Guijun Wang, Surya B. Adhikari, Pramod Aryal, Ifeanyi Okafor, Anji Chen, Anna Duffney
{"title":"Synthesis and characterization of coumarin containing fluorescent sugar based gelators","authors":"Guijun Wang, Surya B. Adhikari, Pramod Aryal, Ifeanyi Okafor, Anji Chen, Anna Duffney","doi":"10.1016/j.carres.2025.109526","DOIUrl":"10.1016/j.carres.2025.109526","url":null,"abstract":"<div><div>Carbohydrate based self-assembling systems containing coumarin functional groups are interesting class of materials. The unique fluorescence properties can be useful for many practical applications especially as biological probes. Coumarin containing low molecular weight gelators are especially interesting compounds with great potentials for new advanced molecular systems with multiple functions. We have synthesized and characterized a series of eleven coumarin based glucose and glucosamine derivatives. The structures of these compounds are based on the existing good performing supramolecular gelators through rational designs. These include three coumarin derivatives linked to anomeric positons of per-acetylated D-glucose and D-glucosamine via 1,2,3-triazole linkage , and eight4,6-benzylidene acetal protected D-glucosamine derivatives with various coumarin moieties attached to the C-2 positions through several different linkers. The gelation properties and fluorescence properties of these novel coumarin derivatives are studied and several self-assembling coumarin derivatives are also molecular gelators, which may have wide range of applications.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"554 ","pages":"Article 109526"},"PeriodicalIF":2.4,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144124568","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}
Raju R. Kale , Nitin K. Jadhav , Sanchayita Rajkhowa , Bhausaheb B. Muntode , Vikram A. Dhere , Nitin D. Gaikwad , Vaishali S. Shinde
{"title":"Recent advances in synthesis of carbohydrate-based surfactants: Comprehensive review and future perspective","authors":"Raju R. Kale , Nitin K. Jadhav , Sanchayita Rajkhowa , Bhausaheb B. Muntode , Vikram A. Dhere , Nitin D. Gaikwad , Vaishali S. Shinde","doi":"10.1016/j.carres.2025.109521","DOIUrl":"10.1016/j.carres.2025.109521","url":null,"abstract":"<div><div>This review aims to explore the rapid development of carbohydrate-based surfactants (CBS) as sustainable, biocompatible, and eco-friendly alternatives to conventional petrochemical-derived surfactants. It aims to assess how CBS, derived from renewable resources, are redefining the landscape of surfactant technologies in the context of increasing global demand for environmentally responsible materials. The review presents a comprehensive analysis of recent innovations in the synthesis of CBS, focusing on strategies that utilize abundant carbohydrate-rich feedstocks such as cellulose, pectin, hemicellulose, and starch. It discusses the physicochemical principles underlying CBS design and examines current synthesis approaches, structural modifications, and functional performance trends. The findings highlight that the unique amphiphilic nature of CBS facilitates the formation of stable emulsions, micelles, and other self-assembled systems critical for industrial and biomedical applications. These advances demonstrate CBS's growing utility and versatility and underscore their potential as green, multifunctional materials poised to play a significant role in future sustainable technologies. This review concisely delves into the most recent synthetic developments in carbohydrate-based surfactants (CBS), particularly emphasizing molecular design strategies that exploit the inherent structural diversity and functionality of renewable carbohydrate feedstocks and also highlights emerging structure-function paradigms and delineates future directions for scalable, bio-based surfactant design in industrial and biomedical sectors.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"554 ","pages":"Article 109521"},"PeriodicalIF":2.4,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144090504","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":"Simultaneous one-pot multienzymatic synthesis and purification of Uridine-5′-Diphosphate-α-D-glucuronide and Uridine-5′-Diphosphate-α-d-xylose","authors":"Arnaud Pâris, Tiffany Rundstadler , Pierre Lafite","doi":"10.1016/j.carres.2025.109516","DOIUrl":"10.1016/j.carres.2025.109516","url":null,"abstract":"<div><div>Glucuronosyltransferases and xylosyltransferases are glycosyltransferases (GT) that are involved in a wide range of biological processes, including xenobiotic metabolism or proteoglycan biosynthesis and require as substrates activated sugar donors, respectively UDP-α-D-glucuronide (UDP-GlcA) and UDP-α-<span>d</span>-xylose (UDP-Xyl). As both nucleotide sugars are hardly available, we have developed a one-pot multienzymatic synthesis to produce sequentially UDP-GlcA and UDP-Xyl. This methodology involves the production of UDP-GlcA for glucuronic acid, coupling glucuronokinase and UDP-sugar pyrophosphorylase activities, followed by UDP-GlcA decarboxylation by UDP-Xylose Synthase. Each of these UDP-sugars can then be simultaneously purified and isolated from the unique reaction mixture, providing an efficient production methodology of these rare UDP-sugars for subsequent enzymatic studies of corresponding GT.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"554 ","pages":"Article 109516"},"PeriodicalIF":2.4,"publicationDate":"2025-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144072249","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":"Building block approach for the convenient synthesis of resorcinol alkyl C-glucoside","authors":"Amudala Subramanyam, Sumit, Indrapal Singh Aidhen","doi":"10.1016/j.carres.2025.109522","DOIUrl":"10.1016/j.carres.2025.109522","url":null,"abstract":"<div><div>Structural modifications with natural phenylbutyl glucosides have revealed the importance of oxygenation pattern in the aryl residue and the spacer length towards the tyrosinase inhibition activity. The tetradecyl spaced <em>O</em>-glucoside resorcinol derivative being about 27 times more potent than kojic acid and exceeds the effectiveness of 4-hexylresorcinol as tyrosinase inhibitor. We have developed the first synthetic route for the <em>C</em>-analogue with tetradecyl alkyl spacer between the resorcinol aryl ring and <span>d</span>-glucosyl residue. The synthesis has been achieved using the Julia-Kocienski olefination reaction for C–C bond formation. The sulfone building blocks used herein would allow synthesis of various analogues with different chain lengths and functionalities.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"553 ","pages":"Article 109522"},"PeriodicalIF":2.4,"publicationDate":"2025-05-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143947129","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}
Lawrence Webb , Stephen R. Graves , John Stenos , Karren M. Plain , Xavier A. Conlan
{"title":"Detection of the unique sugars virenose and dihydrohydroxystreptose from Coxiella burnetii using alditol acetylation and liquid chromatography mass spectroscopy","authors":"Lawrence Webb , Stephen R. Graves , John Stenos , Karren M. Plain , Xavier A. Conlan","doi":"10.1016/j.carres.2025.109524","DOIUrl":"10.1016/j.carres.2025.109524","url":null,"abstract":"<div><div>The bacterium <em>Coxiella burnetii</em> causes Q-Fever in humans and coxiellosis in animals. This work presents a robust, sensitive and selective method for the identification of two unique sugars found in the lipopolysaccharide of <em>C. burnetii</em>. The sugars were derivatised using alditol acetylation and identified using high performance liquid chromatography coupled to high resolution mass spectrometry. Virenose and dihydrohydroxystreptose were observed to be only partially acetylated during derivatisation and this was found to be valuable for the identification of these sugars in the absence of commercial standards. This sensitive methods can be applied in diagnostic fields and help to further characterise the cell-wall lipopolysaccharide of <em>C. burnetii.</em></div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"553 ","pages":"Article 109524"},"PeriodicalIF":2.4,"publicationDate":"2025-05-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143937813","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}
Jianchuan Wu, Kun Yang, Jinfan Zhou, Lincen He, Yujie Zhou, Bei Yu
{"title":"Novel polysaccharide-based fluorescent polymer drug delivery systems with natural extracts for squamous cell carcinoma treatment","authors":"Jianchuan Wu, Kun Yang, Jinfan Zhou, Lincen He, Yujie Zhou, Bei Yu","doi":"10.1016/j.carres.2025.109525","DOIUrl":"10.1016/j.carres.2025.109525","url":null,"abstract":"<div><div>This study introduces a novel synthesis method for a new coordination polymer (CP) based on N-donor and O-donor organic ligands. The polymer, with the chemical formula <strong>Co(ptda)(bib)</strong> (where <strong>H<sub>2</sub>pdta = 5'-(pyridine-2-yl)-[1,1':3′,1′-terphenyl]-4,4′-dicarboxylic acid</strong>, <strong>bib = 4,4′-bis(1-imidazolyl) biphenyl</strong>), was synthesized via solvothermal methods. The structure of the polymer was characterized using <strong>single-crystal X-ray diffraction</strong> and <strong>elemental analysis</strong>. Subsequently, a biodegradable polymer-based drug delivery system was constructed, consisting of <strong>polyvinyl alcohol (PVA)</strong> and <strong>polygalacturonic acid (PGA)</strong>, with potential biomedical applications. For this purpose, <strong>PVA-PGA</strong> was utilized as the carrier shell in the development of a drug delivery system for <strong>compound 1</strong> and <strong>Brazilin-loaded CP1</strong> (<strong>PVA-PGA@CP1@1@Brazilin</strong>). The potential of <strong>PVA-PGA@CP1@1@Brazilin</strong> as a drug delivery carrier was explored, highlighting its distinct advantages. Furthermore, <strong>in vitro cell experiments</strong> were conducted to evaluate the therapeutic efficacy of <strong>PVA-PGA@CP1@1@Brazilin</strong> in the treatment of <strong>squamous cell carcinoma (SCC)</strong>, offering a promising approach for targeted SCC therapy and providing a novel strategy for clinical development.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"554 ","pages":"Article 109525"},"PeriodicalIF":2.4,"publicationDate":"2025-05-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144070025","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":"Microwave-assisted click synthesis of levoglucosan triazolyl glycoconjugates using ascorbyl palmitate sodium salt (Asp-Na) as a green Co-catalyst","authors":"Nishant Pandey , Pratibha Dwivedi , Alisha , Bhuwan B. Mishra","doi":"10.1016/j.carres.2025.109511","DOIUrl":"10.1016/j.carres.2025.109511","url":null,"abstract":"<div><div>Ascorbyl palmitate sodium salt (Asp-Na) <strong>2</strong> has been found to be a highly effective co-catalyst in copper catalyzed azide-alkyne cycloaddition (CuAAC) reactions under microwave (MW) condition. This co-catalyst provides a more cost-efficient option compared to sodium ascorbate by reducing the stoichiometric amount of ascorbic acid required for the CuAAC reaction. With its palmitate side chain, Asp-Na <strong>2</strong> acts as a surfactant by improving the solubility of substrates, particularly the lipophilic compounds. Notably, it can be obtained in high purity by semi-synthesis from non-edible oils, aligning with the sustainable practices. Application of <strong>2</strong> in CuAAC reaction of levoglucosan based terminal alkyne <strong>(3)</strong> and <em>azido</em>-sugars <strong>(4)</strong> furnished the corresponding triazolyl glycoconjugates <strong>(5)</strong> in yields ranging between 70 and 90 %.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"553 ","pages":"Article 109511"},"PeriodicalIF":2.4,"publicationDate":"2025-05-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143943411","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":"Analysis of CD22 cis-ligands using a synthetic sialoside binding to CD22 with ultra-high affinity","authors":"Amin Alborzian Deh Sheikh , Wang Long , Naoko Matsubara , Takeshi Futamura , Akihiro Imamura , Hiromune Ando , Shiho Ohno , Hajjaj H.M. Abdu-Allah , Hiromu Takematsu , Masatake Asano , Yoshiki Yamaguchi , Hideharu Ishida , Takeshi Tsubata","doi":"10.1016/j.carres.2025.109519","DOIUrl":"10.1016/j.carres.2025.109519","url":null,"abstract":"<div><div>CD22 (also known as Siglec-2), an inhibitory receptor expressed in B lymphocytes (cells), recognizes the glycan structure α2,6-sialylated <em>N</em>-acetyllactosamine, and constitutively associates with various α2,6-sialylated membrane proteins expressed on the same cell (<em>cis</em>-ligands) although CD22 can bind to α2,6-sialylated molecules expressed in other cells (<em>trans</em>-ligands). The inhibitory activity of CD22 is regulated by the <em>cis</em>-ligands, and CD22 regulates B cells through the <em>cis</em>-ligands. Because of fast dissociation kinetics of the binding of CD22 with the ligands, systematic identification of CD22 ligands is not possible by conventional methods such as immunoprecipitation. Previously, we showed that proximity labeling using tyramide efficiently labels CD22-associated molecules. However, whether this association depends on the recognition of sialic acid by CD22 needs to be demonstrated to identify the <em>cis</em>-ligands. Here we develop the synthetic sialoside GSC-932 in which modification of the C5 position of the sialic acid core with a guanidyl group improves the affinity to mouse CD22 by 50 folds probably by generating the interaction of the guanidyl group with several amino acid residues in mouse CD22 such as E136 and R137, thereby efficiently inhibiting the binding of mouse CD22 with the α2,6-sialylated ligands. Application of GSC-932 to the proximity labeling clearly distinguishes sialic acid-dependent association with CD22 and shows that CD22 associates with a variety of <em>cis</em>-ligands. GSC-932 may be a useful tool to study ligand interaction of CD22.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"554 ","pages":"Article 109519"},"PeriodicalIF":2.4,"publicationDate":"2025-05-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144069804","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":"Multivalent Siglec ligands","authors":"Roland J. Pieters","doi":"10.1016/j.carres.2025.109520","DOIUrl":"10.1016/j.carres.2025.109520","url":null,"abstract":"<div><div>Siglecs are proteins that play important biological roles, especially in the immune system. Intervention with Siglec recognition has potential for modulation of the immune system. Progress in the discovery of specific Siglec ligands combined with the use of multivalent platforms for these ligands has allowed effective intervention in various scenarios. This review discusses these systems and focuses on the nature of these multivalent systems.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"553 ","pages":"Article 109520"},"PeriodicalIF":2.4,"publicationDate":"2025-05-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143935171","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}
Alexander C. Anderson , Tyler Malloch , Anthony J. Clarke
{"title":"From structure to function: Decoding peptidoglycan O-acetylation in pathogenic bacteria","authors":"Alexander C. Anderson , Tyler Malloch , Anthony J. Clarke","doi":"10.1016/j.carres.2025.109517","DOIUrl":"10.1016/j.carres.2025.109517","url":null,"abstract":"<div><div>Numerous pathogenic and non-pathogenic bacteria modulate the structure of their cell wall to escape the action of lytic enzymes that target it, threatening cell integrity. Of these modifications, the most taxonomically widespread is the addition of an acetyl to the C6 hydroxyl group of muramyl residues within the essential cell-wall heteropolymer peptidoglycan. This modification is found in many clinically important pathogens, including the WHO priority pathogens <em>Neisseria gonorrhoeae, Staphylococcus aureus, Enterococcus faecium,</em> and <em>Streptococcus pneumoniae</em>. In this review, we summarize the last 60 years of discoveries about the genetics, biochemistry, structural biology, and cellular metabolism that underlie this enigmatic bacterial self-defence mechanism.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"554 ","pages":"Article 109517"},"PeriodicalIF":2.4,"publicationDate":"2025-05-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144083916","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}