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The structural diversity of natural glycosphingolipids (GSLs) 天然鞘糖脂的结构多样性
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2022-01-01 DOI: 10.1080/07328303.2022.2063308
Zhongwu Guo
{"title":"The structural diversity of natural glycosphingolipids (GSLs)","authors":"Zhongwu Guo","doi":"10.1080/07328303.2022.2063308","DOIUrl":"10.1080/07328303.2022.2063308","url":null,"abstract":"<div><p>Glycosphingolipids (GSLs) are a subclass of glycolipids made of a glycan and a ceramide that, in turn, is composed of a sphingoid base moiety and a fatty acyl group. GSLs represent the vast majority of glycolipids in eukaryotes, and as an essential component of the cell membrane, they play an important role in many biological and pathological processes. Therefore, they are useful targets for the development of novel diagnostic and therapeutic methods for human diseases. Since sphingosine was first described by J. L. Thudichum in 1884, several hundred GSL species, not including their diverse lipid forms that can further amplify the number of individual GSLs by many folds, have been isolated from natural sources and structurally characterized. This review tries to provide a comprehensive survey of the major GSL species, especially those with distinct glycan structures and modification patterns, and the ceramides with unique modifications of the lipid chains, that have been discovered to date. In particular, this review is focused on GSLs from eukaryotic species. This review has listed 251 GSL glycans with different linkages, 127 glycans with unique modifications, 46 sphingoids, and 43 fatty acyl groups. It should be helpful for scientists who are interested in GSLs, from isolation and structural analyses to chemical and enzymatic syntheses, as well as their biological studies and applications.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"41 2","pages":"Pages 63-154"},"PeriodicalIF":1.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"10427639","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
Design and synthesis of 4-azido-phosphatidylinositol as a potential probe for metabolic engineering of glycosylphosphatidylinositol on cells 设计与合成4-叠氮-磷脂酰肌醇作为糖基磷脂酰肌醇在细胞上代谢工程的潜在探针
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2022-01-01 DOI: 10.1080/07328303.2022.2077358
Kendall C. Craig , Zhongwu Guo
{"title":"Design and synthesis of 4-azido-phosphatidylinositol as a potential probe for metabolic engineering of glycosylphosphatidylinositol on cells","authors":"Kendall C. Craig ,&nbsp;Zhongwu Guo","doi":"10.1080/07328303.2022.2077358","DOIUrl":"10.1080/07328303.2022.2077358","url":null,"abstract":"<div><p>A diacyl phosphatidylinositol (PI) derivative with an azide linked to its inositol C4-position was effectively synthesized in 19 steps for the longest linear sequence and in a <em>ca</em>. 1% overall yield from 1,2-distearoyl-<em>sn</em>-glycerol and D-glucose. This compound was designed as a biosynthetic precursor of glycosylphosphatidylinositol (GPI) anchors. Its azide would enable further modification to introduce other molecular tags by a biocompatible click reaction. Therefore, it can be a useful probe for metabolic engineering of cell surface GPI anchors and GPI-anchored proteins.</p><p><span><figure><span><img><ol><li><span>Download : <span>Download high-res image (26KB)</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 4","pages":"Pages 238-248"},"PeriodicalIF":1.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"10474761","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: 2
Arabinogalactan from Ixeris chinensis (Thunb.) Nakai as a stabilizer to decorate SeNPs and enhance their anti-hepatocellular carcinoma activity via the mitochondrial pathway 阿拉伯半乳聚糖(阿拉伯语:Ixeris chinensis)Nakai作为一种稳定剂，通过线粒体途径修饰SeNPs并增强其抗肝癌活性
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2022-01-01 DOI: 10.1080/07328303.2022.2105860
Hongyan Li , Yifan Wang , Yan Chen , Shuxin Wang , Yifan Zhao , Jinyuan Sun
{"title":"Arabinogalactan from Ixeris chinensis (Thunb.) Nakai as a stabilizer to decorate SeNPs and enhance their anti-hepatocellular carcinoma activity via the mitochondrial pathway","authors":"Hongyan Li ,&nbsp;Yifan Wang ,&nbsp;Yan Chen ,&nbsp;Shuxin Wang ,&nbsp;Yifan Zhao ,&nbsp;Jinyuan Sun","doi":"10.1080/07328303.2022.2105860","DOIUrl":"10.1080/07328303.2022.2105860","url":null,"abstract":"<div><p>Arabinogalactan (ICPA) was isolated from the medicinal plant <em>Ixeris chinensis</em> (Thunb.) Nakai, and was used as the reducing agent to stabilize selenium nanoparticles (SeNPs). ICPA-decorated SeNPs (ICPA-SeNPs) were synthesized with Na<sub>2</sub>SeO<sub>3</sub> and ICPA, and their average diameter was 82.6<!--> <!-->±<!--> <!-->2.5 nm. ICPA-SeNPs had good dispersity in phosphate-buffered saline (PBS) with a hydrodynamic size of 156.2<!--> <!-->±<!--> <!-->2.8 nm. They were stable in PBS solution with a zeta potential of −24.8<!--> <!-->±<!--> <!-->0.6 mV. The anti-hepatoma activity of ICPA-SeNPs was investigated <em>in vitro</em>. ICPA-SeNPs significantly suppressed the growth of SMMC-7721 and HepG2 hepatoma cells. They entered SMMC-7721 cells via energy- and caveolae-dependent endocytosis. ICPA-SeNPs were able to increase reactive oxygen species levels, reduce mitochondrial membrane potential, and increase caspase-3 expression in SMMC-7721 cells, which led to the apoptosis of SMMC-7721 cells. They also arrested the cell cycle of SMMC-7721 cells in the S phase. These findings indicate that ICPA could enhance the stability of SeNPs and inhibit SMMC-7721 cell proliferation via the mitochondrial pathway. ICPA-SeNPs could be developed as an antitumor agent for hepatocellular carcinoma treatment.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"41 5","pages":"Pages 329-345"},"PeriodicalIF":1.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49111345","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
An efficient method for the cleavage of tert-butyldiphenylsilyl ethers catalyzed by 1,3-dibromo-5,5-dimethylhydantoin 1,3-二溴-5,5-二甲基乙内酰脲催化叔丁基二苯基甲硅烷基醚裂解的有效方法
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2022-01-01 DOI: 10.1080/07328303.2022.2031206
Zong Han
{"title":"An efficient method for the cleavage of tert-butyldiphenylsilyl ethers catalyzed by 1,3-dibromo-5,5-dimethylhydantoin","authors":"Zong Han","doi":"10.1080/07328303.2022.2031206","DOIUrl":"10.1080/07328303.2022.2031206","url":null,"abstract":"Abstract An efficient method for the deprotection of tert-butyldiphenylsilyl (TBDPS) ethers using 1,3-dibromo-5,5-dimethylhydantoin (DBH) as catalyst and dimethyl sulfoxide (DMSO) as solvent has been established. This method is useful for many kinds of compounds, such as carbohydrates, steroids, benzyl alcohols and primary fatty alcohols. Substrates bearing acetates, benzoates, pivaloates, mesylates, and benzyl and p-methoxybenzyl ethers are compatible. Graphical abstract","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"41 1","pages":"Pages 51-62"},"PeriodicalIF":1.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41626808","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
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
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