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Journal of Carbohydrate Chemistry最新文献

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Chemoenzymatic synthesis of 6′-sialolactose-modified nanobody 6′-唾液乳糖修饰纳米体的化学酶合成
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2022-01-01 DOI: 10.1080/07328303.2022.2055048
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 ,&nbsp;Jie Zhao ,&nbsp;Guodong Mei ,&nbsp;Han Lin ,&nbsp;Haofei Hong ,&nbsp;Dan Li ,&nbsp;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}
引用次数: 1
Investigations to mechanism and applications of the glycosylation protocol employing 8-methyltosylaminoethynyl-1-naphthyl (MTEAN) glycoside donors 8-甲基甲酰基氨基乙基-1-萘基(MTEAN)糖苷供体糖基化机制及应用研究
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2022-01-01 DOI: 10.1080/07328303.2022.2045021
Si-Yu Zhou , Hui-Juan Liu , Qing-Ju Zhang , Jin-Xi Liao , De-Yong Liu , Ming-Dong Li , Jian-Song Sun
{"title":"Investigations to mechanism and applications of the glycosylation protocol employing 8-methyltosylaminoethynyl-1-naphthyl (MTEAN) glycoside donors","authors":"Si-Yu Zhou ,&nbsp;Hui-Juan Liu ,&nbsp;Qing-Ju Zhang ,&nbsp;Jin-Xi Liao ,&nbsp;De-Yong Liu ,&nbsp;Ming-Dong Li ,&nbsp;Jian-Song Sun","doi":"10.1080/07328303.2022.2045021","DOIUrl":"10.1080/07328303.2022.2045021","url":null,"abstract":"<div><p>Based on the capability of silyl ethers for efficient glycosylation, the new MTEAN glycosylation protocol utilizing 8-methyltosylaminoethynyl-1-naphthyl (MTEAN) glycosides as donors were extended to one-pot synthesis of nucleosides, late-stage modification of bioactive molecules, and stereoselective construction of 1,2-<em>cis</em>-glucosidic linkages using silyl ethers of the acceptors. Moreover, the reaction mechanism was systematically investigated by control reactions and side product characterizations, leading to the determination of a TfOH-catalyzed ynamide functionality-initiated process, which was further corroborated by identifications of the departure form of leaving group and the real catalyst.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"41 2","pages":"Pages 181-206"},"PeriodicalIF":1.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43129074","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}
引用次数: 1
A novel synthesis of tetrahydrocortisone 3-glucuronide 四氢化可的松3-葡萄糖醛酸盐的新合成方法
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2022-01-01 DOI: 10.1080/07328303.2021.2023559
Yan Zhang , Suqing Zhang , Rui Li , Jingshan Shen , Xiangrui Jiang , Haji A. Aisa
{"title":"A novel synthesis of tetrahydrocortisone 3-glucuronide","authors":"Yan Zhang ,&nbsp;Suqing Zhang ,&nbsp;Rui Li ,&nbsp;Jingshan Shen ,&nbsp;Xiangrui Jiang ,&nbsp;Haji A. Aisa","doi":"10.1080/07328303.2021.2023559","DOIUrl":"10.1080/07328303.2021.2023559","url":null,"abstract":"<div><p>A new route for the synthesis of tetrahydrocortisone 3-glucuronide has been developed with cortisone acetate as a starting material. The key step was using lithium tri-<em>tert</em>-butoxyaluminum hydride to reduce the C-3 carbonyl group of 5<em>β</em>-dihydrocortisone acetate (8) to provide 3<em>α</em>-5<em>β</em>-tetrahydrocortisone acetate (5). Then, Koenig–Knorr method was used for glycosylation with glycosyl bromide as the donor, cadmium carbonate as promoter and 4Å molecular sieves as dehydrating agent to give high yield of the desired product. The new route is shorter and gives higher yield than that reported in the literature.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"41 1","pages":"Pages 18-27"},"PeriodicalIF":1.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44680977","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}
引用次数: 0
Synthetic studies on naturally occurring sulfonium-type α-glucosidase inhibitors: progress and perspective 天然磺化型α-葡萄糖苷酶抑制剂的合成研究进展与展望
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2022-01-01 DOI: 10.1080/07328303.2022.2115508
Ying Ding , Jingyi Chen , Dan Liu , Jiahui Zhou , Wenxiang Tao , Zhizhong Yang , Genzoh Tanabe , Osamu Muraoka , Weijia Xie
{"title":"Synthetic studies on naturally occurring sulfonium-type α-glucosidase inhibitors: progress and perspective","authors":"Ying Ding ,&nbsp;Jingyi Chen ,&nbsp;Dan Liu ,&nbsp;Jiahui Zhou ,&nbsp;Wenxiang Tao ,&nbsp;Zhizhong Yang ,&nbsp;Genzoh Tanabe ,&nbsp;Osamu Muraoka ,&nbsp;Weijia Xie","doi":"10.1080/07328303.2022.2115508","DOIUrl":"10.1080/07328303.2022.2115508","url":null,"abstract":"<div><p>Extracts of <em>Salacia</em>, which are woody climbers mainly distributed in South Asian countries, have long been used to treat type-2 diabetes. Eight sulfonium-type α-glucosidase inhibitors salacinol, kotalanol, ponkoranol, salaprinol and their corresponding de-<em>O</em>-sulfonated analogues have been isolated so far. The unique structures, as well as distinguished biological activities, made them attractive targets in diverse research disciplines. The development of facile synthetic approaches is critical and fundamental for other extended investigations, including chemical biology and pharmaceutical development. This report provides an overview of the recent synthetic efforts directed toward the assembly of these sulfonium-containing polyhydroxylated natural products. This review will be helpful to gather insights into the development of a novel sulfonium type molecules with potential therapeutic applications.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"41 5","pages":"Pages 287-313"},"PeriodicalIF":1.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49250776","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}
引用次数: 0
A simpler and greener alternative route for anchoring carbohydrates with structural integrity on silica and glass supports 一个更简单和更环保的替代路线锚定碳水化合物与结构完整性的二氧化硅和玻璃支撑
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2022-01-01 DOI: 10.1080/07328303.2022.2121835
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 ,&nbsp;Manuel Azenha ,&nbsp;Galya Ivanova ,&nbsp;Carlos Pereira ,&nbsp;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}
引用次数: 0
Facile synthesis of novel 3H-1,5-benzodiazepine-derived aryl C-glycosides by coupling of sugar alkynes, acyl chlorides and 1, 2-phenylenediamine 糖炔、酰氯和1,2 -苯二胺偶联制备新型3h -1,5-苯二氮卓基芳基c -糖苷
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2022-01-01 DOI: 10.1080/07328303.2022.2045020
Qianxia Chen , Xiang Zhou , Fen Han , Fuyi Zhang , Yufen Zhao
{"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 ,&nbsp;Xiang Zhou ,&nbsp;Fen Han ,&nbsp;Fuyi Zhang ,&nbsp;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}
引用次数: 0
Synthesis of glucopyranoside benzimidazolium-based ionic liquids for Pd-catalyzed aqueous Suzuki reaction pd催化铃木反应中葡萄糖吡喃苷苯并咪唑基离子液体的合成
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2022-01-01 DOI: 10.1080/07328303.2022.2141770
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 ,&nbsp;Jian Wang ,&nbsp;Luan He ,&nbsp;Bisheng Wei ,&nbsp;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}
引用次数: 0
Structural characterization of water-soluble polysaccharides from Sophora flavescens Ait. and their anti-inflammatory activities based on NO release 苦参水溶性多糖的结构表征。以及基于NO释放的抗炎活性
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2022-01-01 DOI: 10.1080/07328303.2023.2174551
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 ,&nbsp;Bo-Wen Lu ,&nbsp;Si-Liang Jiang ,&nbsp;Cai-Xia Dong ,&nbsp;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}
引用次数: 0
Structural and conformational dynamics of human milk oligosaccharides, lacto-N-fucopentaose I and II, through molecular dynamics simulation 通过分子动力学模拟，研究人乳低聚糖，乳- n -fucopentaose I和II的结构和构象动力学
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2022-01-01 DOI: 10.1080/07328303.2022.2150203
B. Lalithamaheswari , C. Anu Radha
{"title":"Structural and conformational dynamics of human milk oligosaccharides, lacto-N-fucopentaose I and II, through molecular dynamics simulation","authors":"B. Lalithamaheswari ,&nbsp;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}
引用次数: 1
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 热水混合、共沉淀法和固态研磨法对β-环糊精(宿主)和芳香二胺(客体)包合物形成的比较研究
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2022-01-01 DOI: 10.1080/07328303.2022.2068026
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 ,&nbsp;Mitsuo Toda ,&nbsp;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}
引用次数: 0
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