Carbohydrate Research最新文献_第8页

Preparation, structural characterization, and pharmacological applications of polysaccharides from the genus Aconitum: A review 乌头多糖的制备、结构表征及药理应用综述。

IF 2.5 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research

Pub Date : 2026-01-01 Epub Date: 2025-11-05 DOI: 10.1016/j.carres.2025.109736

Zhimin Jian , Mingyang Cao , Fangyu Li , Yonghui Rui , Feiya Zhao , Aien Tao

There are approximately 350 species of Aconitum worldwide, primarily distributed in the northern temperate zone, with a significant presence in Asia. Modern pharmacological studies have demonstrated that Aconitum polysaccharides (APS) exhibit a range of biological activities, including immune enhancement, hypoglycemic effects, anti-inflammatory properties, antitumor activity, antioxidant effects, and cholesterol-lowering capabilities. These attributes have positioned APS at the forefront of research focused on their development and application, indicating a promising future in the fields of biomedicine and functional foods. Furthermore, the methods employed for extraction, isolation, and purification can substantially influence the content, purity, and subsequent structural characterization of APS, thereby affecting their biological activities. Despite their significance, a comprehensive review of APS is currently lacking. Given the critical role of these polysaccharides in biological research and drug development, this review aims to gather and synthesize information regarding extraction, isolation, and purification methods, structural characterization, pharmacological activities, and potential mechanisms of action of polysaccharides derived from Aconitum, utilizing various literature databases up to the publication date of this review. This paper seeks to provide a theoretical foundation and technical guidance for the development of APS into biopharmaceuticals, functional foods, and biomaterials.

全世界约有350种乌头属植物，主要分布于北温带，在亚洲也有大量分布。现代药理学研究表明，乌头多糖（APS）具有多种生物活性，包括免疫增强、降糖作用、抗炎作用、抗肿瘤作用、抗氧化作用和降胆固醇能力。这些特性使APS处于研究开发和应用的前沿，在生物医药和功能食品领域具有广阔的应用前景。此外，用于提取、分离和纯化的方法可以实质性地影响APS的含量、纯度和随后的结构表征，从而影响其生物活性。尽管其意义重大，但目前缺乏对APS的全面审查。鉴于乌头多糖在生物学研究和药物开发中的重要作用，本文旨在利用截至本文发表之日的各种文献数据库，收集和综合乌头多糖的提取、分离、纯化方法、结构表征、药理活性和潜在作用机制等方面的信息。本文旨在为APS在生物制药、功能食品、生物材料等领域的发展提供理论基础和技术指导。

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引用次数: 0

Investigation of the bioactivities of N, N, N-trimethyl chitosan derivatives constructed with sulfonic zwitterionic moieties 巯基两性离子结构的N， N， N-三甲基壳聚糖衍生物的生物活性研究

IF 2.5 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research

Pub Date : 2026-01-01 Epub Date: 2025-10-29 DOI: 10.1016/j.carres.2025.109721

Yonggang Peng , Ying Yu , Zhongwen Su , Yujing Zhong , Yikai Chen , Yangfan Mao , Sekar Vijayakumar , Meihua Xin , Mingchun Li

In this work, a novel class of sulfonic zwitterion-modified quaternary ammonium chitosan derivatives was prepared using N, N, N-trimethyl chitosan (TMCI) as the structural backbone. To verify the successful synthesis, the resulting compounds were comprehensively analyzed in terms of their molecular configurations, thermal behavior, and crystalline properties. Characterization techniques included Fourier-transform infrared (FTIR) spectroscopy, proton nuclear magnetic resonance (¹H NMR), thermogravimetric analysis (TGA), and X-ray diffraction (XRD). Antibacterial performance was comprehensively evaluated through minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC), and inhibition rate assessments against both Gram-negative Escherichia coli and Gram-positive Staphylococcus aureus, revealing enhanced antibacterial activity following modification. Antioxidant properties were examined through DPPH, superoxide, and hydroxyl radical scavenging assays, all of which confirmed strong free radical elimination. Furthermore, cytocompatibility tests verified excellent biocompatibility, underscoring their safety for biomedical applications. Collectively, these results highlight the critical role of structural modification in regulating the bioactivity of chitosan-based systems. The multifunctional properties of these derivatives—including potent antimicrobial activity, effective oxidative stress mitigation, and favorable biocompatibility—provide a strong foundation for their potential use in biomedical materials, smart packaging, and preservation technologies.

本文以N， N， N-三甲基壳聚糖（TMCI）为骨架，制备了一类新型的磺化两性离子改性季铵盐壳聚糖衍生物。为了验证成功的合成，所得到的化合物在分子构型、热行为和晶体性质方面进行了全面的分析。表征技术包括傅里叶变换红外（FTIR）光谱、质子核磁共振（1H NMR）、热重分析（TGA）和x射线衍射（XRD）。通过对革兰氏阴性大肠杆菌和革兰氏阳性金黄色葡萄球菌的最低抑菌浓度（MIC）、最低杀菌浓度（MBC）和抑制率评估，综合评价其抗菌性能，发现改性后抗菌活性增强。通过DPPH，超氧化物和羟基自由基清除实验检测抗氧化性能，所有这些都证实了强自由基清除。此外，细胞相容性测试证实了出色的生物相容性，强调了其生物医学应用的安全性。总的来说，这些结果强调了结构修饰在调节壳聚糖基系统的生物活性中的关键作用。这些衍生物的多功能特性——包括有效的抗菌活性、有效的氧化应激缓解和良好的生物相容性——为它们在生物医学材料、智能包装和保存技术中的潜在应用奠定了坚实的基础。

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引用次数: 0

Recent advances in glyco-nanoparticles for probing the glyco-codes of cancer 糖纳米粒子探测癌症糖密码的最新进展。

IF 2.5 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research

Pub Date : 2026-01-01 Epub Date: 2025-11-14 DOI: 10.1016/j.carres.2025.109757

A.K.M. Atique Ullah , Xuefei Huang

Aberrant glycosylation is a hallmark of cancer, producing tumor-associated carbohydrate antigens (TACAs) and altering cell-surface interactions that reshape adhesion, signaling, and immune recognition. These altered glycans, collectively referred to as the “cancer glyco-code”, represent unique glycan expression patterns that create actionable targets for diagnosis and therapy. The glycan-binding proteins that recognize and interpret these structures, termed the “readers” of the glyco-code, include lectin families such as Siglecs, galectins, selectins, and cluster of differentiation 44 (CD44). Glyco-nanoparticles (GlycoNPs) are inspired by glyco-code and designed to probe these readers by multivalently presenting tumor-relevant glycans on engineered cores (gold, iron oxide, polymers), thereby boosting avidity and selectivity in cancer targeting. This review distills design principles for GlycoNPs’ core selection, conjugation chemistry, glycan density/orientation, and multivalency control, and reviews applications in surface-enhanced Raman scattering (SERS), magnetic resonance imaging (MRI), high-throughput glycan binding screens, and targeted drug delivery. We highlight immune-modulatory strategies (e.g., Siglec decoying, galectin blockade, and glycan-guided macrophage reprogramming) that position GlycoNPs as “glycan immune checkpoints.” We also examine translational bottlenecks: inter- and intra-tumoral glycan heterogeneity; manufacturing reproducibility (density/orientation/valency); colloidal and biological stability; pharmacokinetics; and regulatory expectations for characterization and immunogenicity. Finally, we outline emerging applications that may accelerate bench-to-bedside translation. Overall, GlycoNPs offer a modular, multiplexable path to precision oncology, enabling reader-guided tumor profiling, imaging, and intervention through the language of glycans.

异常糖基化是癌症的一个标志，产生肿瘤相关碳水化合物抗原（TACAs），改变细胞表面相互作用，重塑粘附、信号传导和免疫识别。这些改变的聚糖，统称为“癌症糖密码”，代表了独特的聚糖表达模式，为诊断和治疗创造了可操作的靶点。识别和解释这些结构的聚糖结合蛋白被称为糖密码的“读者”，包括凝集素家族，如Siglecs、凝集素、选择素和分化簇44 （CD44）。糖纳米颗粒（GlycoNPs）受到糖密码的启发，设计用于通过在工程核心（金，氧化铁，聚合物）上多价呈现肿瘤相关聚糖来探测这些读取器，从而提高癌症靶向的亲切性和选择性。本文综述了GlycoNPs的核心选择、偶联化学、聚糖密度/取向和多价控制的设计原则，并综述了其在表面增强拉曼散射（SERS）、磁共振成像（MRI）、高通量聚糖结合筛选和靶向给药方面的应用。我们强调免疫调节策略（例如，Siglec诱骗，凝集素阻断和聚糖引导的巨噬细胞重编程），将GlycoNPs定位为“聚糖免疫检查点”。我们还研究了翻译瓶颈：肿瘤间和肿瘤内聚糖异质性；制造再现性（密度/取向/价）；胶体和生物稳定性；药物动力学;以及对表征和免疫原性的监管期望。最后，我们概述了新兴的应用程序，可以加速从实验室到病床的转换。总的来说，glyconp为精确肿瘤学提供了一个模块化的、可多路的途径，通过聚糖的语言实现了读者引导的肿瘤分析、成像和干预。

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引用次数: 0

Structural elucidation of fructose-based carbohydrates isolated from Atractylis aristata n-butanol extract with in vitro and in silico assessment of dual α-amylase inhibition and yeast cytotoxicity 从白术正丁醇萃取物中分离的果糖基碳水化合物的结构分析，体外和室内对双α-淀粉酶抑制和酵母细胞毒性的评价。

IF 2.5 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research

Pub Date : 2026-01-01 Epub Date: 2025-10-30 DOI: 10.1016/j.carres.2025.109720

Asma Abid , Oussama Khaoua , Mahdi Belguidoum , Tatou Touahria , Nour Elhouda Mekhedmi , kamilia Birech

This study presents the first detailed structural and biological characterization of fructose-based oligosaccharides Atractylis aristata is a medicinal plant, the saccharide composition of which remains largely uncharacterized. Four saccharides, ranging from mono-to trisaccharides, were isolated from the n-butanol extract and structurally elucidated using 1D and 2D NMR spectroscopy. The identified compounds were β-D-fructofuranoide (S1), β-d-fructopyranosyl-(2 → 1)-d-fructofuranose (S2), β-d-fructofuranosyl-(2 → 1)-α-d-glucopyranoside (Sucrose) (S3), and O-β-d-fructofuranosyl-(2 → 6)-β-d-fructofuranosyl-(2 → 1)-α-d-glucopyranoside (6-kestose) (S4). Biological screening included α-amylase inhibition assays and cytotoxicity evaluation using a yeast (Saccharomyces cerevisiae) model. Among the tested compounds, 6-kestose exhibited the strongest α-amylase inhibitory activity (IC₅₀ = 79.099 μg/mL), surpassing acarbose (IC₅₀ = 155.45 μg/mL), while no cytotoxic effects were observed even at high concentrations. Complementary computational analyses confirmed the stability and reactivity of the saccharides, emphasizing the role of hydroxyl and fructofuranosyl groups in enzyme binding. Frontier molecular orbital and electrostatic potential mapping revealed high molecular stability and well-distributed charge density, while molecular docking and dynamics simulations demonstrated strong and stable interactions of 6-kestose with catalytic residues Asp197 and Glu233. These findings establish A. aristata as a promising and safe natural source of α-amylase inhibitors, offering valuable molecular insights for the future development of antidiabetic agents.

本研究首次详细介绍了以果糖为基础的低聚糖的结构和生物学特性。白术是一种药用植物，其糖的组成在很大程度上仍然是未知的。从正丁醇萃取物中分离出4种糖，从单糖到三糖不等，并通过1D和2D NMR进行了结构鉴定。经鉴定的化合物分别为β-d-聚呋喃烷醇（S1）、β-d-聚呋喃烷醇-(2→1)-d-聚呋喃烷醇（S2）、β-d-聚呋喃烷醇-(2→1)-α-d-聚呋喃烷醇（蔗糖）（S3）和O-β-d-聚呋喃烷醇-(2→6)-β-d-聚呋喃烷醇-(2→1)-α-d-聚呋喃烷醇（6-酮）（S4）。生物筛选包括α-淀粉酶抑制试验和酵母（Saccharomyces cerevisiae）模型的细胞毒性评价。其中，6-酮糖对α-淀粉酶的抑制作用最强（IC50 = 79.099 μg/mL），超过了阿卡波糖（IC50 = 155.45 μg/mL），即使在高浓度下也没有细胞毒作用。互补计算分析证实了糖的稳定性和反应性，强调了羟基和果糖呋喃基在酶结合中的作用。前沿分子轨道和静电势映射显示6-酮糖具有较高的分子稳定性和均匀的电荷密度，而分子对接和动力学模拟显示6-酮糖与催化残基Asp197和Glu233之间具有强而稳定的相互作用。这些发现表明，马兜铃是一种有前途的、安全的α-淀粉酶抑制剂天然来源，为未来开发抗糖尿病药物提供了有价值的分子见解。

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引用次数: 0

Functional characterization and effect of polysaccharides on the activity of GH16 β-agarase from Gelidibacter salicanalis PAMC21136 水杨胶杆菌PAMC21136中多糖对GH16 β-琼脂酶活性的影响及功能表征

IF 2.5 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research

Pub Date : 2026-01-01 Epub Date: 2025-10-28 DOI: 10.1016/j.carres.2025.109719

Lakshan Paudel , Bashu Dev Pardhe , Sushma Gupta , So-Ra Han , Jun Hyuck Lee , Tae-Jin Oh

β-agarase is the key enzyme for the primary degradation of agar, a major component of red algae. This study demonstrates cloning, overexpression and characterization of a recombinant GH16 β-agarase (WP_199597959) from Antarctic bacterium Gelidibacter salicanalis PAMC21136. Biochemical properties demonstrated that the maximum activity was observed at pH and temperature of 7.0 and 50°C, respectively using agarose as a substrate. The agarolytic activity of WP_199597959 on agarose was found to be endo-type with production of neoagarobiose (NA2) as a major product. Mn²⁺ metal ion significantly enhanced the activity, doubling the reaction rate as compared with other metal ions. Neoagarooligosaccharides (NAOSs) like neoagarotetraose (NA4), and neoagarohexaose (NA6) hydrolyzed into NA2. In-silico analysis demonstrated that the key catalytic residues E184 and E189 are involved in retaining hydrolytic mechanisms. In-vitro, interaction with negatively charged carboxymethyl cellulose (CMC) enhanced the enzyme activity by 15% while positively charged chitosan (CS) decreased the enzyme activity by 12%, highlighting the effect of biopolymers on enzyme activity within the microenvironment interaction. These findings may provide insight into biochemical properties and application of WP_199597959 for agarose degradation.

β-琼脂酶是红藻主要成分琼脂初级降解的关键酶。本研究从南极细菌Gelidibacter salicanalis PAMC21136中克隆、过表达重组GH16 β-琼脂酶（WP_199597959）并对其进行了鉴定。以琼脂糖为底物，在pH为7.0、温度为50℃时活性最高。发现WP_199597959对琼脂糖的溶糖活性为内溶型，主要产物为新琼脂糖（NA2）。Mn2+金属离子显著提高了反应活性，反应速率是其他金属离子的两倍。新琼脂低聚糖（NAOSs）如新琼脂四糖（NA4）和新琼脂己糖（NA6）水解成NA2。硅分析表明，关键催化残基E184和E189参与保持水解机制。在体外，与带负电的羧甲基纤维素（CMC）相互作用，酶活性提高了15%，而带正电的壳聚糖（CS）使酶活性降低了12%，这突出了生物聚合物对微环境相互作用中酶活性的影响。这些发现为WP_199597959降解琼脂糖的生化特性及应用提供了新的思路。

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引用次数: 0

Optimization, characterization and application of chitooligosaccharide-urea conjugate for wheat seed priming: A sustainable approach 壳寡糖-尿素偶联物的优化、表征及应用：一种可持续的方法

IF 2.5 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research

Pub Date : 2026-01-01 Epub Date: 2025-10-30 DOI: 10.1016/j.carres.2025.109722

Surbhi Sahewalla , Sonam Sihag , Yamini Tak , Anil Duhan , Vinod Saharan , Ajay Pal

The present study deals with the preparation of chitooligosaccharide (COS), its conjunction with urea, and its priming effect on wheat grains. Employing central composite rotatable design (CCRD) of response surface methodology (RSM) to optimize conditions for COS production resulted in COS with a reducing sugar: 4.14 mg GAH/ml and an average particle size: 232 nm. FTIR, FESEM and XRD validated its formation. The COS displayed exceptional antioxidant properties via. DPPH (IC₅₀: 7.74 mg/ml), ABTS (IC₅₀: 0.147 mg/ml), MCA (IC₅₀: 0.329 mg/ml) and TAA (AO_0.5: 1.76 mg/ml). It was then dopped with urea, and FTIR and NMR detailed the interaction between COS and urea, primarily owing to hydrogen bonds. On studying the effect of priming of wheat grains, an increase of 41.5 % and 22.62 % in shoot and root length of wheat seedlings was noticed with COS-urea (25–50 ppm). Fresh weight, dry weight, SVI-I and SVI-II also detailed the maximum positive trend with COS-urea followed by the maximum utilization of starch and protein. This study provides a new perspective on the application of COS-urea for enhancing the germination potential of wheat, and also for its potential use as a foliar spray, contributing towards sustainable agriculture and the environment.

本文研究了壳寡糖（COS）的制备、与尿素的结合及其对小麦籽粒的激发作用。采用响应面法（RSM）的中心复合旋转设计（CCRD）优化COS的生产条件，得到COS的还原糖为4.14 mg GAH/ml，平均粒径为232 nm。FTIR、FESEM和XRD验证了其形成。COS表现出优异的抗氧化性能。DPPH （IC50: 7.74 mg/ml）、ABTS （IC50: 0.147 mg/ml）、MCA （IC50: 0.329 mg/ml）和TAA （AO0.5: 1.76 mg/ml）。然后加入尿素，FTIR和NMR详细描述了COS和尿素之间的相互作用，主要是由于氢键。在对小麦籽粒催肥效果的研究中，cos -尿素（25-50 ppm）可使小麦幼苗的茎长和根长分别增加41.5%和22.62%。鲜重、干重、SVI-I和SVI-II均随cos -尿素呈最大正相关，其次是淀粉和蛋白质的最大利用率。本研究为利用cos -尿素提高小麦发芽率和叶面喷施提供了新的思路，为可持续农业和环境保护做出贡献。

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引用次数: 0

Lipooligosaccharide architecture in Acinetobacter modestus CM11G: a non-pathogenic strain 温和不动杆菌CM11G的脂低糖结构：一种非致病性菌株。

IF 2.5 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research

Pub Date : 2026-01-01 Epub Date: 2025-11-11 DOI: 10.1016/j.carres.2025.109743

Immacolata Speciale , Luisa Sturiale , Angelo Palmigiano , Anna Notaro

The Acinetobacter genus comprises a multitude of species that have been isolated from both environmental and clinical samples. In recent years, the scientific community has expended considerable effort in characterising the structures of the capsular polysaccharides and lipooligoaccharides (LOS) of A. baumannii, given the increasing mortality rate caused by this species. Comparatively little research has been undertaken for the non-pathogenic species.

In the present study, we describe the first case of isolation and identification of the LOS molecule of Acinetobacter modestus CM11G, a Gram-negative bacterium colonising the intestinal crypts of a healthy mouse. By combining spectroscopic and spectrometric analyses with chemical derivatisations, we were able to determine the structure of the entire LOS. The lipid A moiety is composed mainly of hepta-acylated species, a characteristic also observed in other Acinetobacter species. It is extended with a disaccharide of Kdo, which acts as a bridge between the lipid A and the oligosaccharide portion. Indeed, the internal Kdo residue is linked at position O-5 with a novel tetrasaccharide composed of βGlcN(1→2)-βGal(1→6)-αGlc(1→, where the glucose is further substituted at position O-4 with a terminal β-Glc. In contrast, the external Kdo residue does not undergo further substitution, contrary to what generally occurs in the LOS of A. baumannii.

不动杆菌属包括从环境和临床样本中分离出来的多种物种。近年来，鉴于鲍曼不动杆菌造成的死亡率不断上升，科学界花费了相当大的努力来表征鲍曼不动杆菌的荚膜多糖和低脂多糖（LOS）的结构。相对而言，对非致病性物种的研究很少。在本研究中，我们首次分离和鉴定了一种定殖于健康小鼠肠隐窝的革兰氏阴性细菌——温和不动杆菌CM11G的LOS分子。通过将光谱和光谱分析与化学衍生相结合，我们能够确定整个LOS的结构。脂质A部分主要由七酰化的种类组成，这一特征在其他不动杆菌种类中也观察到。它与Kdo的双糖延伸，它作为脂质a和低聚糖部分之间的桥梁。实际上，内部的Kdo残基在O-5位置与一个由βGlcN(1→2)-βGal(1→6)-αGlc（1→）组成的新型四糖相连，其中葡萄糖在O-4位置进一步被末端的β-Glc取代。相反，外部的Kdo残基不经历进一步的替代，这与鲍曼不动杆菌的LOS中通常发生的情况相反。

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引用次数: 0

Unexpected formation of furanose form during deacetylation of pyranose glyco-oxazolines 在吡喃糖-恶唑啉去乙酰化过程中意外形成呋喃糖。

IF 2.5 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research

Pub Date : 2026-01-01 Epub Date: 2025-11-19 DOI: 10.1016/j.carres.2025.109761

Maxim A. Romanyuk, Ilya V. Myachin, Maria V. Panova, Alexander I. Zinin, Oleg R. Malyshev, Natalya G. Kolotyrkina, Leonid O. Kononov

We have found that the deacetylation of O-acetylated pyranose glyco-oxazoline, derived from N-acetyl-d-glucosamine, using MeONa or other bases (Et₃N, K₂CO₃) in MeOH, selectively gives the expected pyranose triol at 20 °C. In contrast, at 60 °C, a previously unknown, thermodynamically favored furanose isomer of the glyco-oxazoline triol is formed. Isomeric O-acetylated pyranose glyco-oxazolines, derived from N-acetyl-d-galactosamine or N-acetyl-d-mannosamine, also afford furanose isomers of the corresponding glyco-oxazoline triols upon treatment with MeONa in MeOH at 60 °C. The obtained unprotected furanose glyco-oxazoline with gluco-configuration was transformed into O-acetylated furanose gluco-oxazoline. The ability to prepare (un)protected furanose glyco-oxazolines opens a novel pathway to the underexplored furanose forms of glyco-oxazolines bearing various O-protective groups.

我们发现，n -乙酰-d-氨基葡萄糖衍生的o-乙酰化吡喃糖-恶唑啉，在MeOH中使用MeONa或其他碱（Et3N, K2CO3），在20°C下选择性地得到预期的吡喃糖三醇。相反，在60℃时，形成了一种以前未知的、热力学上受欢迎的糖-恶唑啉三醇的呋喃糖异构体。由n -乙酰-d-半乳糖胺或n -乙酰-d-甘露糖胺衍生的o-乙酰化吡喃糖-恶唑啉异构体，在60°C的甲醇中用MeONa处理后，也能产生相应的糖-恶唑啉三醇的呋喃糖异构体。将得到的无保护型呋喃糖-恶唑啉转化为o-乙酰化呋喃糖-恶唑啉。制备（不）受保护的呋喃糖糖恶唑啉的能力为具有各种o保护基团的糖恶唑啉的呋喃糖形式开辟了一条新途径。

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引用次数: 0

A ‘chiron’ approach to divergent synthesis of 2-C-tridecyl 1-N-iminosugar mimetics and their anticancer profile 2- c -三烷基1- n -亚糖模拟物的“chiron”方法及其抗癌特性。

IF 2.5 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research

Pub Date : 2026-01-01 Epub Date: 2025-11-13 DOI: 10.1016/j.carres.2025.109742

Monika Tvrdoňová , Peter Michalčin , Tatiana Pončáková , Yuliia Zuzak , Martina Bago Pilátová , Juraj Kuchár , Miroslava Litecká , Miroslava Martinková

Two approaches leading to 2-C-tridecyl piperidine-containing 1-N-iminosugars from the chiral pool were accomplished. The pivotal steps for completing the construction of these azasugars were aza-Claisen rearrangements as a powerful tool for the formation of carbon-nitrogen bonds, cyclisation protocols and an olefin cross-metathesis. The versatility of the developed concept permits access to other stereoisomeric partners of this class of compounds by varying the sugar unit used as the starting material. Moreover, the late-stage introduction of an alkyl branch could provide high flexibility for novel side chain analogues. Last but not least, carbohydrates are a cost-effective, environmentally biocompatible starting material for the chiral pool strategy. The preliminary cytotoxic evaluation indicates that the designed piperidines have a promising capacity to alter the viability of cancer cell lines.

完成了从手性池中得到含2- c -三烷基哌啶- 1- n -亚氨基糖的两种方法。完成这些偶氮糖构建的关键步骤是偶氮糖- clisen重排作为形成碳-氮键的有力工具，环化协议和烯烃交叉复分解。所开发概念的多功能性允许通过改变用作起始材料的糖单位来获得该类化合物的其他立体异构体伙伴。此外，烷基分支的后期引入可以为新的侧链类似物提供高的灵活性。最后但并非最不重要的是，碳水化合物是一种具有成本效益，环境生物相容性的手性池策略起始材料。初步的细胞毒性评价表明，所设计的哌啶具有改变癌细胞存活能力的前景。

引用次数: 0

Structural diversity of the OPSs isolated from the LPSs of the plant pathogenic bacteria Pectobacterium parmentieri IFB5441 and IFB5533 植物致病菌Pectobacterium parmentieri IFB5441和IFB5533的lps分离产物的结构多样性

IF 2.5 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research

Pub Date : 2026-01-01 Epub Date: 2025-11-19 DOI: 10.1016/j.carres.2025.109762

Karolina Ossowska , Natalia Kaczyńska , Agnieszka Kowalczyk , Tomasz Apanowicz , Zbigniew Kaczyński

Pectobacterium parmentieri is a pectinolytic pathogenic bacterium causing high economic losses in plant crops. Lipopolysaccharide is one of the bacterial virulence factors that play an important role in plant colonisation and interaction with host defence systems. The chemical structure of an O-polysaccharide isolated from the lipopolysaccharide of the P. parmentieri IFB5441 was determined using NMR spectroscopy and chemical methods. The repeating unit of the O-polysaccharide was composed of three galactose residues and one residue of 5,7-diamino-3,5,7,9-tetradeoxy-l-glycero-l-manno-non-2-ulosonic acid:

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The chemical structure of the repeating unit of the O-polysaccharide isolated from the P. parmentieri IFB5533 was also determined revealing the presence of galactose, N-acetylgalactosamine and N-acetylmannosamine:

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果胶杆菌是一种对农作物造成巨大经济损失的果胶溶解致病菌。脂多糖是细菌的毒力因子之一，在植物定植和与宿主防御系统的相互作用中起着重要作用。采用核磁共振波谱和化学方法对从parmentieri IFB5441脂多糖中分离得到的o -多糖进行了化学结构分析。o-多糖的重复单元由三个半乳糖残基和一个5,7-二氨基-3,5,7,9-四tradeoxy-l-甘油-l-甘露-非2-ulosonic酸残基组成。下载：下载高分辨率图片（46KB）下载：下载完整尺寸图片从P. parmentieri IFB5533中分离的o-多糖的重复单元的化学结构也被确定，揭示了半乳糖、n-乙酰半乳糖胺和n-乙酰甘露糖胺的存在。下载高清图片（39KB）下载：下载全尺寸图片

{"title":"Structural diversity of the OPSs isolated from the LPSs of the plant pathogenic bacteria Pectobacterium parmentieri IFB5441 and IFB5533","authors":"Karolina Ossowska , Natalia Kaczyńska , Agnieszka Kowalczyk , Tomasz Apanowicz , Zbigniew Kaczyński","doi":"10.1016/j.carres.2025.109762","DOIUrl":"10.1016/j.carres.2025.109762","url":null,"abstract":"<div><div><em>Pectobacterium parmentieri</em> is a pectinolytic pathogenic bacterium causing high economic losses in plant crops. Lipopolysaccharide is one of the bacterial virulence factors that play an important role in plant colonisation and interaction with host defence systems. The chemical structure of an O-polysaccharide isolated from the lipopolysaccharide of the <em>P. parmentieri</em> IFB5441 was determined using NMR spectroscopy and chemical methods. The repeating unit of the O-polysaccharide was composed of three galactose residues and one residue of 5,7-diamino-3,5,7,9-tetradeoxy-<span>l</span>-glycero-<span>l</span>-manno-non-2-ulosonic acid:<span><figure><span><img><ol><li><span><span>Download: <span>Download high-res image (46KB)</span></span></span></li><li><span><span>Download: <span>Download full-size image</span></span></span></li></ol></span></figure></span></div><div>The chemical structure of the repeating unit of the O-polysaccharide isolated from the <em>P. parmentieri</em> IFB5533 was also determined revealing the presence of galactose, <em>N</em>-acetylgalactosamine and <em>N</em>-acetylmannosamine:<span><figure><span><img><ol><li><span><span>Download: <span>Download high-res image (39KB)</span></span></span></li><li><span><span>Download: <span>Download full-size image</span></span></span></li></ol></span></figure></span></div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"559 ","pages":"Article 109762"},"PeriodicalIF":2.5,"publicationDate":"2026-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145621023","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}

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