{"title":"Residue-specific protein-glycan conjugation strategies for the development of pharmaceutically promising glycoconjugate vaccines: A recent update","authors":"Rajib Sarkar , Ayan Bandyopadhyay , Goutam Brahmachari","doi":"10.1016/j.carres.2025.109476","DOIUrl":"10.1016/j.carres.2025.109476","url":null,"abstract":"<div><div>Covalent coupling between a carbohydrate antigen and a protein carrier leads to the formation of pharmaceutically promising glycoconjugate vaccines. Most licensed glycoconjugate vaccines are acquired by random bioconjugation of native or sized glycans with the surface-exposed amino acid residues of proteins, such as lysine, cysteine, aspartic acid, glutamic amino acid, <em>etc</em>. In the last two decades, considerable momentum has been gained in the glycoconjugate vaccine development by discovering several residue-specific bioconjugation strategies. As a result, glycoconjugate chemistry reaches the verge of discovering well-defined and “real” homogeneous vaccines, which may be more potent to generate antimicrobial resistance against “bad-bugs”. Through this literature survey, we intend to highlight the state of the art of residue-specific bioconjugation of proteins with glycans to obtain glycoconjugate vaccines. The review will also identify a potential roadmap to address the gap and the prospects in the medicinal domain.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109476"},"PeriodicalIF":2.4,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143776440","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}
{"title":"Total synthesis of conjugation ready repeating unit of Acinetobacter baumannii strain K141 capsular polysaccharide via a [2 + 2] convergent approach","authors":"Sunil K. Yadav, Somnath Yadav","doi":"10.1016/j.carres.2025.109478","DOIUrl":"10.1016/j.carres.2025.109478","url":null,"abstract":"<div><div><em>Acinetobacter baumannii</em> is a well-known opportunistic gram-negative bacterium responsible for serious concerns to human health due to its high virulence and extensive resistance to numerous antibiotics such as carbapenem, colistin, tigecycline, and many more. Herein, we have conducted the first total synthesis of the repeating unit of <em>Acinetobacter baumannii</em> strain K141 via the convergent [2 + 2] approach featuring the coupling of β-L-Rhap-(1 → 4)-β-D-GlcpNAc and β-D-Galp-(1 → 3)-β-D-GlcpNAc units. The synthesis of the first disaccharide unit involved a stereoselective <em>cis</em>-rhamnosylation that was achieved via the picoloyl-induced hydrogen bond mediated aglycon delivery with high β-stereo control.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109478"},"PeriodicalIF":2.4,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143768169","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}
Jacqueline Onumah , Newlove A. Afoakwah , Peter Osei Boamah , Emmanuel Duah Osei , Anthony Amotoe-Bondzie
{"title":"Biological properties and application of chitosan and low molecular weight chitosan in food industry: A review","authors":"Jacqueline Onumah , Newlove A. Afoakwah , Peter Osei Boamah , Emmanuel Duah Osei , Anthony Amotoe-Bondzie","doi":"10.1016/j.carres.2025.109475","DOIUrl":"10.1016/j.carres.2025.109475","url":null,"abstract":"<div><div>Low molecular weight chitosan (LMWCHT) is a natural, non-toxic, biodegradable, and biocompatible polymer with a range of biological activities, including antioxidant, antibacterial, hypocholesterolemic, anti-obesity, cytotoxic, anti-cancer, anti-tumour, and anti-diabetic properties. This review paper focuses on the biological properties and the applications of LMWCHT in the food industry. The applications of LMWCHT as a food additive, food coating, food packaging material, and food biosensor are discussed in detail. Additionally, the importance of LMWCHT in the manufacture of nutraceuticals and functional foods, as well as its role in extending the shelf-life of agri-food products is explored.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109475"},"PeriodicalIF":2.4,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143738628","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}
{"title":"A short synthesis of carbohydrate derived N-benzyl aminocyclopentitols through N-O bond cleavage of the corresponding isoxazolidine derivatives: Evaluation of their anticancer properties using in vitro and in silico studies","authors":"Tapas Halder , Rituparna Ghosh , Alaka Sahoo , Shasank Sekhar Swain , Ratul Hore , Sourav Ghosh , Prosenjit Saha , Joykrishna Maity","doi":"10.1016/j.carres.2025.109465","DOIUrl":"10.1016/j.carres.2025.109465","url":null,"abstract":"<div><div>A short synthesis of a potent glycosidase inhibitor <em>N</em>-benzyl-<em>β-</em>D-<em>gluco</em> aminocyclopentitol along with its 2-deoxy, and orthogonally protected 2-<em>O</em>-benzyl, 1,2,3-tri-<em>O</em>-benzyl and 1,2,3-tri-<em>O</em>-acetyl analogues through carbohydrate derived cyclopentane-fused isoxazolidine derivatives has been described herein. The key steps involve NaI mediated vinylation of D-glucose derived 5,6-di-<em>O</em>-mesylated compounds in sealed tube to produce 5,6-dideoxy-l,2-<em>O</em>-isopropylidene-<em>α</em>-D-<em>xylo</em>-hexo-5-enofuranos derivatives in very good yields. Subsequent acetonide deprotection and stereoselective intramolecular nitrone cycloaddition (INC) reaction involving C-4-vinyl functionalities and the latent aldehyde moiety at C-1 yielded various cyclopentano-isoxazolidines. The <em>N-O</em> bond cleavage of the isoxazolidine rings produced the targeted aminocyclopentitols. <em>In vitro</em> anticancer activities of the isoxazolidines and <em>N</em>-benzyl aminocyclopentitols were performed and found only 1,2,3-tri-<em>O</em>-benzyl analogue (<strong>20c</strong>) of <em>N</em>-benzyl-<em>β-</em>D-<em>gluco</em> aminocyclopentitols emerged as potent anticancer agent with IC<sub>50</sub> value 54.90 μM. Furthermore, the molecular docking study confirmed that <strong>20c,</strong> compared with the other derivatives, scores higher binding affinity for all the targeted receptors<strong>,</strong> HSP90, PLK1, and TOP2A.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109465"},"PeriodicalIF":2.4,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143768170","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}
Evelina L. Zdorovenko , Elena N. Sigida , Andrey S. Dmitrenok , Svetlana A. Konnova , Yulia P. Fedonenko
{"title":"Structure of O-polysaccharide from the Azospirillum himalayense ptl-3T lipopolysaccharide","authors":"Evelina L. Zdorovenko , Elena N. Sigida , Andrey S. Dmitrenok , Svetlana A. Konnova , Yulia P. Fedonenko","doi":"10.1016/j.carres.2025.109471","DOIUrl":"10.1016/j.carres.2025.109471","url":null,"abstract":"<div><div>Lipopolysaccharide was extracted with hot aqueous phenol from cells of <em>Azospirillum himalayense</em> ptl-3<sup>T</sup>, a diazotrophic Gram-negative bacterium isolated from Himalayan valley soil, India. 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 established.</div><div>→3)-α-<span>l</span>-Fuc<em>p</em>-(1→3)-α-<span>l</span>-Fuc<em>p</em>-(1→3)-α-<span>d</span>-Rha<em>p</em>4NAc-(1→</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109471"},"PeriodicalIF":2.4,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143768171","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}
{"title":"Organocatalyzed O-glycosylation of glycosyl trichloroacetimidates donors: l-prolinethioamide as brønsted acid catalyst","authors":"Ashwani Tiwari , Ariza Khanam , Pintu Kumar Mandal","doi":"10.1016/j.carres.2025.109470","DOIUrl":"10.1016/j.carres.2025.109470","url":null,"abstract":"<div><div>In this study, we present the utilization of <span>l</span>-proline-derived thioamide small organic molecules as an effective organocatalyst for the O-glycosylation of various glycosyl trichloroacetimidate donors, eliminating the need for any cocatalysts or additives. The catalytic process achieves high yields with a wide array of alcohol and sugar nucleophiles, demonstrating a broad substrate scope and operational simplicity under mild reaction conditions. Preliminary mechanistic investigations indicate that <span>l</span>-prolinethioamide facilitates the glycosylation reaction via Brønsted acid/base catalysis, involving the formation of a catalyst–acceptor adduct.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109470"},"PeriodicalIF":2.4,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143738627","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}
Xiaoyun Wang , Xiaojun Liu , Chao Li , Jiangtao Li , Meng Qiu , Yongliang Wang , Wenwei Han
{"title":"Effects of molecular weights on the bioactivity of hyaluronic acid: A review","authors":"Xiaoyun Wang , Xiaojun Liu , Chao Li , Jiangtao Li , Meng Qiu , Yongliang Wang , Wenwei Han","doi":"10.1016/j.carres.2025.109472","DOIUrl":"10.1016/j.carres.2025.109472","url":null,"abstract":"<div><div>Hyaluronic acid (HA), the only non-sulfated glycosaminoglycan (GAG), is essential for maintaining the extracellular matrix's structural and functional integrity. Its bioactivity is determined by interactions between HA fragments of different molecular weights and specific receptors, which influence downstream signaling pathways. This review systematic summarizes the correlation between HA molecular weight dynamic changes and bioactivities focusing on imbalance of HA degradation and metabolism due to various pathological processes. Outline the core transduction mechanisms of HA receptors and signaling pathways, and innovatively hypothesize that discrepancies in cellular distribution with HA-molecular weights dependent lead to the activation of different signaling pathways from the perspective of molecular weight affecting cellular distribution. Finally, it addresses challenges in studying HA's biofunctions and provides new perspectives for future research.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109472"},"PeriodicalIF":2.4,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143776441","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}
{"title":"Biopolymeric starch-based matrix: A sustainable platform for slow release fertilizers","authors":"Mani Prabha , Puneet Tiwari , Pankaj Kumar Yadav , Vandana Singh , Devendra Narayan Tripathi , 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}
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 , 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","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}
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 , Christopher Hager , Holly Arcure , Jessie Lopez , Any M. Barrios Gomez , Zbigniew J. Witczak , Roman Bielski , 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}