Carbohydrate Research最新文献

{"title":"Synthesis of the conjugation ready tetrasaccharide repeating unit of the O-polysaccharide from Halomonas fontilapidosi KR26","authors":"Bijoy Rudra,&nbsp;Balaram Mukhopadhyay","doi":"10.1016/j.carres.2024.109371","DOIUrl":"10.1016/j.carres.2024.109371","url":null,"abstract":"<div><div>Synthesis of the tetrasaccharide repeating unit of the <em>O</em>-polysaccharide from <em>Halomonas fontilapidosi</em> KR26 was accomplished through a convergent [2 + 2]-block strategy using rationally protected monosaccharide synthons derived from commercially available sugars. The target tetrasaccharide was synthesized in the form of its 2-azidoethyl glycoside to ensure further conjugation with specific aglycons without hampering the reducing end stereochemistry. Use of only acyl/aryl protecting groups was targeted to keep the terminal azido-group intact for the utilization of “Click chemistry” for further conjugations.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"Article 109371"},"PeriodicalIF":2.4,"publicationDate":"2024-12-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142913707","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":"Drug release potential of polyacrylamide grafted-Assam Bora rice polysaccharide graft copolymer (ABRS-g-PAM) as effective controlled release polymer","authors":"Neha Singh ,&nbsp;Itishree Jogamaya Das ,&nbsp;Sutapa Satpathi ,&nbsp;Devjit Das ,&nbsp;Bhabani Shankar Patro ,&nbsp;Karmabeer Jena ,&nbsp;Subhendu Chakroborty ,&nbsp;Pankaj Dagar ,&nbsp;Trishna Bal","doi":"10.1016/j.carres.2024.109355","DOIUrl":"10.1016/j.carres.2024.109355","url":null,"abstract":"<div><div>The research focuses on the characterization and evaluation of drug delivery efficiency of a microwave-assisted, free-radical synthesized polyacrylamide-grafted Assam Bora rice starch (ABRS) graft copolymer (ABRS-g-PAM). Percentage grafting efficiency (% GE) and intrinsic viscosity were chosen as the optimization parameters. The optimized ABRS-g-PAM Grade Formulation 4 (GF4) was found to be the best grade. GF4 was characterized through XRD, FTIR, TGA, DSC, and ¹³C NMR, confirming efficient polyacrylamide grafting onto ABRS, besides swelling studies. SEM and FESEM showed a rough GF4 surface. Further analysis using Atomic Force Microscopy (AFM) detailed the irregular, rough internal architecture. The maximum swelling of GF4 occurred at pH 7 and 0.005 (M) NaCl, demonstrating second-order swelling kinetics. The soil biodegradability study of GF4 confirmed its biocompatibility. In vitro drug release studies showed that GF4 achieved 99 % release of Rosuvastatin over 26 h, thereby supporting the controlled release behaviour of the optimized polymer.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"Article 109355"},"PeriodicalIF":2.4,"publicationDate":"2024-12-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142892375","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":"Photo-responsive organogelator based on cholesterol incorporated sugar-azobenzene derivatives","authors":"Rabecca Jenifer V ,&nbsp;Jan Grzegorz Malecki ,&nbsp;Mohan Das Thangamuthu","doi":"10.1016/j.carres.2024.109356","DOIUrl":"10.1016/j.carres.2024.109356","url":null,"abstract":"<div><div>In this report, the design and synthesis of cholesterol-based sugar azobenzene derivatives as photo-responsive organogelators have been carried out. The gel formation in different solvents was examined, and a minimum CGC of 0.5 % (w/v) was attained in toluene. The mechanism of self-assembly of organogels was characterized by using ¹H NMR, UV–Vis, FT-IR, and PXRD. These organogelators show photo-isomerization and photo-reversible properties, which were studied using absorption spectra. Computational studies studied the optimized dimer structures and geometries of the trans and cis isomers. The prominent nature of this designed structure makes it an outstanding, intelligent soft material with plausible applications.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"Article 109356"},"PeriodicalIF":2.4,"publicationDate":"2024-12-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142887869","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":"Synthesis of branched heterooligosaccharides related to Aspergillus galactomannan containing short Galf side chains","authors":"Darya A. Rastrepaeva ,&nbsp;Dmitry A. Argunov ,&nbsp;Ilya A. Puchkin ,&nbsp;Dmitry V. Yashunsky ,&nbsp;Vadim B. Krylov ,&nbsp;Nikolay E. Nifantiev","doi":"10.1016/j.carres.2024.109360","DOIUrl":"10.1016/j.carres.2024.109360","url":null,"abstract":"<div><div>The members of a widespread <em>Aspergillus</em> fungi genus cause various diseases including the invasive aspergillosis with high morbidity and mortality rates, especially for immunosuppressed patients. One of the main carbohydrate structures on the surface of their cell wall is the galactomannan (GM) which is used in diagnostic kits for the detection of specific types of aspergillosis. However, limited specificity of currently available test systems urges the need for their further improvement. Herein we report the first synthesis of branched heterosaccharides related to GM and containing α-(1→2)-/α-(1→6)-linked tetramannoside backbone chain bearing one galactofuranoside unit or its β-(1→5)-linked dimer. The preparation of conjugates of the obtained spacered oligosaccharides with BSA is also performed to produce tools for the assessment the specificity of anti-<em>Aspergillus</em> immune response and to select antibodies suitable for the development of novel diagnostic kits that may discriminate distinct types of aspergillosis.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"Article 109360"},"PeriodicalIF":2.4,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142881438","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":"Advances in structural modification of fucoidans, ulvans, and carrageenans to improve their biological functions for potential therapeutic application","authors":"Sara El Asri ,&nbsp;Reda Ben Mrid ,&nbsp;Zakia Zouaoui ,&nbsp;Zoulfa Roussi ,&nbsp;Abdelhamid Ennoury ,&nbsp;Mohamed Nhiri ,&nbsp;Fatiha Chibi","doi":"10.1016/j.carres.2024.109358","DOIUrl":"10.1016/j.carres.2024.109358","url":null,"abstract":"<div><div>Marine sulfated polysaccharides constitute a class of bioactive polymers commonly found in cell walls of macroalgae. Among these macromolecular substances, fucoidans, ulvans, and carrageenans have attracted considerable attention providing interesting therapeutic properties affected by a combination of various structural factors, such as sulfation pattern, molecular weight, monosaccharide composition, and glycosidic linkages. Remarkably, chemical modification, enzymatic hydrolysis and crosslinking are promising approaches for developing the application of these polysaccharides through enhancement and/or addition of new biological properties. This paper reviews the recent advances on these structure modification methods on fucoidans, ulvans, and carrageenans. The physical, chemical and biological properties influenced by the addition of functional groups are also discussed. In addition, an overview of specific enzymes selectively producing oligosaccharides with improved bioactivities as well as ionic and covalent cross-linking strategies are provided. These targeted methods have the potential to develop novel compounds with outstanding biodegradability and biocompatibility, along with low toxicity suitable for diverse applications in biomedical fields, including drug delivery.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"Article 109358"},"PeriodicalIF":2.4,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142881434","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":"Unveiling cyclodextrin conjugation as multidentate excipients: An exploratory journey across industries","authors":"Roshani Gandhi ,&nbsp;Nishant Chopade ,&nbsp;Prashant K. Deshmukh ,&nbsp;Rahul G. Ingle ,&nbsp;Minal Harde ,&nbsp;Sameer Lakade ,&nbsp;Mahesh P. More ,&nbsp;Rahul S. Tade ,&nbsp;Mahesh S. Bhadane","doi":"10.1016/j.carres.2024.109357","DOIUrl":"10.1016/j.carres.2024.109357","url":null,"abstract":"<div><div>The discovery of branched molecules like dextrin by Schardinger in 1903 marked the inception of cyclodextrin (CD) utilization, catalyzing its journey from laboratory experimentation to widespread commercialization within the pharmaceutical industry. CD, a cyclic oligosaccharide containing glucopyranose units, acts as a versatile guest molecule, forming inclusion complexes (ICs) with various host molecules. Computational studies have become instrumental in elucidating the intricate interactions between β-CD and guest molecules, enabling the prediction of binding energy, forces, affinity, and complex stability. The computational approach has established robust correlations with experimental outcomes, enhancing our understanding of CD-mediated complexation phenomena. This comprehensive review delves into the CD based Inclusion complex (CDIC) formation and a myriad of components, including drug molecules, amino acids, vitamins, and volatile oils. These complexes find applications across diverse industries, ranging from pharmaceuticals to nutraceuticals, food, fragrance, and beyond. In the pharmaceutical realm, β- CDICs offer innovative solutions for enhancing drug solubility, stability, and bioavailability, thus overcoming formulation challenges associated with poorly water-soluble drugs. Furthermore, the versatility of CDs extends beyond pharmaceuticals, with applications in the encapsulation of phytoactive compounds in nutraceuticals and the enhancing flavor, aroma in food and fragrance industries. This review underscores the pivotal role of CDs conjugation in modern drug delivery systems, emphasizing the importance of interdisciplinary approaches that integrate computational modeling with experimental validation. As the pharmaceutical landscape continues to evolve, CDs-based formulations stand poised to drive innovation and address the ever-growing demand for efficacious and patient-friendly drug delivery solutions.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"Article 109357"},"PeriodicalIF":2.4,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142871485","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":"Hydroxyl groups introducing NMR strategy for structural elucidation of a heptasaccharide isolated from Trillium tschonoskii","authors":"Juan Song ,&nbsp;Guangzhong Tu ,&nbsp;Yue Liu ,&nbsp;Si Liu ,&nbsp;Yuting Zhang ,&nbsp;Wenxi Yang ,&nbsp;Xu Pang ,&nbsp;Xiaojuan Chen ,&nbsp;Haizhen Liang ,&nbsp;Jie Zhang ,&nbsp;Baiping Ma","doi":"10.1016/j.carres.2024.109359","DOIUrl":"10.1016/j.carres.2024.109359","url":null,"abstract":"<div><div>A heptasaccharide was isolated from an active fraction of <em>Trillium tschonoskii</em> using HILIC and high-temperature PGC chromatography methods. UHPLC-Q/TOF-MS analysis gave this oligosaccharide a degree of polymerization (DP) of 7 and MS/MS showed that it has a six-carbon aldehyde glucan structure with the possible chain 1 → 4 connected. The structure was determined by series 1D and 2D NMR in two solvents D₂O and DMSO‑<em>d</em>₆. Using ¹H resonances of the –OH groups as the starting point and HSQC-TOCSY on the covalent structure definition for structural elucidation allowed this heptasaccharide to be uncovered. This heptasaccharide was elucidated as maltoheptaose via complete assignment of ¹H and ¹³C with jigsaw H–C–OH pieces produced by HSQC-TOCSY at increasing mixing time. The significance of identifying maltoheptaose in <em>Trillium tschonoskii</em> indicates the high potential of –OH introducing strategy for other oligosaccharides' structural determination with relatively higher DP.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"Article 109359"},"PeriodicalIF":2.4,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142876341","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":"Recent advances in chemical synthesis of phosphodiester linkages found in fungal mannans","authors":"Zuchao Ma ,&nbsp;Harry E. Ensley ,&nbsp;Douglas W. Lowman ,&nbsp;Michael D. Kruppa ,&nbsp;David L. Williams","doi":"10.1016/j.carres.2024.109325","DOIUrl":"10.1016/j.carres.2024.109325","url":null,"abstract":"<div><div>Fungal mannans are located on the exterior of the fungal cell wall, where they interact with the environment and, ultimately, the human host. Mannans play a major role in shaping the innate immune response to fungal pathogens. Understanding the phosphodiester linkage and mannosyl repeat units in the acid-labile portion of mannans is crucial for comprehending their structure/activity relationships and for development of anti-fungal vaccines and immunomodulators. The phosphodiester linkages connect the acid-stable and acid-labile portions of the mannan polymer. Phosphate groups are attached to positions 4 and/or 6 of mannosyl repeat units in the acid-stable portion and to position 1 of mannosyl repeat units in the acid-labile portion. This review focuses on the synthesis of phosphodiester linkages as an approach to the development of mannan glycomimetics, which are based on natural product fungal mannans. Development of successful synthetic strategies for the phosphodiester linkages may enable the production of mannan glycomimetics that elicit anti-fungal immune responses against existing and emerging fungal pathogens, such as <em>Candida albicans</em> and <em>Candida auris</em>.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"547 ","pages":"Article 109325"},"PeriodicalIF":2.4,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142722419","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Chemical extension and glycodendrimer formation of the matriglycan decasaccharide, -(3Xylα1-3GlcAβ1)5- and its affinity for laminin","authors":"Kota Kotera ,&nbsp;Ren Miyamoto ,&nbsp;Gakuto Mochizuki ,&nbsp;Takahiro Tamura ,&nbsp;Noriyoshi Manabe ,&nbsp;Yoshiki Yamaguchi ,&nbsp;Jun-ichi Tamura","doi":"10.1016/j.carres.2024.109328","DOIUrl":"10.1016/j.carres.2024.109328","url":null,"abstract":"<div><div>Muscle tissue is stabilized by the strong interaction between laminin and matriglycan. Matriglycan is a polysaccharide composed of the repeating disaccharide, -3Xylα1-3GlcAβ1-, and is a pivotal part of the core M3 <em>O</em>-mannosyl glycan. Patients with muscular dystrophy cannot synthesize matriglycan or the core M3 <em>O</em>-mannosyl glycan due to a defect in or the lack of glycosyltransferases owing to glycan synthesis. Therefore, a supply of matriglycan may be a powerful tool for reconstructing muscle tissue in these patients. We herein report the synthesis of a matriglycan-repeating decasaccharide and a dendrimer comprising three branches of the decasaccharide. The glycan was regio- and stereoselectively synthesized by the stepwise addition of the corresponding disaccharide unit. The immobilized decasaccharide and glycodendrimer bound to laminin-G-like domains 4 and 5 of laminin-α2. The dissociation constants of the decasaccharide and dendrimer obtained from bio-layer interferometry were estimated to be 4.4 × 10⁻⁸ M and 6.8 × 10⁻⁸ M, respectively, showing higher affinity than those of a matriglycan-repeating hexasaccharide (1.6 × 10⁻⁷ M) and the dendrimer (1.8 × 10⁻⁷ M).</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"547 ","pages":"Article 109328"},"PeriodicalIF":2.4,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142702510","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":"Synthesis of a heptasaccharide N-glycan comprising two mannose-6-phosphate residues","authors":"Nozomi Ishii ,&nbsp;Andrea Mascherpa ,&nbsp;Antony J. Fairbanks","doi":"10.1016/j.carres.2024.109327","DOIUrl":"10.1016/j.carres.2024.109327","url":null,"abstract":"<div><div>A deprotected biantennary high mannose heptasaccharide <em>N</em>-glycan comprising two mannose-6-phosphate residues was synthesised as a putative ligand for the mannose 6-phosphate receptors, using a convergent [3 + 4] glycosylation strategy.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"547 ","pages":"Article 109327"},"PeriodicalIF":2.4,"publicationDate":"2024-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142702509","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}