ting Wang , Yu-jie Yang , Jie Yang , Hong-wei Li , Han-tong Xiu , Xuan-chen Lu , Dong-mei Liu","doi":"10.1080/07328303.2025.2527564","DOIUrl":"10.1080/07328303.2025.2527564","url":null,"abstract":"<div><div>A water-soluble polysaccharide (AFP) was extracted from <em>Athyrium Multidentatum</em> (Doll.) Ching by water extraction and alcohol precipitation method and purified by column chromatography. AFP was characterized by Fourier transform infrared (FT–IR) spectroscopy, ultraviolet-visible (UV–Vis) spectroscopy, circular dichroism (CD) spectroscopy, scanning electron microscopy (SEM), atomic force microscopy (AFM), Congo red (CR) binding assay, monosaccharide composition and molecular weight analyses. 1D and 2D nuclear magnetic resonance (NMR) studies revealed two structural components in AFP, which are →4-β-D-Man<em>p</em>-(1→4)-β-D-Xyl<em>p</em>-(1→4)-β-D-Xyl<em>p</em>-(1→2)-β-D-Gal<em>p</em>-(1→ and β-D-Glc<em>p</em>-(1→4)-β-D-Glc<em>p</em>-(1→4)-β-D-Glc<em>p</em>-(1→2)-β-D-Gal<em>p</em>-(1→. AFP exhibited significant immunological activities in both normal and immunosuppressed mice. Dectin-2/SYK/MAPK/non-classical NF-κB signaling pathways might play a crucial role in the immunomodulatory actions of AFP. Current results provided an important basis for the development of AFP as a natural immunoregulator.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"44 4","pages":"Pages 196-230"},"PeriodicalIF":2.2,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145195919","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}
Pub Date : 2025-07-24DOI: 10.1080/07328303.2025.2488772
Rayssa de Cassia Alves Iemini , Dalila Junqueira Alvarenga , Ana Laura Marques Trinca , Guilherme Moreira Guidetti , Adriano Lucas da Luz Salgado , Isabela Darcie Pascoini , Jamie Anthony Hawkes , Diogo Teixeira Carvalho , Lucas Lopardi Franco
Glycosides have gained increasing significance due to their roles in energy provision, structural function, and intercellular communication in living organisms. This recognition laid the foundation for advancements in glycobiology and pharmacology. This review traces the evolution of sugar modification methodologies to aglycones throughout the 20th century, culminating in the development of a groundbreaking coupling approach utilizing triazoles as molecular linkers. The “Click Chemistry,” an innovation in [2 + 3] cycloaddition, has allowed for the formation of glyco-compounds through energetically favorable reactions, and usually requires prior preparation of the terminal alkyne precursor and organic azide. This strategy has the significant benefit as a “synthetic structural access tool” – providing a way to achieve structures with regioselectivity that would not be accessible via other methods. This coupling method has emerged as a powerful tool in modern glyco-chemistry, enabling the synthesis of novel compounds with significant therapeutic potential. The triazole linkage can improve the stability (dependent on the individual molecules) and bioactivity of glycosides but also opens new venues for the development of drug candidates with enhanced efficacy and broader applications in medicinal chemistry. This review highlights the importance of glycotriazoles in advancing the field of medicinal chemistry and their potentials in future therapeutic development.
{"title":"The importance of glycotriazoles in medicinal chemistry – A narrative review","authors":"Rayssa de Cassia Alves Iemini , Dalila Junqueira Alvarenga , Ana Laura Marques Trinca , Guilherme Moreira Guidetti , Adriano Lucas da Luz Salgado , Isabela Darcie Pascoini , Jamie Anthony Hawkes , Diogo Teixeira Carvalho , Lucas Lopardi Franco","doi":"10.1080/07328303.2025.2488772","DOIUrl":"10.1080/07328303.2025.2488772","url":null,"abstract":"<div><div>Glycosides have gained increasing significance due to their roles in energy provision, structural function, and intercellular communication in living organisms. This recognition laid the foundation for advancements in glycobiology and pharmacology. This review traces the evolution of sugar modification methodologies to aglycones throughout the 20th century, culminating in the development of a groundbreaking coupling approach utilizing triazoles as molecular linkers. The “Click Chemistry,” an innovation in [2 + 3] cycloaddition, has allowed for the formation of glyco-compounds through energetically favorable reactions, and usually requires prior preparation of the terminal alkyne precursor and organic azide. This strategy has the significant benefit as a “synthetic structural access tool” – providing a way to achieve structures with regioselectivity that would not be accessible via other methods. This coupling method has emerged as a powerful tool in modern glyco-chemistry, enabling the synthesis of novel compounds with significant therapeutic potential. The triazole linkage can improve the stability (dependent on the individual molecules) and bioactivity of glycosides but also opens new venues for the development of drug candidates with enhanced efficacy and broader applications in medicinal chemistry. This review highlights the importance of glycotriazoles in advancing the field of medicinal chemistry and their potentials in future therapeutic development.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"44 4","pages":"Pages 133-159"},"PeriodicalIF":2.2,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145195921","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}
Pub Date : 2025-07-24DOI: 10.1080/07328303.2025.2480564
Mohamed S. Amer , Khouloud M. Barakat , Hassan A. H. Ibrahim , Koichi Matsuo , Mohamed I. A. Ibrahim
Exopolysaccharides (EPSs) are sugar-based biopolymers produced by bacteria in response to environmental stress. Bacterial EPSs (BEPSs) have attracted attention across multiple industries due to their biodegradable and nontoxic nature. Their large-scale production and ease of purification make BEPSs more favorable than other intracellular and cell wall polysaccharides. Two key approaches are used to enhance BEPS yields: metabolic engineering and the utilization of low-cost materials for eco-friendly production. Despite ongoing efforts to isolate and classify new marine BEPSs, only a few have been industrially utilized. The discovery of BEPSs with novel sugar compositions or structural modifications could unlock new applications. Currently, marine BEPSs are used as thickeners, stabilizers, and gelling agents in the food industry and show potential in cosmetics, biotechnology, wastewater treatment, petroleum recovery, and textiles. While their use is still in the early stage, BEPSs hold significant promise as versatile biomaterials. This review highlights bacterial sources of marine EPSs and explores their industrial potential.
{"title":"An overview on marine bacterial exopolysaccharides and their industrial applications","authors":"Mohamed S. Amer , Khouloud M. Barakat , Hassan A. H. Ibrahim , Koichi Matsuo , Mohamed I. A. Ibrahim","doi":"10.1080/07328303.2025.2480564","DOIUrl":"10.1080/07328303.2025.2480564","url":null,"abstract":"<div><div>Exopolysaccharides (EPSs) are sugar-based biopolymers produced by bacteria in response to environmental stress. Bacterial EPSs (BEPSs) have attracted attention across multiple industries due to their biodegradable and nontoxic nature. Their large-scale production and ease of purification make BEPSs more favorable than other intracellular and cell wall polysaccharides. Two key approaches are used to enhance BEPS yields: metabolic engineering and the utilization of low-cost materials for eco-friendly production. Despite ongoing efforts to isolate and classify new marine BEPSs, only a few have been industrially utilized. The discovery of BEPSs with novel sugar compositions or structural modifications could unlock new applications. Currently, marine BEPSs are used as thickeners, stabilizers, and gelling agents in the food industry and show potential in cosmetics, biotechnology, wastewater treatment, petroleum recovery, and textiles. While their use is still in the early stage, BEPSs hold significant promise as versatile biomaterials. This review highlights bacterial sources of marine EPSs and explores their industrial potential.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"44 4","pages":"Pages 95-132"},"PeriodicalIF":2.2,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145195920","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}
Pub Date : 2025-07-24DOI: 10.1080/07328303.2025.2530053
Ananda S. Amarasekara , Uchechukwu G. Ariwodo , Harshica Fernando
Understanding intermolecular interactions between cellulose and metal salts, and in particularly with anions, is crucial in development of cellulose composites and processing methods. Intermolecular interactions between cellulose model compound D-cellobiose and 14 sodium salts were evaluated using Fourier-Transform Infrared (FT-IR) spectroscopy, thermogravimetric (TG), and computational analysis tools. In FT-IR, shifts in 10 distinct bands in the D-cellobiose spectra were monitored to evaluate interactions between D-cellobiose and sodium salts. Na2B4O3 and Na3PO4 caused the highest total shifts of 61.85 and 34.08 cm−1, respectively. Mixing with salt caused lowering the initial decomposition temperatures in 10 out of the 14 salts. In density functional theory (DFT) study, Na2B4O7 and D-cellobiose mixture showed negative binding energies of −11.18, −25.3, −30.9, and −12.2 kJ/mol in approaching α- and β-D-cellobiose from up and down faces. In addition, FT-IR data showed the strong interaction between borate anion and carbohydrate, where mixing Na2B4O7 with D-cellobiose resulted in the largest total shift of 61.85 cm−1 in the ten IR bands monitored. The strong interactions between Na2B4O7 and D-cellobiose were explained as a result of Lewis acidity of boron, as well as multiple B and O atoms present in the anion and strong hydrogen bonding and dipolar interactions between B and O atoms.
{"title":"Insight into interactions between cellulose model D-cellobiose and fourteen selected sodium salts using FT-IR, thermogravimetry, and computational analysis tools","authors":"Ananda S. Amarasekara , Uchechukwu G. Ariwodo , Harshica Fernando","doi":"10.1080/07328303.2025.2530053","DOIUrl":"10.1080/07328303.2025.2530053","url":null,"abstract":"<div><div>Understanding intermolecular interactions between cellulose and metal salts, and in particularly with anions, is crucial in development of cellulose composites and processing methods. Intermolecular interactions between cellulose model compound D-cellobiose and 14 sodium salts were evaluated using Fourier-Transform Infrared (FT-IR) spectroscopy, thermogravimetric (TG), and computational analysis tools. In FT-IR, shifts in 10 distinct bands in the D-cellobiose spectra were monitored to evaluate interactions between D-cellobiose and sodium salts. Na<sub>2</sub>B<sub>4</sub>O<sub>3</sub> and Na<sub>3</sub>PO<sub>4</sub> caused the highest total shifts of 61.85 and 34.08 cm<sup>−1</sup>, respectively. Mixing with salt caused lowering the initial decomposition temperatures in 10 out of the 14 salts. In density functional theory (DFT) study, Na<sub>2</sub>B<sub>4</sub>O<sub>7</sub> and D-cellobiose mixture showed negative binding energies of −11.18, −25.3, −30.9, and −12.2 kJ/mol in approaching α- and β-D-cellobiose from up and down faces. In addition, FT-IR data showed the strong interaction between borate anion and carbohydrate, where mixing Na<sub>2</sub>B<sub>4</sub>O<sub>7</sub> with D-cellobiose resulted in the largest total shift of 61.85 cm<sup>−1</sup> in the ten IR bands monitored. The strong interactions between Na<sub>2</sub>B<sub>4</sub>O<sub>7</sub> and D-cellobiose were explained as a result of Lewis acidity of boron, as well as multiple B and O atoms present in the anion and strong hydrogen bonding and dipolar interactions between B and O atoms.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"44 4","pages":"Pages 179-195"},"PeriodicalIF":2.2,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145195887","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}
We report a convenient and highly efficient protocol for the acetonation of free sugars, enabling cis-O-isopropylidene saccharide derivatives under ultrasonic irradiation at ambient temperature. Triflic acid (TfOH) in acetone is identified as a mild and effective reagent for the chemoselective O-isopropylidenation of polyhydroxy compounds comprising aldo/keto-hexoses or aldo-pentoses. The synthetic utility of this approach was demonstrated through the preparation of various O-isopropylidene-protected sugar derivatives, which serve as key chiral intermediates for assembling important carbohydrate scaffolds and glycoconjugates. The use of ultrasonic irradiation as an environmentally benign energy source highlights the potential for this method to make a significant contribution to synthetic organic chemistry.
我们报道了一种方便和高效的游离糖丙酮化方法，使顺- o -异丙基糖衍生物在室温下的超声照射下成为可能。丙酮中的三羧酸（TfOH）是一种温和而有效的化学选择性o-异丙基化试剂，用于多羟基化合物的化学选择性o-异丙基化，包括醛酮己糖或醛戊糖。通过制备各种o -异丙烯保护的糖衍生物，证明了该方法的合成实用性，这些糖衍生物是组装重要碳水化合物支架和糖缀合物的关键手性中间体。超声波辐射作为一种环境友好的能源，突出了这种方法对合成有机化学做出重大贡献的潜力。
{"title":"Chemoselective acetonation and one-pot glycosylation/acetylation of free sugars under ultrasonic green energy source","authors":"Nitin Kumar , Ankit Yadav , Saurabh Saini , Sudhir Kashyap","doi":"10.1080/07328303.2025.2527571","DOIUrl":"10.1080/07328303.2025.2527571","url":null,"abstract":"<div><div>We report a convenient and highly efficient protocol for the acetonation of free sugars, enabling <em>cis-O-</em>isopropylidene saccharide derivatives under ultrasonic irradiation at ambient temperature. Triflic acid (TfOH) in acetone is identified as a mild and effective reagent for the chemoselective <em>O</em>-isopropylidenation of polyhydroxy compounds comprising aldo/keto-hexoses or aldo-pentoses. The synthetic utility of this approach was demonstrated through the preparation of various <em>O</em>-isopropylidene-protected sugar derivatives, which serve as key chiral intermediates for assembling important carbohydrate scaffolds and glycoconjugates. The use of ultrasonic irradiation as an environmentally benign energy source highlights the potential for this method to make a significant contribution to synthetic organic chemistry.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"44 4","pages":"Pages 160-178"},"PeriodicalIF":2.2,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145195886","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}
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