{"title":"Cyclodextrin-based molecules as hosts in the formation of supramolecular complexes and their practical applications—A review","authors":"R. Periasamy","doi":"10.1080/07328303.2021.1967970","DOIUrl":"10.1080/07328303.2021.1967970","url":null,"abstract":"<div><p>The excellent biocompatibility and unique inclusion capability as well as powerful functionalization capacity of cyclodextrins and their derivatives make them especially attractive for engineering novel functional materials for many applications. There has been increasing interest recently to fabricate supramolecular systems based on cyclodextrin materials. This review focuses on state-of-the-art and recent advances in the construction of cyclodextrin-based assemblies and their practical applications in many fields like gene therapy, chemotherapy, antimicrobial drug delivery, metal extraction, food industry, etc. Supramolecular self-assembly materials based on cyclodextrins are also discussed in this review. The fabrication technologies of supramolecular systems including nanoplatforms and hydrogels as well as their applications in nanomedicine and pharmaceutical sciences are highlighted. In the end, the future directions of this field are discussed.</p><p><span><figure><span><img><ol><li><span>Download : <span>Download high-res image (942KB)</span></span></li><li><span>Download : <span>Download full-size image</span></span></li></ol></span></figure></span></p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"40 4","pages":"Pages 135-155"},"PeriodicalIF":1.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48340493","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chengkai Zhou , Zhuojia Xu , Gen Li , Qi Gao , Qiang Sui , Tiehai Li
{"title":"Efficient synthesis of monophosphoryl lipid A mimetic RC-529","authors":"Chengkai Zhou , Zhuojia Xu , Gen Li , Qi Gao , Qiang Sui , Tiehai Li","doi":"10.1080/07328303.2021.2016793","DOIUrl":"10.1080/07328303.2021.2016793","url":null,"abstract":"<div><p>An efficient approach for the facile synthesis of a potent vaccine adjuvant RC-529 is described. The synthetic strategy relies on the flexible use of orthogonal protecting groups, which makes it possible to accomplish selective phosphorylation, glycosylation and acylation, respectively. In addition, the use of readily cleaved 2-naphthylmethyl (Nap) ether and allyl esters as permanent protecting groups greatly facilitates the final global deprotection steps to obtain pure RC-529. This work will contribute to the synthesis of lipid A and its derivatives.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"40 7","pages":"Pages 501-517"},"PeriodicalIF":1.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43582800","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Xuewei Jia , Xuanjing Wang , Yuanshang Liu , Yiyan Sun , Bingjie Ma , Zhenjie Li , Chunping Xu
{"title":"Structural characterization of an alkali-extracted polysaccharide from Dioscorea opposita Thunb. with initial studies on its anti-inflammatory activity","authors":"Xuewei Jia , Xuanjing Wang , Yuanshang Liu , Yiyan Sun , Bingjie Ma , Zhenjie Li , Chunping Xu","doi":"10.1080/07328303.2021.2009503","DOIUrl":"10.1080/07328303.2021.2009503","url":null,"abstract":"<div><p>An alkali-extracted polysaccharide (HY-B) was isolated and purified from <em>Dioscorea opposita</em> Thunb. (Huai Yam). Its chemical structure was analyzed with FT-IR, GC-MS and 1 D, 2 D-NMR spectrometry. It was proved that HY-B is mainly composed of α-1,4-linked glucose, which is similar to starch, but the starch-iodine color test proved that it was not starch. The chain conformation of HY-B was analyzed by SEC-MALLS-RI and TEM, indicated that HY-B exists in a random coil conformation. Its molecular weight is 18.7 kDa, and the molecular size is about 100 nm. MTT assays indicated that HY-B was nontoxic to RAW 264.7 cells <em>in vitro</em>. The results of anti-inflammatory studies showed that HY-B could inhibit the production of NO and TNF-α in RAW 264.7 macrophage stimulated by lipopolysaccharides (LPSs). This work provided the important information about the anti-inflammatory active component of Huai Yam and its potential applications in the food and health industries.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"40 6","pages":"Pages 308-324"},"PeriodicalIF":1.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43754942","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Practical synthesis of 2-deoxy sugars via metal free deiodination reactions","authors":"Wang Yao , Hao Wang , Jing Zeng , Qian Wan","doi":"10.1080/07328303.2021.2015365","DOIUrl":"10.1080/07328303.2021.2015365","url":null,"abstract":"<div><p>2-Deoxy-glycosides, in which the C-2 hydroxyl group is replaced with a hydrogen atom, are important motifs in numerous bioactive natural products and pharmaceutical molecules. Herein, an improved dilauroyl peroxide-mediated radical deiodination reaction by using cyclohexane and ethyl acetate as co-solvent is reported. This is an environmentally benign protocol, which operates smoothly under mild conditions and allows efficient preparation of a series of 2-deoxy-glycosides in up to 98% yields.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"40 7","pages":"Pages 454-478"},"PeriodicalIF":1.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42567946","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Comparative study of binding abilities of Siglec-7 to different ligands using molecular modeling techniques and structural analysis","authors":"Madhumita Dandopath Patra","doi":"10.1080/07328303.2021.1954656","DOIUrl":"10.1080/07328303.2021.1954656","url":null,"abstract":"<div><p>Sialic acid binding Ig-like lectins (siglecs) are type I membrane proteins characterized by their sequence similarity and ability to bind sialic acid moieties in glycoproteins and glycolipids. Siglecs can regulate the functions of cells in the innate and adaptive immune systems and promote cell–cell interactions through glycan recognition. Siglec-7, a member of the siglec family, is expressed on NK cells and displays unique ligand binding properties different from the other member of the Siglec family. Siglec-7 prefers α(2,8)-disialyl group and branched α(2,6)-sialyl group containing ligands. In this paper, complexes of Siglec-7 in solution with α(2,8)-disialyl group containing ligand GD3, branched α(2,6)-sialyl group containing ligand LSTb and α(2,6)-sialyl group containing ligand LSTc have been modeled based on the crystal structure of Siglec7-DSLc4[α(2,3)/α(2,6)-disialyl lactotetraosyl 2-(trimethylsilyl)ethyl] complex. Structural analysis of these complexes and calculation of theoretical dissociation constant values helped to conclude that GD3 and LSTb can form better complex with Siglec7 than LSTc in solution and all the ligands, DSLc4, GD3, LSTb, and LSTc can form better complexes in solution than in the crystal structure.</p><p><span><figure><span><img><ol><li><span>Download : <span>Download high-res image (214KB)</span></span></li><li><span>Download : <span>Download full-size image</span></span></li></ol></span></figure></span></p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"40 4","pages":"Pages 179-196"},"PeriodicalIF":1.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2021.1954656","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41891360","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthetic linear glycopolymers and their biological applications","authors":"Qian Qin , Shuyao Lang , Xuefei Huang","doi":"10.1080/07328303.2021.1928156","DOIUrl":"10.1080/07328303.2021.1928156","url":null,"abstract":"<div><p>As typical affinities of carbohydrates with their receptors are modest, polymers of carbohydrates (glycopolymers) are exciting tools to probe the multifaceted biological activities of glycans. In this review, the linear glycopolymers and the multivalency effects are first introduced. This is followed by discussions of methods to synthesize these polymers. Subsequently, the interactions of glycopolymers with plant lectins and viral/bacterial carbohydrate binding proteins are discussed. In addition, applications of the glycopolymers in facilitating glycan microarray studies, mimicking cell surface glycans, modulation of the immune system, cryoprotection of protein, and electron-beam lithography are presented to stimulate further development of this fascinating technology.</p></div><div><h3>Graphical Abstract</h3><p><span><figure><span><img><ol><li><span>Download : <span>Download high-res image (74KB)</span></span></li><li><span>Download : <span>Download full-size image</span></span></li></ol></span></figure></span></p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"40 1","pages":"Pages 1-44"},"PeriodicalIF":1.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2021.1928156","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47455558","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Glycogen synthesis from dihydroxyacetone in isolated rat hepatocytes","authors":"Mireia Díaz-Lobo , Josep Maria Fernández-Novell","doi":"10.1080/07328303.2021.1955129","DOIUrl":"10.1080/07328303.2021.1955129","url":null,"abstract":"<div><p>Glycogenolysis and gluconeogenesis are sensitive to nutritional state and their balances are disrupted in the liver by different pathological states. The regulation of the balance between glucose production and synthesis of glycogen continues to be a matter of investigation because of its implications in diseases and its value for therapeutics. We used the gluconeogenic precursor dihydroxyacetone (DHA) to study glycogen synthesis in isolated rat hepatocytes under gluconeogenic conditions. We used a glycogen phosphorylase (GP) inhibitor, 2-deoxy-2-fluoro-α-D-glucopyranosyl fluoride (F<sub>2</sub>Glc) to prevented GP from breaking up glycogen into glucose subunits and had a pool of glucose in the medium. Therefore, we evaluated the contribution of DHA as a unique source of carbohydrates on glycogen metabolism. We showed that DHA increased G6P levels that induced both GS activation and its translocation and, thus, an increment of glycogen deposition in a similar way as glucose did.</p><p><span><figure><span><img><ol><li><span>Download : <span>Download high-res image (417KB)</span></span></li><li><span>Download : <span>Download full-size image</span></span></li></ol></span></figure></span></p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"40 4","pages":"Pages 197-210"},"PeriodicalIF":1.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2021.1955129","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48171620","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Recent development in additive modulated stereoselective glycosidation reactions","authors":"Miaomiao Zhang , Tianlu Li , Peng Peng","doi":"10.1080/07328303.2022.2027432","DOIUrl":"10.1080/07328303.2022.2027432","url":null,"abstract":"<div><p>Stereoselective glycosidic bond formation (termed “glycosidation”) remains a challenge in carbohydrate chemistry. Despite such difficulty, a variety of innovative strategies have been developed. In particular, additive-modulated stereoselective construction of glycosidic linkages has become an emerging trend. In this review, we summarized the recent progress in this area with respect to common glycosyl donors, including thioglycosides, glycosyl imidates, glycosyl acetates, glycosyl hemiacetals, glycosyl phosphates and glycosyl ortho-alkynylbenzoates. Together with their merits/limitations, these achievements shed light on carbohydrate chemistry and enabled the efficient preparation of complex oligosaccharides and glycoconjugates.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"40 7","pages":"Pages 339-360"},"PeriodicalIF":1.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46529535","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"2020 T. Ogawa Young Investigator Award","authors":"Zhongwu Guo","doi":"10.1080/07328303.2021.2015367","DOIUrl":"10.1080/07328303.2021.2015367","url":null,"abstract":"I am delighted to announce that the winners of the 2020 T. Ogawa Young Investigator Award are Professor Jian Yin from the Key Laboratory of Carbohydrate Chemistry and Biotechnology, Jiangnan University, China and Professor Zhimeng Wu from the Key Laboratory of Carbohydrate Chemistry and Biotechnology, Jiangnan University, China, respectively. T. Ogawa Young Investigator Award has been established by the Journal of Carbohydrate Chemistry and is given annually to recognize young principal investigators for their excellent contributions to carbohydrate chemistry.","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"40 6","pages":"Page 325"},"PeriodicalIF":1.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46002876","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"One-pot iterative glycosylations toward a tetrasaccharide related to the O-specific polysaccharide from Escherichia coli O132","authors":"Vijay Nath Mishra , Pintu Kumar Mandal","doi":"10.1080/07328303.2021.1928153","DOIUrl":"10.1080/07328303.2021.1928153","url":null,"abstract":"<div><p>An efficient synthetic strategy has been developed for the synthesis of a tetrasaccharide related to the <em>O</em>-specific polysaccharide from <em>Escherichia coli</em> O132 as their 2-aminoethyl glycosides in a very good yield by adopting sequential glycosylation followed by <em>in-situ</em> removal of the <em>p</em>-methoxybenzyl (PMB) group in the same reaction pot. Furthermore, the synthetic route was adapted by carrying out three stereoselective iterative glycosylations followed by in situ removal of the PMB group in one pot. The stereochemical outcomes of all the glycosylation steps were excellent with satisfactory yields.</p></div><div><h3>Graphical Abstract</h3><p><span><figure><span><img><ol><li><span>Download : <span>Download high-res image (198KB)</span></span></li><li><span>Download : <span>Download full-size image</span></span></li></ol></span></figure></span></p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"40 1","pages":"Pages 66-82"},"PeriodicalIF":1.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2021.1928153","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48155424","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}