Min Jiang , Jie Zhao , Guodong Mei , Han Lin , Haofei Hong , Dan Li , Zhimeng Wu
{"title":"Chemoenzymatic synthesis of 6′-sialolactose-modified nanobody","authors":"Min Jiang , Jie Zhao , Guodong Mei , Han Lin , Haofei Hong , Dan Li , Zhimeng Wu","doi":"10.1080/07328303.2022.2055048","DOIUrl":"10.1080/07328303.2022.2055048","url":null,"abstract":"<div><p>6′-Sialolactose-modified mono- and bivalent nanobodies were designed and synthesized by a chemoenzymatic strategy. Epidermal growth factor receptor (EGFR)-targeting 7D12 nanobodies, including mono- and bivalent 7D12, were recombinantly expressed in <em>Escherichia coli</em>. Triglycine-modified 6′-sialolactose derivative was synthesized in nine steps. The conjugation of carbohydrates with nanobodies was achieved by Sortase-A mediated ligation with high conversion rates. The obtained glycoengineered nanobodies were finally verified by SDS-PAGE, western blot, and mass spectrometry.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"41 2","pages":"Pages 207-221"},"PeriodicalIF":1.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44591466","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":"Facile synthesis of novel 3H-1,5-benzodiazepine-derived aryl C-glycosides by coupling of sugar alkynes, acyl chlorides and 1, 2-phenylenediamine","authors":"Qianxia Chen , Xiang Zhou , Fen Han , Fuyi Zhang , Yufen Zhao","doi":"10.1080/07328303.2022.2045020","DOIUrl":"10.1080/07328303.2022.2045020","url":null,"abstract":"<div><p>Novel 3<em>H</em>-1,5-benzodiazepine-derived aryl <em>C</em>-glycosides were synthesized in good to excellent yields by the coupling of structurally diverse terminal sugar alkynes, aroyl chlorides and 1, 2-phenylenediamine. The protocol is general, mild and efficient. It was suitable for various terminal sugar alkynes and aroyl chlorides, with 37 selected examples. The sugar substrates include pyranosides, furanosides, and acyclic sugars with sensitive and bulky protecting groups. The aroyl chlorides contain electron-donating, electron-withdrawing and electron-neutral substituents.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"41 1","pages":"Pages 28-50"},"PeriodicalIF":1.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46535329","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}
Xiaoming Wen , Jian Wang , Luan He , Bisheng Wei , Ying Xie
{"title":"Synthesis of glucopyranoside benzimidazolium-based ionic liquids for Pd-catalyzed aqueous Suzuki reaction","authors":"Xiaoming Wen , Jian Wang , Luan He , Bisheng Wei , Ying Xie","doi":"10.1080/07328303.2022.2141770","DOIUrl":"10.1080/07328303.2022.2141770","url":null,"abstract":"<div><p>Several novel benzimidazolium-based ionic liquids (BzIm ILs) with free and acetyl protected glucopyranoside unit were synthesized and used as ligand for Pd-catalyzed environment-friendly Suzuki reaction. The BzIm ILs with the acetyl protection shows the highest activity, probably because the sugar has a large steric hindrance and acetyl groups can coordinate with Pd. The nuclear magnetic resonance spectra of Pd(OAc)<sub>2</sub>/Glc-BzIm ILs free glucopyranoside indicate that Pd-C is formed. The Pd nanoparticles protected by ILs with a size of 5.3 (0.6) nm are considered to be real active species. A series of fluorene core arylfluorene derivatives were prepared with isolated yields above 90%.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"41 6","pages":"Pages 369-384"},"PeriodicalIF":1.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46696689","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}
Porkodi Kadhirvel , Manuel Azenha , Galya Ivanova , Carlos Pereira , António F. Silva
{"title":"A simpler and greener alternative route for anchoring carbohydrates with structural integrity on silica and glass supports","authors":"Porkodi Kadhirvel , Manuel Azenha , Galya Ivanova , Carlos Pereira , António F. Silva","doi":"10.1080/07328303.2022.2121835","DOIUrl":"10.1080/07328303.2022.2121835","url":null,"abstract":"<div><p>A novel, straightforward, and environmentally friendly direct coupling procedure to immobilize carbohydrates on solid supports is presented. A characterization study showed that all amino groups on solid supports participated in the linkage with a carbohydrate unit, implicating that the surface load can be easily adjusted by tuning the amination coverage of the surface. Most importantly, the integrity of the cyclic conformation of the linked sugar unit was demonstrated, a feature that is critical for most of the possible applications of carbohydrate-functionalized surfaces. Furthermore, carbohydrate-immobilized submicron particles synthesized by the direct coupling method, on which lectin profiling experiments were conducted, validated the successfulness of our simplistic approach.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"41 6","pages":"Pages 346-368"},"PeriodicalIF":1.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44167036","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":"Structural and conformational dynamics of human milk oligosaccharides, lacto-N-fucopentaose I and II, through molecular dynamics simulation","authors":"B. Lalithamaheswari , C. Anu Radha","doi":"10.1080/07328303.2022.2150203","DOIUrl":"10.1080/07328303.2022.2150203","url":null,"abstract":"<div><p>Carbohydrates, also known as glycans or sugars are the nature’s most abundant biomolecules. Human breast milk contains soluble oligosaccharides that are involved in the biological recognition process. Oligosaccharides occur in numerous conformational states due to their flexible nature at glycosidic linkages. Molecular dynamics simulation is used to investigate the structural flexibility of glycosidic linkage and intramolecular interactions between molecules. The work focused on human milk oligosaccharide (HMOs), lacto-<em>N</em>-fucopentaose (LNFP) I and II, investigated through MD simulation for 250 ns, and its replicate. Possible conformational models for LNFP I and II were determined and deposited in the open-access database 3DSDSCAR. The structural analysis was carried out for the two HMOs with the CPPTRAJ module.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"41 6","pages":"Pages 385-404"},"PeriodicalIF":1.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44579781","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}
Yi-Xuan Li , Bo-Wen Lu , Si-Liang Jiang , Cai-Xia Dong , Juan Du
{"title":"Structural characterization of water-soluble polysaccharides from Sophora flavescens Ait. and their anti-inflammatory activities based on NO release","authors":"Yi-Xuan Li , Bo-Wen Lu , Si-Liang Jiang , Cai-Xia Dong , Juan Du","doi":"10.1080/07328303.2023.2174551","DOIUrl":"10.1080/07328303.2023.2174551","url":null,"abstract":"<div><p><em>Sophora flavescens</em> Ait. is a medicinal herb traditionally used to treat inflammatory diseases. In this study, four polysaccharides, SFNP-1, SFNP-2, SFAP-1, and SFAP-2, were isolated from <em>S. flavescens</em>. Both SFNP-1 and SFNP-2 were (1→4)-linked glucans. SFAP-1 and SFAP-2 were identified as pectin-type polysaccharides containing mainly a homo-galacturanan backbone (as shown). NO release inhibition test revealed that the major polysaccharides, SFAP-1 and SFAP-2, did not have a significant anti-inflammatory effect. This result suggests that the anti-inflammatory effect of <em>S. flavescens</em> may not depend on its polysaccharides.</p><p><span><figure><span><img><ol><li><span>Download : <span>Download high-res image (12KB)</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":"41 7","pages":"Pages 405-423"},"PeriodicalIF":1.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41906399","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}
Mohammed Jabedul Hoque , Mitsuo Toda , Nobuyuki Mase
{"title":"Comparative study of inclusion complex formation between β-cyclodextrin (host) and aromatic diamines (guests) by mixing in hot water, co-precipitation, and solid-state grinding methods","authors":"Mohammed Jabedul Hoque , Mitsuo Toda , Nobuyuki Mase","doi":"10.1080/07328303.2022.2068026","DOIUrl":"10.1080/07328303.2022.2068026","url":null,"abstract":"<div><p>Aromatic diamines are essential components of polyimide and many other thermosetting polymers. Recent attention has been growing on the threading of cyclodextrins (CDs) onto diamine monomers intended to improve the solubility in water and thermal stability of resultant polymers. The co-precipitation method is often used to isolate inclusion complexes (ICs) of aromatic diamines and other sparingly water-soluble aromatic guest molecules with β-CD. To find the viability of other methods, we studied IC formation between β-CD and some aromatic diamines by mixing in hot water, co-precipitation, and solid-state grinding. ICs formation in water was carried out by solid guest dispersion into the β-CD aqueous solution at 80<!--> <!-->°C with high-speed magnetic stirring. In contrast, solid-state grinding was employed by adding a small amount of water to promote IC formation. Thus, ICs prepared by mixing in hot water and solid-state grinding methods were crystallized from water by cooling to 4 °C. Structures of the ICs in solution were confirmed by chemical shifts changes of cavity protons of β-CD in <sup>1</sup>H NMR and the cross-peaks between aromatic protons and cavity protons in <sup>1</sup>H-<sup>1</sup>H ROESY NMR. Job’s plot and NMR titration experiments were used to determine the stoichiometric ratio of host and guest in solution.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"41 4","pages":"Pages 249-272"},"PeriodicalIF":1.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44528827","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}
Grazia Isa. C. Righetti , Ada Truscello , Jiemeng Li , Roberto Sebastiano , Attilio Citterio , Cristian Gambarotti
{"title":"Sustainable synthesis of zwitterionic galactaric acid monoamides as monomers of hydroxylated polyamides","authors":"Grazia Isa. C. Righetti , Ada Truscello , Jiemeng Li , Roberto Sebastiano , Attilio Citterio , Cristian Gambarotti","doi":"10.1080/07328303.2022.2105861","DOIUrl":"10.1080/07328303.2022.2105861","url":null,"abstract":"<div><p>A new and sustainable preparation of zwitterionic monoamides of galactaric acid is reported. The protocol consists of an efficient conversion of aldaric acid into the corresponding lactone and its further reaction in the presence of diamines, leading to the formation of the corresponding zwitterionic monoamides in high yields and selectivity. The zwitterions have been used as monomers to obtain the corresponding polyhydroxyamides. The overall protocol has shown a high atom economy, and all the carbon atoms present in the reagents are preserved.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"41 5","pages":"Pages 314-328"},"PeriodicalIF":1.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43130250","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":"Cationic gold(I)-catalyzed glycosylation with glycosyl S-3-butynyl thiocarbonate donors","authors":"Prakash Thapa , Prem Bahadur Gurung , Ishani Lakshika Hettiarachchi , Jianglong Zhu","doi":"10.1080/07328303.2022.2076863","DOIUrl":"10.1080/07328303.2022.2076863","url":null,"abstract":"<div><p>A cationic gold(I)-catalyzed <em>O</em>-glycosylation method involving the use of glycosyl <em>S</em>-3-butynyl thiocarbonate donors has been developed. It was found that glycosyl <em>S</em>-3-butynyl thiocarbonates are orthogonal to regular phenyl thioglycoside donors. The utilization of this method was demonstrated in the synthesis of a trisaccharide.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"41 4","pages":"Pages 223-237"},"PeriodicalIF":1.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42564970","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":"The features of liver glycogen fractions in streptozotocin-induced type-I diabetic rats","authors":"Kousar Daneshnia , Mani Nosrati , Zahra Bakouei-Katrimi , Mehdi Rasouli","doi":"10.1080/07328303.2022.2068027","DOIUrl":"10.1080/07328303.2022.2068027","url":null,"abstract":"<div><p>The ratio of counter-regulatory hormones to insulin is increased in diabetes. This causes a change in the activities of the enzymes involved in glycogen metabolism. Thus, it is expected that the structure of glycogen will be changed reversibly in diabetes mellitus. The current research was done to study whether the fractions of glycogen have been changed in streptozotocin (STZ)-induced diabetes in rats. To this end, one group of 10 male rats received a single injection with STZ and were compared with the control group. Liver glycogen fractions were analyzed for the content of carbohydrates, protein, and organic phosphate. Hyperglycemia and clinical signs of diabetes appeared after two days of STZ- injection and continued up to two weeks. In diabetic rats relative to controls, total glycogen decreased by about 39% (24.4<!--> <!-->±<!--> <!-->3.0 mg/g wet weight of liver <em>vs.</em> 39.7 ± 2.2, <em>p</em> = 0.001), and the change happened entirely in acid-soluble glycogen (ASG) fraction (19.1<!--> <!-->±<!--> <!-->1.7 <em>vs.</em> 33.4 ± 2.2, <em>p</em> = 0.001), while acid-insoluble glycogen (AIG) increased slightly but not significantly (5.5 ± 1.1, <em>vs.</em> 4.5 ± 0.8, <em>p</em> = 0.5). Diabetes was also associated with the change in the content of glycogen protein and the ratio of ASG to AIG. The content of organic phosphate was 181.4<!--> <!-->±<!--> <!-->26.3 and 39.2<!--> <!-->±<!--> <!-->7.9 µg/g wet weight of liver for ASG and AIG fractions in control rats and had no significant change in diabetes. In conclusion, diabetes is accompanied by the reduction in liver glycogen carbohydrate and protein of total and soluble fraction but the content of organic phosphate has not been affected.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"41 4","pages":"Pages 273-286"},"PeriodicalIF":1.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45303396","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}