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Journal of Carbohydrate Chemistry最新文献

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Synthesis of glycosylphosphatidylinositol analogues with an unnatural β-D-glucosamine-(1→6)-myo-inositol motif 具有非天然β-D-氨基葡萄糖-(1→6)-肌醇基团的糖基磷脂酰肌醇类似物的合成
IF 1.2 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2024-02-12 DOI: 10.1080/07328303.2024.2343004
{"title":"Synthesis of glycosylphosphatidylinositol analogues with an unnatural β-D-glucosamine-(1→6)-myo-inositol motif","authors":"","doi":"10.1080/07328303.2024.2343004","DOIUrl":"10.1080/07328303.2024.2343004","url":null,"abstract":"<div><p>Glycosylphosphatidylinositol (GPI) anchors contain a unique α-D-glucosamine-(1→6)-<em>myo</em>-inositol [αGlcN(1,6)Ins] motif in their conserved core structure. To facilitate investigations of the functional roles of this structural motif, two GPI analogues containing unnatural βGlcN(1,6)Ins, instead of αGlcN(1,6)Ins, and an alkyne group at different positions of the GPI core were designed and synthesized. To this end, an orthogonally protected pseudopentasaccharide derivative of GPIs with the βGlcN(1,6)Ins motif was convergently constructed via [3 + 2] glycosylation and used as the common intermediate to prepare both GPI analogues by streamlined synthetic protocols. The pseudopentasaccharide intermediate and developed protocols can be widely applicable to access various GPI analogues with the βGlcN(1,6)Ins motif. The target GPI analogues contain an alkyne, which allows their further modification to introduce various molecular labels via click chemistry, making them useful probes for the study of GPI anchorage. The differences in reactivity and NMR behavior of the two GPI analogues, as well as the differences of these analogues from previously reported GPI derivatives of similar structure containing an αGlcN(1,6)Ins motif, suggest that the 2-O-phosphoethanolamine moiety on mannose-I and the linkage form of GlcN in GPIs can have a decisive impact on the structure, which is likely relevant to biology.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"43 1","pages":"Pages 1-20"},"PeriodicalIF":1.2,"publicationDate":"2024-02-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140666500","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
Approaches related to the synthesis of Fmoc-Ser/Thr[GalNAc(Ac)3-α-D]-OH 与合成 Fmoc-Ser/Thr[GalNAc(Ac) 3 -α-D]-OH 有关的方法
IF 1.2 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2023-11-22 DOI: 10.1080/07328303.2024.2333417
Wenqiang Liu , Pan He , Shiying Shang , Zhongping Tan
{"title":"Approaches related to the synthesis of Fmoc-Ser/Thr[GalNAc(Ac)3-α-D]-OH","authors":"Wenqiang Liu ,&nbsp;Pan He ,&nbsp;Shiying Shang ,&nbsp;Zhongping Tan","doi":"10.1080/07328303.2024.2333417","DOIUrl":"10.1080/07328303.2024.2333417","url":null,"abstract":"<div><div>Protein <em>O</em>-glycosylation, particularly mucin-type glycosylation, plays important biological roles. However, the limited access to homogeneously glycosylated protein isoforms (glycoforms) has impeded the establishment of correlations between diverse glycan structures and protein properties, restricting therapeutic and diagnostic applications. Chemical synthesis of glycopeptides utilizing properly protected glycoamino acids as building blocks has emerged as a valuable approach to address the gap in glycoform acquisition. This review focuses on past efforts for the chemical synthesis of two fundamental glycoamino acid building blocks, Fmoc-Ser[GalNAc(Ac)<sub>3</sub>-α-D]-OH and Fmoc-Thr[GalNAc(Ac)<sub>3</sub>-α-D]-OH, by categorizing various methods based on glycosylation donors. The emphasis is on stereoselectivity, synthetic route length, and overall yield, with the goal of inspiring and guiding future research to further improve their synthetic efficiency and promote advancements in protein glycosylation studies and applications.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"42 7","pages":"Pages 223-251"},"PeriodicalIF":1.2,"publicationDate":"2023-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140753467","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
Syntheses of propargyl glycosides of disaccharides of the capsular polysaccharides from serotypes 4, 7F, and 9V Streptococcus pneumoniae for glycoconjugate vaccines 合成用于糖结合疫苗的 4、7F 和 9V 型肺炎链球菌荚膜多糖二糖的丙炔苷
IF 1.2 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2023-11-22 DOI: 10.1080/07328303.2024.2336004
Seth A. Taylor , Kendell White , Regan Patton , Anna Linder , Spencer Shin , Sophie Nelson , Jared Haymore , Joseph Zambrano , Marcus Hayden , Shawn Gubler , Tianyao Meng , M.G. Finn , Luc Teyton , Shenglou Deng , Paul B. Savage
{"title":"Syntheses of propargyl glycosides of disaccharides of the capsular polysaccharides from serotypes 4, 7F, and 9V Streptococcus pneumoniae for glycoconjugate vaccines","authors":"Seth A. Taylor ,&nbsp;Kendell White ,&nbsp;Regan Patton ,&nbsp;Anna Linder ,&nbsp;Spencer Shin ,&nbsp;Sophie Nelson ,&nbsp;Jared Haymore ,&nbsp;Joseph Zambrano ,&nbsp;Marcus Hayden ,&nbsp;Shawn Gubler ,&nbsp;Tianyao Meng ,&nbsp;M.G. Finn ,&nbsp;Luc Teyton ,&nbsp;Shenglou Deng ,&nbsp;Paul B. Savage","doi":"10.1080/07328303.2024.2336004","DOIUrl":"10.1080/07328303.2024.2336004","url":null,"abstract":"<div><div>We have developed a means of presenting relatively small glycans in a context to make them T cell-dependent antigens. This approach requires synthesis of glycans that remain close to carrier proteins upon conjugation, allowing T cell recognition and generation of B cells that produce high-affinity antibodies and memory toward target pathogens. In this work, we describe the syntheses of three disaccharides of the capsular polysaccharides from serotypes 4, 7F and 9V <em>Streptococcus pneumoniae</em> (<em>Sp</em>) as propargyl glycosides for use in this vaccine strategy. While variations of these disaccharides have previously been synthesized, none have been synthesized with an alkyne as the linker. Incorporation of the alkyne led to redesign of the synthesis of each disaccharide. All three disaccharides were synthesized without use of benzyl protective groups, one of the most used carbohydrate protective groups due to its stability and ease of removal via hydrogenation. We report challenges that arose while synthesizing the targets with less common protective groups, such as naphthyl ethers, and the methods used to successfully overcome these challenges.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"42 7","pages":"Pages 268-293"},"PeriodicalIF":1.2,"publicationDate":"2023-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140748003","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
Cyclopropylmethylidene as a versatile protecting group for carbohydrate synthesis 环丙基亚甲基作为碳水化合物合成的多功能保护基团
IF 1.2 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2023-11-22 DOI: 10.1080/07328303.2024.2332282
Xiaohua Li , Nasma Ibrahim , Zahraa Jaber , Sara Ali , Isha Masood
{"title":"Cyclopropylmethylidene as a versatile protecting group for carbohydrate synthesis","authors":"Xiaohua Li ,&nbsp;Nasma Ibrahim ,&nbsp;Zahraa Jaber ,&nbsp;Sara Ali ,&nbsp;Isha Masood","doi":"10.1080/07328303.2024.2332282","DOIUrl":"10.1080/07328303.2024.2332282","url":null,"abstract":"<div><div>Cyclopropylmethylidene has been developed as a versatile protecting group for carbohydrate synthesis. It can be formed by acid-catalyzed acetalization between cyclopropanecarboxaldehyde and 1,3-diols of sugar molecules. Selective reductive opening of the 4,6-O-cyclopropylmethylidene can be achieved to afford a C4 free hydroxyl group and a C6-cyclopropylmethyl (CPM) ether or vice versa. The cyclopropylmethylidene was found to be less stable than benzylidene under acidic conditions.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"42 7","pages":"Pages 294-308"},"PeriodicalIF":1.2,"publicationDate":"2023-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140210605","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
Poly(I:C)/c-GAMP/Alum ternary adjuvant system synergistically enhances the immunogenicity of glycopeptide antigen 聚(I:C)/c-GAMP/Alum三元佐剂系统可协同增强糖肽抗原的免疫原性
IF 1.2 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2023-11-22 DOI: 10.1080/07328303.2024.2332342
Shi-Hao Zhou , Yong-Ke Zou , Yan-Ling Liu , Ru-Yan Zhang , Yu Wen ,  Dong Ding , Jun Guo
{"title":"Poly(I:C)/c-GAMP/Alum ternary adjuvant system synergistically enhances the immunogenicity of glycopeptide antigen","authors":"Shi-Hao Zhou ,&nbsp;Yong-Ke Zou ,&nbsp;Yan-Ling Liu ,&nbsp;Ru-Yan Zhang ,&nbsp;Yu Wen ,&nbsp; Dong Ding ,&nbsp;Jun Guo","doi":"10.1080/07328303.2024.2332342","DOIUrl":"10.1080/07328303.2024.2332342","url":null,"abstract":"<div><div>The highly glycosylated mucin 1 (MUC1) serves as a promising target for cancer vaccines. However, the weak immunogenicity of MUC1 greatly impedes its application. Here, we covalently linked a MUC1 glycopeptide to carrier protein bovine serum albumin (BSA), and the resulting BSA-MUC1 conjugate was integrated with a ternary adjuvant system comprising TLR3 agonist poly(I:C), STING agonist c-GAMP, and Alum adjuvant. Compared to adjuvant-free and Alum-adjuvanted groups, the ternary adjuvant group induced 18.3- and 10.9-fold increases in MUC1-specific IgG titers, and effectively suppressed tumor growth. These findings may propose a straightforward yet highly effective strategy for designing vaccines, offering promising prospects in cancer treatment.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"42 7","pages":"Pages 252-267"},"PeriodicalIF":1.2,"publicationDate":"2023-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140370449","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
Respiratory Patterns in Neurological Injury, Pathophysiology, Ventilation Management, and Future Innovations: A Systematic Review. 神经损伤的呼吸模式、病理生理学、通气管理和未来创新：系统回顾。
4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2023-10-01 Epub Date: 2022-09-28 DOI: 10.14218/erhm.2022.00081
Matthew Goldman, Brandon Lucke-Wold, Jason Katz, Bavly Dawoud, Abeer Dagra
{"title":"Respiratory Patterns in Neurological Injury, Pathophysiology, Ventilation Management, and Future Innovations: A Systematic Review.","authors":"Matthew Goldman, Brandon Lucke-Wold, Jason Katz, Bavly Dawoud, Abeer Dagra","doi":"10.14218/erhm.2022.00081","DOIUrl":"10.14218/erhm.2022.00081","url":null,"abstract":"<p><p>Traumatic brain injuries (TBI), ischemic stroke, hemorrhagic stroke, brain tumors, and seizures have diverse and sometimes overlapping associated breathing patterns. Homeostatic mechanisms for respiratory control are intertwined with complex neurocircuitry, both centrally and peripherally. This paper summarizes the neurorespiratory control and pathophysiology of its disruption. It also reviews the clinical presentation, ventilatory management, and emerging therapeutics. This review additionally serves to update all recent preclinical and clinical research regarding the spectrum of respiratory dysfunction. Having a solid pathophysiological foundation of disruptive mechanisms would permit further therapeutic development. This novel review bridges experimental/physiological data with bedside management, thus allowing neurosurgeons and intensivists alike to rapidly diagnose and treat respiratory sequelae of acute brain injury.</p>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"20 1","pages":"338-349"},"PeriodicalIF":0.0,"publicationDate":"2023-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83026169","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
2021 JCC Best Paper Award 2021 年联合协调委员会最佳论文奖
IF 1.2 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2023-07-24 DOI: 10.1080/07328303.2024.2331282
Zhongwu Guo Ph.D.
{"title":"2021 JCC Best Paper Award","authors":"Zhongwu Guo Ph.D.","doi":"10.1080/07328303.2024.2331282","DOIUrl":"10.1080/07328303.2024.2331282","url":null,"abstract":"","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"42 4","pages":"Page 216"},"PeriodicalIF":1.2,"publicationDate":"2023-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140222305","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
Chemically modified starch with silicon quantum dots: Structures and properties 硅量子点化学修饰淀粉：结构与特性
IF 1.2 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2023-07-24 DOI: 10.1080/07328303.2024.2315529
Filiz Saman , Ebru Al , Bilge Boylu , Osman Arslan
{"title":"Chemically modified starch with silicon quantum dots: Structures and properties","authors":"Filiz Saman ,&nbsp;Ebru Al ,&nbsp;Bilge Boylu ,&nbsp;Osman Arslan","doi":"10.1080/07328303.2024.2315529","DOIUrl":"10.1080/07328303.2024.2315529","url":null,"abstract":"<div><div>Attachment of Silicon quantum dots (Si QDs) onto starch via sol-gel controlled covalent bonding to form hybrid starch particles was developed to modulate the optical, physical, and mechanical features of starch. Fabricated Si QDs chemically interacted with –OH side groups due to the sol-gel reactions on the starch molecules providing a detectable new molecular bonding to result in fluorescent emission. The produced structures formed nonlinear morphological orientations that provide a nanocomposite material platform for a facile molecular marking in daily applications.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"42 4","pages":"Pages 158-179"},"PeriodicalIF":1.2,"publicationDate":"2023-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139775828","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
2021 T. Ogawa Young Investigator Award
IF 1.2 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2023-07-24 DOI: 10.1080/07328303.2024.2331294
Zhongwu Guo Ph.D
{"title":"2021 T. Ogawa Young Investigator Award","authors":"Zhongwu Guo Ph.D","doi":"10.1080/07328303.2024.2331294","DOIUrl":"10.1080/07328303.2024.2331294","url":null,"abstract":"","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"42 4","pages":"Page 218"},"PeriodicalIF":1.2,"publicationDate":"2023-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143216743","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
2022 JCC Best Paper Award 2022 年联合协调委员会最佳论文奖
IF 1.2 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2023-07-24 DOI: 10.1080/07328303.2024.2331295
Zhongwu Guo Ph.D.
{"title":"2022 JCC Best Paper Award","authors":"Zhongwu Guo Ph.D.","doi":"10.1080/07328303.2024.2331295","DOIUrl":"10.1080/07328303.2024.2331295","url":null,"abstract":"","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"42 4","pages":"Page 219"},"PeriodicalIF":1.2,"publicationDate":"2023-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140223839","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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