Carbohydrate Research最新文献

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Plant-based biodegradable and biocompatible polymers for tissue engineering applications 用于组织工程应用的植物基可生物降解和生物相容性聚合物。
IF 2.5 3区 化学
Carbohydrate Research Pub Date : 2025-10-06 DOI: 10.1016/j.carres.2025.109699
Aditya Teja Guduru, Subramanian Sankaranarayanan, Dhiraj Bhatia
{"title":"Plant-based biodegradable and biocompatible polymers for tissue engineering applications","authors":"Aditya Teja Guduru,&nbsp;Subramanian Sankaranarayanan,&nbsp;Dhiraj Bhatia","doi":"10.1016/j.carres.2025.109699","DOIUrl":"10.1016/j.carres.2025.109699","url":null,"abstract":"<div><div>Tissue engineering has emerged as a potential area in regenerative medicine, leveraging biodegradable and biocompatible polymers to fabricate scaffolds for cell growth and tissue regeneration. Among biomaterials, plant-based polymers have garnered significant attention due to their sustainability, biocompatibility, and suitable mechanical properties. This review emphasises the innovative modifications in natural polymers such as fungal chitosan, nanocellulose composites, and hybrid plant-synthetic scaffolds-that address longstanding challenges in mechanical stability, degradation control, and bioactivity. By systematically comparing polysaccharides (e.g., cellulose, alginate) and proteins (soy, zein) across bone, cartilage, and wound healing applications, we identify structure-function relationships that enable tailored scaffold design. Finally, this review critically evaluates recent advances in plant-based polymers for tissue engineering, highlighting innovative modifications and unresolved challenges providing actionable strategies to advance plant derived biomaterials towards clinical transition.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"558 ","pages":"Article 109699"},"PeriodicalIF":2.5,"publicationDate":"2025-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145291210","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
A simplified NMR-based method to assign the absolute configuration of aldose monosaccharides 一种简化的基于核磁共振的醛糖单糖绝对构型分配方法。
IF 2.5 3区 化学
Carbohydrate Research Pub Date : 2025-10-06 DOI: 10.1016/j.carres.2025.109696
Neil P.J. Price , Karl E. Vermillion , Michael A. Jackson
{"title":"A simplified NMR-based method to assign the absolute configuration of aldose monosaccharides","authors":"Neil P.J. Price ,&nbsp;Karl E. Vermillion ,&nbsp;Michael A. Jackson","doi":"10.1016/j.carres.2025.109696","DOIUrl":"10.1016/j.carres.2025.109696","url":null,"abstract":"<div><div>A straightforward, aqueous-based procedure is described to determine the absolute configuration of aldose monosaccharides, a critical task in carbohydrate analysis. This approach leverages the reaction of aldose monosaccharide enantiomers with L-cysteine, a readily-available chiral amino acid, to form cyclic thiazolidine diastereomers. These derivatives can be analyzed using Heteronuclear Single Quantum Coherence (HSQC) NMR spectroscopy, specifically looking at the H-1 – C-1 proton-carbon single bond correlations. This NMR technique provides the necessary data to determine the absolute configuration of the parent monosaccharide. Several monosaccharide D-/L-enantiomeric pairs are analyzed as examples, and the technique is utilized to determine the compositional stereochemistry of complex polysaccharides (gellan and xanthan gums). We have also established the previously unknown stereochemistry of the arabinosyl residues found in frost grape polysaccharide (FGP) isolated from vines of the grape species, <em>Vitis riparia</em> Michx. The generalized method described is anticipated to be valuable to analytical carbohydrate chemists for the facile assignment of carbohydrate stereochemistry.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"558 ","pages":"Article 109696"},"PeriodicalIF":2.5,"publicationDate":"2025-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145312488","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
Autoclave extraction applied to residual mushroom biomass: An efficient method for high-yield polysaccharide recovery 高压灭菌法提取残蘑菇生物量:一种高效提取多糖的方法。
IF 2.5 3区 化学
Carbohydrate Research Pub Date : 2025-10-06 DOI: 10.1016/j.carres.2025.109698
Matheus Zavadinack , Hellen Abreu , Dib Mady Diniz Gomes , Shayane da Silva Milhorini , Fhernanda Ribeiro Smiderle , Lucimara M.C. Cordeiro , Marcello Iacomini
{"title":"Autoclave extraction applied to residual mushroom biomass: An efficient method for high-yield polysaccharide recovery","authors":"Matheus Zavadinack ,&nbsp;Hellen Abreu ,&nbsp;Dib Mady Diniz Gomes ,&nbsp;Shayane da Silva Milhorini ,&nbsp;Fhernanda Ribeiro Smiderle ,&nbsp;Lucimara M.C. Cordeiro ,&nbsp;Marcello Iacomini","doi":"10.1016/j.carres.2025.109698","DOIUrl":"10.1016/j.carres.2025.109698","url":null,"abstract":"<div><div>Mushroom-derived polysaccharides, particularly β-D-glucans, are valued for their biological activities and broad biotechnological applications. Although several conventional extraction methods have been established (cold-water, hot-water, and alkaline), the biomass that remains after exhaustive treatments is often discarded, despite its potential to retain valuable compounds. In this study, we evaluated whether residual laboratory materials from <em>Pleurotus pulmonarius</em>, <em>Pholiota nameko</em>, and <em>Amanita muscaria</em> still contain extractable polysaccharides by applying sequential autoclave extractions under aqueous, 5 % KOH, and 20 % KOH conditions. The extracts were precipitated with ethanol, quantified, and characterized by NMR, GC-MS, HPSEC-RI, and by total sugar and protein determinations<strong>.</strong> Significant yields were obtained, particularly with 5 % KOH, which produced up to 31.1 % in a single step, albeit with considerable protein content. Across extraction steps, a progressive decrease in molecular weight was observed, and monosaccharide analysis revealed that the extracts were composed predominantly of glucose. Structural characterization confirmed a predominance of β-D-glucans with (1→3)- and (1→6)-linkages, together with α-D-glucans with (1→3)- and (1→4)-linkages, as well as galactans and mannans. Overall, these findings demonstrate that autoclave extraction is a simple, efficient, and scalable approach to recover structurally diverse polysaccharides from mushroom residues, thereby enhancing resource utilization and opening new opportunities for fungal biomass valorization.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"558 ","pages":"Article 109698"},"PeriodicalIF":2.5,"publicationDate":"2025-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145291218","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
Ionic gelation based synthesis of chitosan nanoparticles from the waste shells of anomuran crab Albunea symmysta (Linnaeus, 1758) exhibits potential applications 以异源蟹(Linnaeus, 1758)废壳为原料,离子胶凝法制备壳聚糖纳米颗粒,具有潜在的应用前景。
IF 2.5 3区 化学
Carbohydrate Research Pub Date : 2025-10-04 DOI: 10.1016/j.carres.2025.109697
Francis Abisha Adline , Jinna Dowlath Nisa , Rangasamy Shanthi , Mullaivanam Ramasamy Sivakumar
{"title":"Ionic gelation based synthesis of chitosan nanoparticles from the waste shells of anomuran crab Albunea symmysta (Linnaeus, 1758) exhibits potential applications","authors":"Francis Abisha Adline ,&nbsp;Jinna Dowlath Nisa ,&nbsp;Rangasamy Shanthi ,&nbsp;Mullaivanam Ramasamy Sivakumar","doi":"10.1016/j.carres.2025.109697","DOIUrl":"10.1016/j.carres.2025.109697","url":null,"abstract":"<div><div>Seafood waste especially crustacean shells are often discarded at sea or landfilled. Therefore, the extraction of valuable biomolecules such as chitin and the synthesis of chitosan and its nanoparticles are considered a beneficial solution to reduce crustacean shell waste. In the present study, chitosan (ACs) was extracted from the shells of anomuran crab <em>Albunea symmysta</em> and chitosan nanoparticles (CsNP) were synthesized using the ionic gelation method. The degree of deacetylation of chitosan was found to be 82.85 %. FTIR analysis of ACs and CsNP depicted similar functional groups at corresponding peaks compared to commercial chitosan (CCs). XRD analysis confirmed the semi crystalline nature of CCs, ACs, while CsNP exhibited reduced crystallinity and more amorphous structure. DLS studies evidenced that the mean diameter of CsNP was 144.3 ± 11.8 nm and the zeta potential of both ACs and CsNP was found to be positive. SEM imaging of ACs exhibited rough, porous surface morphology whereas the CsNP exhibited smooth, spherical granular nanostructures. Elemental analysis via EDX confirmed the presence of key elements such as carbon (C), oxygen (O) and nitrogen (N) in both ACs and CsNP. TGA studies further demonstrated the thermal stability of CCs, ACs and CsNP. Moreover, CsNP exhibited significant antibacterial and anticoagulant activity and were effective in extending the shelf life of fruits through surface coating. Overall, the synthesis of ACs and CsNP presents a sustainable approach to crustacean shell waste utilization. These findings underscore the potential applications of CsNP in biomedical and food preservation fields.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"558 ","pages":"Article 109697"},"PeriodicalIF":2.5,"publicationDate":"2025-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145243785","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 characterization, in vitro antioxidant and lipid-lowering activities of purified polysaccharides from hawthorn leaf 山楂叶纯化多糖的结构表征、体外抗氧化和降脂活性。
IF 2.5 3区 化学
Carbohydrate Research Pub Date : 2025-10-03 DOI: 10.1016/j.carres.2025.109695
Ting Yang , Yang Yang , Rong Chen , Pinyi Gao , Danqi Li , Xuegui Liu
{"title":"Structural characterization, in vitro antioxidant and lipid-lowering activities of purified polysaccharides from hawthorn leaf","authors":"Ting Yang ,&nbsp;Yang Yang ,&nbsp;Rong Chen ,&nbsp;Pinyi Gao ,&nbsp;Danqi Li ,&nbsp;Xuegui Liu","doi":"10.1016/j.carres.2025.109695","DOIUrl":"10.1016/j.carres.2025.109695","url":null,"abstract":"<div><div>This study investigates the structural features and lipid-regulating mechanisms of hawthorn leaf polysaccharides (HLPs). Three acidic polysaccharides (HLP-1, HLP-2, and HLP-3) were isolated from hawthorn leaves and characterized via high-performance gel permeation chromatography (HPGPC), ion chromatography (IC), methylation analysis, and nuclear magnetic resonance (NMR) spectroscopy. Structural analyses revealed their molecular weights were 10.19 kDa, 400.38 kDa, and 435.52 kDa, respectively, with primary composition of galacturonic acid, galactose, and rhamnose. The Congo red assay indicated potential ordered aggregation with molecular weight-dependent thermal stability. Among the three, HLP-1 demonstrated the most potent <em>in vitro</em> bioactivity, including superior antioxidant capacity; in HepG2 cells, it most effectively reduced TG, TC, and LDL-c levels and increased HDL-c, outperforming HLP-2 and HLP-3. Mechanistically, HLP-1's hypolipidemic effect was linked to suppression of the <em>SREBP-1c</em> pathway. Furthermore, this study establishes the structure-activity relationship between HLPs' structural properties and lipid-lowering effects, laying a foundation for future HLP-based therapeutic interventions in metabolic diseases.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"558 ","pages":"Article 109695"},"PeriodicalIF":2.5,"publicationDate":"2025-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145238056","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
New partially silylated cyclodextrins with complex hydrogen bond networks 具有复杂氢键网络的部分硅基化环糊精
IF 2.5 3区 化学
Carbohydrate Research Pub Date : 2025-10-03 DOI: 10.1016/j.carres.2025.109692
Florent Pelus, Mikael Bols
{"title":"New partially silylated cyclodextrins with complex hydrogen bond networks","authors":"Florent Pelus,&nbsp;Mikael Bols","doi":"10.1016/j.carres.2025.109692","DOIUrl":"10.1016/j.carres.2025.109692","url":null,"abstract":"<div><div>A series of partially silylated and unsymmetrical α-, β- and γ-cyclodextrins were prepared and the NMR spectra in CDCl<sub>3</sub> were analyzed. All unsymmetrical compounds showed a complex pattern of OH signals similarly to what has previously been seen for 6<sup>A−F</sup>,2<sup>A</sup>-hepta-<em>O</em>-tertbutyldimethylsilyl α-cyclodextrin. The compounds ability to form hydrogen bond network is discussed.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"558 ","pages":"Article 109692"},"PeriodicalIF":2.5,"publicationDate":"2025-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145217001","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
Crystallisation of 2,3,4-tri-O-acetyl-α-d- and α-l-xylopyranosyl bromides in enantiomorphic space groups 2,3,4-三- o -乙酰-α-d-和α-l-木吡喃酰溴在对构空间群中的结晶。
IF 2.5 3区 化学
Carbohydrate Research Pub Date : 2025-10-03 DOI: 10.1016/j.carres.2025.109693
Grzegorz Detlaff , Artur Sikorski , Jarosław Chojnacki , Beata Liberek
{"title":"Crystallisation of 2,3,4-tri-O-acetyl-α-d- and α-l-xylopyranosyl bromides in enantiomorphic space groups","authors":"Grzegorz Detlaff ,&nbsp;Artur Sikorski ,&nbsp;Jarosław Chojnacki ,&nbsp;Beata Liberek","doi":"10.1016/j.carres.2025.109693","DOIUrl":"10.1016/j.carres.2025.109693","url":null,"abstract":"<div><div>Bromoacetates of α-<span>d</span>-xylose and α-<span>l</span>-xylose, compounds from the group of extensively explored carbohydrate substrates, were synthesised and structurally characterised. Crystallographic studies performed for both compounds respectively indicate that this pair of enantiomers crystallises in the pair of enantiomorphic space groups, <em>P</em>4<sub>1</sub>2<sub>1</sub>2 and <em>P</em>4<sub>3</sub>2<sub>1</sub>2, respectively. The chirality of these space groups is induced by the helical arrangement of the bromides in the crystals. Geometry of the synthesised bromoacetates is discussed based on crystallographic data and calculations performed using DFT methods. It was proved that the anomeric effect acts and that the acetyl groups are characteristically arranged in the bromoacetates.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"558 ","pages":"Article 109693"},"PeriodicalIF":2.5,"publicationDate":"2025-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145291260","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
Characterization and discrimination of polysaccharides from three Atractylodes spp. based on multiple structural information 基于多重结构信息的三种苍术属多糖的鉴定与鉴别
IF 2.5 3区 化学
Carbohydrate Research Pub Date : 2025-10-03 DOI: 10.1016/j.carres.2025.109694
Si-si Jia , Zi-wei Han , Hui-yang Wang , Yv-jie Wu , Mei-juan Zhao , Hong-wei Qiu , He-he Li , Fei Chen , Guang-ping Lv
{"title":"Characterization and discrimination of polysaccharides from three Atractylodes spp. based on multiple structural information","authors":"Si-si Jia ,&nbsp;Zi-wei Han ,&nbsp;Hui-yang Wang ,&nbsp;Yv-jie Wu ,&nbsp;Mei-juan Zhao ,&nbsp;Hong-wei Qiu ,&nbsp;He-he Li ,&nbsp;Fei Chen ,&nbsp;Guang-ping Lv","doi":"10.1016/j.carres.2025.109694","DOIUrl":"10.1016/j.carres.2025.109694","url":null,"abstract":"<div><div>Polysaccharides from 18 batches of <em>Atractylodes lancea</em> (AL), <em>A. chinensis</em> (AC) and <em>A. macrocephala</em> (AM) were compared based on molecular weight (MW) distribution, monosaccharide composition and content, and glycosidic linkage type. Results showed that polysaccharides from AL, AC and AM mainly exhibited three molecular weight fractions, and the average Mw of fraction 1 and 2 in AM is 4.0–1.8 times of AL and AC. Therefore, AM could be distinguished from AL and AC based on large Mw. 7 kinds of monosaccharides were released from AL, AC and AM, and the average content of released monosaccharides in AC (141.2 mg/g) was obviously higher than that in AL (106.4 mg/g) and AM (121.0 mg/g). AC could be distinguished from AL based on monosaccharides content. 1,2-Fru<em>f</em> is the dominant type of glycosidic linkage, which indicated that fructan is abundant. The higher proportion of 1,4-Gal<em>p</em> residues after reduction in AM revealed that pectin-type polysaccharides are relatively abundant in AM. Combined with chemometric analysis, the glycosidic linkage can distinguish AL, AC and AM clearly, and 1, 4-Gal<em>p</em> and 1,2,4-Rha<em>p</em> residues were confirmed as the differential glycosidic linkages. This study was helpful in understanding the varied functions of different <em>Atractylodes</em> spp. based on chemical composition.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"558 ","pages":"Article 109694"},"PeriodicalIF":2.5,"publicationDate":"2025-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145263124","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
Deoxygenated analogs of 2-deoxy-2,3-didehydro-N-acetyl neuraminic acid as inhibitors of human neuraminidase enzymes 2-脱氧-2,3-二脱氢- n -乙酰神经氨酸的脱氧类似物作为人神经氨酸酶抑制剂。
IF 2.5 3区 化学
Carbohydrate Research Pub Date : 2025-10-02 DOI: 10.1016/j.carres.2025.109691
Nahoko Yagami, Fatma Eljabu, Manas Jana, Elisa G. Carvajal, Christopher W. Cairo
{"title":"Deoxygenated analogs of 2-deoxy-2,3-didehydro-N-acetyl neuraminic acid as inhibitors of human neuraminidase enzymes","authors":"Nahoko Yagami,&nbsp;Fatma Eljabu,&nbsp;Manas Jana,&nbsp;Elisa G. Carvajal,&nbsp;Christopher W. Cairo","doi":"10.1016/j.carres.2025.109691","DOIUrl":"10.1016/j.carres.2025.109691","url":null,"abstract":"<div><div>There is increasing interest in carbohydrate analogs for drug development, and the polar nature of these targets presents a challenge for medicinal chemistry. Multiple substrate hydroxy groups are typically required for enzyme active site recognition. Not all of these polar groups will have the same importance in recognition. A common strategy is to replace or remove these groups and compare the activity of the resulting analogs. If hydroxy groups are non-essential, or if their removal results in increased potency they may form the basis of improved inhibitors or substrates. In our studies of human neuraminidase enzymes (NEU), we have identified modifications at the C5 and C9 positions of the 2-deoxy-2,3-didehydro-<em>N</em>-acetyl neuraminic (DANA) scaffold that provide potent and selective inhibitors. In this study, we sought to test the requirements of each of the four human NEU isoenzymes for the presence of O4, O7, O8, or O9 hydroxy groups found in DANA. We synthesized the corresponding mono- (4, 7, 8, and 9) and di-deoxy (7,9; 7,8; and 8,9) analogs of DANA and tested their potency against human NEU. We found that 8-deoxy compounds increased potency against NEU2 and NEU3. Additionally, several di-deoxy analogs were tolerated by NEU1, NEU2, and NEU3. Finally, we generated known selective inhibitors of NEU3 and NEU4 and tested their 8-deoxy analogs. Combination of these features did not improve overall potency, suggesting deoxygenated analogs will require additional optimization.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"558 ","pages":"Article 109691"},"PeriodicalIF":2.5,"publicationDate":"2025-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145312489","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 of Ara-β-(1 → 2)-Ara diarabinofuranosides with O-TBDPS protective groups in the synthesis of the tetra- and dodecaarabinofuranosides - fragments of mycobacterial polysaccharides. 带O-TBDPS保护基团的Ara-β-(1→2)-Ara二糖苷在分枝杆菌多糖四、十二糖苷片段合成中的应用
IF 2.5 3区 化学
Carbohydrate Research Pub Date : 2025-10-01 Epub Date: 2025-07-30 DOI: 10.1016/j.carres.2025.109622
Polina I Abronina, Dmitry S Novikov, Nelly N Malysheva, Alexander I Zinin, Natalia G Kolotyrkina, Leonid O Kononov
{"title":"Application of Ara-β-(1 → 2)-Ara diarabinofuranosides with O-TBDPS protective groups in the synthesis of the tetra- and dodecaarabinofuranosides - fragments of mycobacterial polysaccharides.","authors":"Polina I Abronina, Dmitry S Novikov, Nelly N Malysheva, Alexander I Zinin, Natalia G Kolotyrkina, Leonid O Kononov","doi":"10.1016/j.carres.2025.109622","DOIUrl":"10.1016/j.carres.2025.109622","url":null,"abstract":"<p><p>The synthesis of Ara-β-(1 → 2)-Ara glycosyl donor containing TBDPS groups starting from the corresponding glycoside with 4-(3-azidopropoxy)phenyl aglycone was performed in high yield. The obtained glycosyl donor was successfully used in the stereocontrolled synthesis of 4-(2-azidoethoxy)phenyl glycosides of linear β-(1 → 2)-, α-(1 → 5)-tetra- and branched β-(1 → 2)-, α-(1 → 3)-, α-(1 → 5)-linked dodecaarabinofuranosides related to the fragments of mycobacterial polysaccharides. These compounds are valuable for the preparation of conjugates that can be used as antigens in the diagnosis of mycobacterial infections. The synthesis of Ara-β-(1 → 2)-Ara glycosyl donor containing TBDPS groups starting from 4-(2-chloropropoxy)phenyl glycoside was found to be less efficient due to side reactions in course of manipulations with protective groups. Thus, during the treatment with TBAF, 4-(3-chloropropoxy)phenyl aglycone was partially converted to the product of substitution (4-(3-fluoropropoxy)phenyl) and elimination (4-allyloxyphenyl). In the course of silylation (TBDPS-Cl/imidazole), the formation of 4-[3-(imidazole-1-yl)propoxy]phenyl derivative was observed.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"556 ","pages":"109622"},"PeriodicalIF":2.5,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144798220","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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