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Biopolymeric starch-based matrix: A sustainable platform for slow release fertilizers
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-03-28 DOI: 10.1016/j.carres.2025.109474
Mani Prabha , Puneet Tiwari , Pankaj Kumar Yadav , Vandana Singh , Devendra Narayan Tripathi , Tulika Malviya
{"title":"Biopolymeric starch-based matrix: A sustainable platform for slow release fertilizers","authors":"Mani Prabha ,&nbsp;Puneet Tiwari ,&nbsp;Pankaj Kumar Yadav ,&nbsp;Vandana Singh ,&nbsp;Devendra Narayan Tripathi ,&nbsp;Tulika Malviya","doi":"10.1016/j.carres.2025.109474","DOIUrl":"10.1016/j.carres.2025.109474","url":null,"abstract":"<div><div>Starch, a renewable and biodegradable biopolymer, offers immense potential as a base material for developing slow-release fertilizers. This study focuses on utilizing starch-based materials to encapsulate nutrients that enable slow and regulated release in response to environmental conditions. Various methods like chemical reduction, crosslinking, sol-gel, mixing and blending, etc. with other polymers were explored for modification of starch. These alterations may help to increase the mechanical strength and also enhance the water resistance along with the release dynamics of the fertilizer matrix. The potential use of starch-based fertilizers in maximizing crop yield as well as plant growth and lowering nutrient losses was also explored. This article offers a comprehensive overview of the most recent findings on starch, including its modification in addition to its applications in slow-release fertilizers. It also highlights their ability to boost productivity, enhance nutrient management, and support sustainable farming practices.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109474"},"PeriodicalIF":2.4,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143760832","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
Edible films based on sulfated polysaccharides from the seaweed Gracilaria birdiae: Physicochemical, optical and mechanical properties
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-03-28 DOI: 10.1016/j.carres.2025.109473
Cláudia Brandão Vieira , Juliana Rabelo Sousa , Diego Alves Do Vale , Cybele Pinheiro Guimarães , Karolina Costa de Sousa , Adriano Lincoln Albuquerque Mattos , André Luís Coelho Silva , Men de Sá Moreira Souza Filho , Bartolomeu Warlene Silva Souza
{"title":"Edible films based on sulfated polysaccharides from the seaweed Gracilaria birdiae: Physicochemical, optical and mechanical properties","authors":"Cláudia Brandão Vieira ,&nbsp;Juliana Rabelo Sousa ,&nbsp;Diego Alves Do Vale ,&nbsp;Cybele Pinheiro Guimarães ,&nbsp;Karolina Costa de Sousa ,&nbsp;Adriano Lincoln Albuquerque Mattos ,&nbsp;André Luís Coelho Silva ,&nbsp;Men de Sá Moreira Souza Filho ,&nbsp;Bartolomeu Warlene Silva Souza","doi":"10.1016/j.carres.2025.109473","DOIUrl":"10.1016/j.carres.2025.109473","url":null,"abstract":"<div><div>Sulfated polysaccharide (SP) was successfully extracted from rhodophyta <em>Gracilaria birdiae</em> cultivated in northeast Brazil. For the first time, edible SP films from G. birdiae were formulated by the casting method using an experimental design 3<sup>2</sup>, in which the variables were SP concentration and glycerol concentration. A polysaccharide extraction yield of 26.4 % was obtained through hot aqueous extraction and purification by dialysis. The chemical composition indicated the quality of the SP due to the high total carbohydrate (85.1 %) and sulfate (8.1 %) contents and the absence of proteins. Structural characterization showed the presence, besides the sulfate group, of the methylated monosaccharide residues, namely 3,6-α-<span>l</span>-anhydrogalactose-2-O-methyl and β-<span>d</span>-galactose-6-O-methyl with methylation degree of 0.257. In addition, the polysaccharide chain was mainly composed of 3,6-α-<span>l</span>-anhydrogalactose → β-<span>d</span>-galactose, α-<span>l</span>-galactose-6-sulfate → β-<span>d</span>-galactose, β-<span>d</span>-galactose → 3,6-α-<span>l</span>-anhydrogalactose, and β-<span>d</span>-galactose → α-<span>l</span>-galactose-6-sulfato. SP was also considered thermostable, showing a thermal degradation pattern similar to that of galactans. Through experimental design, it was observed that the film formulation with 2 % SP and 0.2 % glycerol presented the best mechanical, physico-chemical and optical properties for application in food packaging.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109473"},"PeriodicalIF":2.4,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143748014","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
Construction of 1,6-anhydro-functionalized carbohydrate-fused spiro-chromanones via intramolecular domino/spirocyclization
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-03-28 DOI: 10.1016/j.carres.2025.109466
Nicole Jankowski , Christopher Hager , Holly Arcure , Jessie Lopez , Any M. Barrios Gomez , Zbigniew J. Witczak , Roman Bielski , Donald E. Mencer
{"title":"Construction of 1,6-anhydro-functionalized carbohydrate-fused spiro-chromanones via intramolecular domino/spirocyclization","authors":"Nicole Jankowski ,&nbsp;Christopher Hager ,&nbsp;Holly Arcure ,&nbsp;Jessie Lopez ,&nbsp;Any M. Barrios Gomez ,&nbsp;Zbigniew J. Witczak ,&nbsp;Roman Bielski ,&nbsp;Donald E. Mencer","doi":"10.1016/j.carres.2025.109466","DOIUrl":"10.1016/j.carres.2025.109466","url":null,"abstract":"<div><div>The synthetic protocol for the first synthesis of carbohydrate-fused <em>spiro</em>-chromanones <em>via</em> intramolecular domino reaction between <em>o</em>-hydroxyacetophenones and dihydrolevoglucosenone (DHL) is described. The reactions proceed <em>via</em> the formation of an acetophenone (APh) enamine intermediate when performed in the presence of pyrrolidine in ethanol. The formation of a new carbon-carbon bond between nucleophilic carbon of the enamine of APh and C-2 of DHL is followed by cyclization, producing a new six-membered ring, as the result of an intramolecular domino process. Several substituted <em>o</em>-hydroxyacetophenones were reacted. The structure of products was determined using <sup>1</sup>H and <sup>13</sup>C NMR, GC-MS and X-ray crystallography. The yields are good to excellent (62–92 %), and the products are crystalline and easy to isolate. So far, the synthesized compounds were tested only for their antifungal properties. The results were disappointing.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109466"},"PeriodicalIF":2.4,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143760831","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
Complete assignment of 1H and 13C NMR signals of monoglucosylated high-mannose type glycan attached to asparagine
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-03-26 DOI: 10.1016/j.carres.2025.109468
Ryohei Uematsu , Izumi Sakamoto , Noriyoshi Manabe , Yoshiki Yamaguchi
{"title":"Complete assignment of 1H and 13C NMR signals of monoglucosylated high-mannose type glycan attached to asparagine","authors":"Ryohei Uematsu ,&nbsp;Izumi Sakamoto ,&nbsp;Noriyoshi Manabe ,&nbsp;Yoshiki Yamaguchi","doi":"10.1016/j.carres.2025.109468","DOIUrl":"10.1016/j.carres.2025.109468","url":null,"abstract":"<div><div>Glc<sub>1</sub>Man<sub>9</sub>GlcNAc<sub>2</sub> (G1M9) glycan and other high mannose-type glycans play key roles in the quality control mechanisms of glycoprotein synthesis. The lectin-like proteins calnexin (CNX) and calreticulin (CRT) specifically recognize G1M9 glycan and assist newly synthesized glycoproteins to achieving correct folding. Nuclear magnetic resonance (NMR) spectroscopy is a unique method for analyzing the conformation, dynamics and interactions of glycans like G1M9 glycan and CNX/CRT. Accurate assignment of <sup>1</sup>H and <sup>13</sup>C signals is a prerequisite for such analyses. Here, we present the complete assignment of <sup>1</sup>H and <sup>13</sup>C signals for the Asn-linked G1M9 glycan, modified at its N-terminus with a 9-fluorenylmethyloxycarbonyl (Fmoc) group (Fmoc-Asn-G1M9). Using conventional two-dimensional NMR techniques including <sup>1</sup>H–<sup>1</sup>H COSY, <sup>1</sup>H–<sup>1</sup>H NOESY, <sup>1</sup>H–<sup>13</sup>C HSQC, <sup>1</sup>H–<sup>13</sup>C HMBC and <sup>1</sup>H–<sup>13</sup>C HSQC-TOCSY, we achieved a comprehensive spectral assignment. Our results are consistent with previously reported assignments of the partial pentasaccharide structure of G1M9 glycan. This complete assessment of G1M9 glycan signals provides a foundation for detailed studies of its interactions with CNX/CRT, which will advance our understanding of the molecular mechanisms underlying glycoprotein quality control.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109468"},"PeriodicalIF":2.4,"publicationDate":"2025-03-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143738727","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
Chemical structure and anti-inflammatory effects on intestinal epithelial cells of a novel mannogalactan purified from Typhonium giganteum Engl.
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-03-26 DOI: 10.1016/j.carres.2025.109467
Hongchen Luo , Zhengyang Lai , Lexue Shi , Yulong Hu , Can Jin , Kan Ding
{"title":"Chemical structure and anti-inflammatory effects on intestinal epithelial cells of a novel mannogalactan purified from Typhonium giganteum Engl.","authors":"Hongchen Luo ,&nbsp;Zhengyang Lai ,&nbsp;Lexue Shi ,&nbsp;Yulong Hu ,&nbsp;Can Jin ,&nbsp;Kan Ding","doi":"10.1016/j.carres.2025.109467","DOIUrl":"10.1016/j.carres.2025.109467","url":null,"abstract":"<div><div>Inflammatory bowel disease (IBD) remains a pressing global health challenge due to its complex pathogenesis and limited treatment efficacy. Mannogalactans, abundant in certain algae and edible fungi, are recognized for their diverse biological functions, particularly their potent anti-inflammatory effects. Motivated by these findings, we hypothesized that <em>Typhonium giganteum</em> Engl. may contain structurally analogous mannogalactans with therapeutic potential against enteritis. To investigate, we isolated and purified a homogeneous polysaccharide, BFZ213, using hot water extraction, ethanol precipitation, and chromatographic techniques. Comprehensive structural analysis, employing methylation analysis, partial acid hydrolysis, 1-phenyl-3-methyl-5-pyrazolone (PMP) derivatization, infrared spectroscopy, HPLC, GC-MS, and NMR spectroscopy, identified BFZ213 as a novel mannogalactan (160 kDa). The backbone comprises 1, 3-linked mannose, 1, 2, 3-linked mannose, 1, 4-linked glucuronic acid, and 1, 2, 4, 6-linked galactose, with branching at the C-4 and C-6 positions of 1, 2, 4, 6-linked galactose, including 1, 4-linked galactose, 1, 6-linked galactose, terminal galactose, and arabinose. Bioactivity studies demonstrated that BFZ213 significantly suppressed TNF-α and IL-1β secretion in LPS-stimulated NCM460 cells and attenuated MAPK and NF-κB signaling by inhibiting the phosphorylation of p38, JNK, p65, and IκBα. These results highlight BFZ213 as a promising lead compound for IBD therapy, underscoring the therapeutic relevance of mannogalactans.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109467"},"PeriodicalIF":2.4,"publicationDate":"2025-03-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143734864","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
Structure, rheology and antioxidant properties of a polysaccharide from Atractylodes macrocephala in Pan'an
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-03-21 DOI: 10.1016/j.carres.2025.109464
Min Lin , Guodong Wang , Yunzhi Li
{"title":"Structure, rheology and antioxidant properties of a polysaccharide from Atractylodes macrocephala in Pan'an","authors":"Min Lin ,&nbsp;Guodong Wang ,&nbsp;Yunzhi Li","doi":"10.1016/j.carres.2025.109464","DOIUrl":"10.1016/j.carres.2025.109464","url":null,"abstract":"<div><div>To date, no studies have reported on the structure and properties of the polysaccharides from <em>Atractylodes macrocephala</em> cultivated in Pan'an. In this paper, a polysaccharide designated as RAMP1 was isolated from <em>A. macrocephala</em> in Pan'an for the first time. Its structure was determined as a heteropolysaccharide consisting of fructose and glucose in a molar ratio of 20:1, with a molecular weight of 3494 Da based on chemical and NMR analysis. Scanning electron microscopy analysis revealed that RAMP1 presented a smooth flake structure with irregular curls. Thermal analysis results indicated that RAMP1 had high thermal stability below 165 °C. Rheological studies indicated that both temperature and concentration affected the viscosity of RAMP1. The viscosity of the RAMP1 solution decreased as the shear rate increased, displaying shear - thinning behavior, suggesting that the RAMP1 solution was a non - Newtonian fluid. RAMP1 showed potent dose - dependent antioxidant activity against DPPH, superoxide, ABTS, and hydroxyl radicals, with the strongest inhibition against hydroxyl radicals (83.97 ± 1.62 % at 8 mg/mL). This paper reports for the first time on the structure, rheology, and antioxidant properties of the polysaccharide (RAMP1) from <em>A. macrocephala</em> in Pan'an. These results highlight the potential applications of RAMP1 in the food and biotechnology industries.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109464"},"PeriodicalIF":2.4,"publicationDate":"2025-03-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143705423","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
Effects of 6-O-α-maltosyl-γ cyclodextrin on proliferation and cellular uptake in mouse mastocytoma P-815 cells
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-03-19 DOI: 10.1016/j.carres.2025.109463
Yasuyo Okada , Naomi Inoue , Ai Sanagi , Atsushi Ichikawa
{"title":"Effects of 6-O-α-maltosyl-γ cyclodextrin on proliferation and cellular uptake in mouse mastocytoma P-815 cells","authors":"Yasuyo Okada ,&nbsp;Naomi Inoue ,&nbsp;Ai Sanagi ,&nbsp;Atsushi Ichikawa","doi":"10.1016/j.carres.2025.109463","DOIUrl":"10.1016/j.carres.2025.109463","url":null,"abstract":"<div><div>6-<em>O</em>-α-Maltosyl-γ cyclodextrin (Mal-γCD) is a branched γCD with α(1 → 6) branched maltose on the γCD ring. Mal-γCD is more water-soluble and safer than the parent γCD, has the same ability to form inclusion complexes, and the formed inclusion complexes are highly water-soluble. There is limited information regarding Mal-γCD both in vitro and in vivo, and the effects of Mal-γCD on proliferation, uptake, metabolism, and the cell cycle of target cells remain unknown. In this study, we investigated the effects of Mal-γCD on the proliferation of mastocytoma P-815 cells (P-815 cells) focusing on its impact on the cellular uptake, endocytosis, metabolism, and the cell cycle. We found that Mal-γCD, but not the parent γCD, inhibited the proliferation of P-815 cells in a time- and concentration-dependent manner, although the inhibition was reversible. Mal-γCD caused an increase in the number of cells in the G1 and G2 phases and a decrease in the number of cells in the S phase. Mal-γCD was taken up by P-815 cells and metabolized to 6-<em>O</em>-α-<span>d</span>-glucosyl-γCD and glucose by cellular α-glucosidases in a time-dependent manner. Its uptake was enhanced in S-phase-synchronized P-815 cells, was temperature- and energy-dependent, and was suppressed by general endocytosis inhibitors such as cytochalasin D and colchicine, as well as by Na<sup>+</sup>/K<sup>+</sup>-ATPase inhibitors such as digoxin, quinidine, and verapamil. These findings demonstrate that Mal-γCD exerts a growth inhibitory effect on proliferative cells by delaying the cell cycle at the G1/S and G2/M transition phases, which may be closely associated with endocytosis.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109463"},"PeriodicalIF":2.4,"publicationDate":"2025-03-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143679013","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
Photo-induced glycosylation using edible polyphenol ellagic acid
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-03-17 DOI: 10.1016/j.carres.2025.109461
Hidenari Shigeta, Satomi Goi, Daisuke Takahashi, Kazunobu Toshima
{"title":"Photo-induced glycosylation using edible polyphenol ellagic acid","authors":"Hidenari Shigeta,&nbsp;Satomi Goi,&nbsp;Daisuke Takahashi,&nbsp;Kazunobu Toshima","doi":"10.1016/j.carres.2025.109461","DOIUrl":"10.1016/j.carres.2025.109461","url":null,"abstract":"<div><div>Photo-induced glycosylation reactions of trichloroacetoimidate donors with alcohol acceptors were investigated under visible light (470 nm) irradiation using the edible polyphenol, ellagic acid. We found, for the first time, that these glycosylations proceeded smoothly under mild reaction conditions, and the corresponding glycosides were obtained in high yields. Furthermore, this glycosylation method was applicable to a wide range of trichloroacetimidate donors and alcohol acceptors, and showed high chemoselectivity over glycosyl phosphate, fluoride, glycal, thioglycoside, and (<em>N</em>-phenyl)trifluoroacetimidate.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109461"},"PeriodicalIF":2.4,"publicationDate":"2025-03-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143678964","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 studies on the O-polysaccharide of Vreelandella alkaliphila strain B521
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-03-15 DOI: 10.1016/j.carres.2025.109462
Elena N. Sigida , Maxim S. Kokoulin , Vlada S. Belova , Marina S. Kuzina , Natalya S. Velichko , Vyacheslav S. Grinev , Yuliya P. Fedonenko
{"title":"Structural studies on the O-polysaccharide of Vreelandella alkaliphila strain B521","authors":"Elena N. Sigida ,&nbsp;Maxim S. Kokoulin ,&nbsp;Vlada S. Belova ,&nbsp;Marina S. Kuzina ,&nbsp;Natalya S. Velichko ,&nbsp;Vyacheslav S. Grinev ,&nbsp;Yuliya P. Fedonenko","doi":"10.1016/j.carres.2025.109462","DOIUrl":"10.1016/j.carres.2025.109462","url":null,"abstract":"<div><div>Lipopolysaccharide was obtained by hot aqueous-phenol extraction from <em>Vreelandella alkaliphila</em> B521, a moderately halophilic gram-negative bacterium isolated from mud of Lake Botkul, Volgograd Region, Russia. The O-polysaccharide (OPS) was released by mild acid hydrolysis of the lipopolysaccharide and was structurally characterized by chemical analyses and by 1D and 2D NMR spectroscopy. The following structure of the OPS trisaccharide repeating unit was identified: →4)-α-<span>l</span>-Gul<em>p</em>NAcA-(1 → 4)-α-<span>l</span>-Gul<em>p</em>NAcA-(1 → 6)-α-<span>d</span>-Glc<em>p</em>NAc-(1→</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109462"},"PeriodicalIF":2.4,"publicationDate":"2025-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143644438","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
Ganglioside analog synthesis via late-stage sialylation and fatty acid introduction
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-03-15 DOI: 10.1016/j.carres.2025.109460
Maina Takahashi , Naoko Komura , Hide-Nori Tanaka , Akihiro Imamura , Hideharu Ishida , Hiromune Ando
{"title":"Ganglioside analog synthesis via late-stage sialylation and fatty acid introduction","authors":"Maina Takahashi ,&nbsp;Naoko Komura ,&nbsp;Hide-Nori Tanaka ,&nbsp;Akihiro Imamura ,&nbsp;Hideharu Ishida ,&nbsp;Hiromune Ando","doi":"10.1016/j.carres.2025.109460","DOIUrl":"10.1016/j.carres.2025.109460","url":null,"abstract":"<div><div>Gangliosides are sialylated glycosphingolipids comprising various chemical forms of glycans and ceramides. They perform various biological functions in cell plasma membranes. Differences in the sialic acid forms (Neu5Ac and Neu5Gc) and ceramide species (lengths and degrees of unsaturation) result in variations in ganglioside's functions, even though their core glycan structures are common. However, ganglioside research requires considerable effort due to complications in their chemical synthesis. Further, a facile supply of ganglioside samples with variations in substructures is required for comprehensive research. We recently reported a chemical synthesis method for gangliosides <em>via</em> the late-stage sialylation of oligosaccharyl ceramide acceptors. Based on this method, we developed a synthetic method <em>via</em> late-stage incorporation of sialic acids and fatty acids. An oligosaccharyl sphingosine acceptor was efficiently sialylated using a minimally protected design to enhance the reactivity of the acceptor hydroxyl group. Subsequently, the azide group at the sphingosine C2 position was reduced for fatty acid incorporation. Further several steps of Neu C5-modification (<em>N</em>-Ac or <em>N</em>-Gc), global deprotection, and fluorescent dye incorporation enabled neolacto-series ganglioside (sialyl-neolactotetraosylceramide, Neu nLc<sub>4</sub>Cer) probe synthesis. These results indicate the applicability of this method for the systematic synthesis of ganglioside analogs with modifications to the sialic acid or lipid structure.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109460"},"PeriodicalIF":2.4,"publicationDate":"2025-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143679014","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
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