Marijana Petković , Jenny Leopold , Iva Popović , Dušan Dimić , Jelica Ilić , Miloš Nenadović , Zlatko Rakočević , Jürgen Schiller
{"title":"Performances of ionic liquid matrices with butyl ammonium counterion for matrix-assisted laser desorption/ionization mass spectrometric detection and analysis of sucralfate","authors":"Marijana Petković , Jenny Leopold , Iva Popović , Dušan Dimić , Jelica Ilić , Miloš Nenadović , Zlatko Rakočević , Jürgen Schiller","doi":"10.1080/07328303.2019.1669633","DOIUrl":"10.1080/07328303.2019.1669633","url":null,"abstract":"<div><p>In this work, the performances of two ionic liquid matrices (ILMs) with the same ammonium counterpart for mass spectrometric analysis of the insoluble and soluble sucralfate were compared. Matrix-assisted laser desorption/ionization mass spectrometry (MALDI MS) was performed assisted by the butylammonium salts of α-cyano-hydroxycinnamic acid (CHCAB) and 2,5-dihydroxybenzoic acid (DHBB). CHCAB has a higher IE than DHBB, but better optical properties. CHCAB is more suitable for the analysis of sucralfate, although molecular ions of both compounds were detectable only with low intensities. Thus, optical properties of ILMs are crucial to enhance the sensitivity of MALDI MS detection of polysulfated oligosaccharides.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"39 1","pages":"Pages 1-23"},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2019.1669633","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44092757","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}
Chunjun Qin , Zhonghua Liu , Meiru Ding , Juntao Cai , Junjie Fu , Jing Hu , Peter H. Seeberger , Jian Yin
{"title":"Chemical synthesis of the Pseudomonas aeruginosa O11 O-antigen trisaccharide based on neighboring electron-donating effect","authors":"Chunjun Qin , Zhonghua Liu , Meiru Ding , Juntao Cai , Junjie Fu , Jing Hu , Peter H. Seeberger , Jian Yin","doi":"10.1080/07328303.2020.1839479","DOIUrl":"10.1080/07328303.2020.1839479","url":null,"abstract":"<div><p><em>Pseudomonas aeruginosa</em> O11 O-antigen is immunologically active but an exact protective epitope has not yet been identified. Synthesis of O11 O-antigen trisaccharide is of importance for identifying the epitopes. Here, neighboring electron-donating effects are keys to enhance the nucleophilicity of the C3 hydroxyl groups of D- and L-fucosamines, to facilitate the efficient synthesis of the trisaccharide. The disarmed peracetylated glycosyl donor with low glycosylation reactivity and glycosyl trifluoroacetimidate with good stability allowed for the glycosylation under mild conditions. The C6 nucleophilic tosylate substitution of D-galactose with iodine was found to be dependent on the steric effect of the axial C4.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"39 8","pages":"Pages 374-397"},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2020.1839479","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47356855","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}
Jassem G. Mahdi , Hanaa M. Dawoud , Abigail J. Manning , Harvey F. Lieberman , David R. Kelly
{"title":"Synthesis of unstable 4-benzoyl-1,6-anhydro-3-keto-β-D-mannopyranose via stereoselective photobromination of 2,3-isopropylidene-4-benzoyl-1,6-anhydro-β-D-mannopyranose","authors":"Jassem G. Mahdi , Hanaa M. Dawoud , Abigail J. Manning , Harvey F. Lieberman , David R. Kelly","doi":"10.1080/07328303.2019.1663204","DOIUrl":"10.1080/07328303.2019.1663204","url":null,"abstract":"<div><p>Stereoselective photobromination of 1,6-anhydro-β-D-glucopyranose derivatives occurs at <em>exo</em>-H6. However, photobromination of 4-benzoyl-2,3-isopropylidene-1,6-anhydro-β-D-mannopyranose <strong>6</strong> produced unstable 4-benzoyl-1,6-anhydro-3-keto-β-D-mannopyranose <strong>7</strong>. The mechanism of stereoselective oxidation at C-3 could be attributed to the facile radical proton abstraction at C-3, followed by the subsequent bromination of the isopropylidene group, which was subsequently eliminated during the aqueous workup. Thus, the aim of this article is to identify the molecular structure of the unstable compound <strong>7</strong>.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"39 1","pages":"Pages 24-35"},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2019.1663204","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41768010","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}
Lang Lin , Jie Yang , Yan Yang , Hui Zhi , Xin Hu , Dongkun Chai , Yunjie Liu , Xiaojun Shen , Jie Wang , Yunqi Song , Aimei Zeng , Xinyu Li , Haibo Feng
{"title":"Phosphorylation of Radix Cyathula officinalis polysaccharide improves its immune-enhancing activity","authors":"Lang Lin , Jie Yang , Yan Yang , Hui Zhi , Xin Hu , Dongkun Chai , Yunjie Liu , Xiaojun Shen , Jie Wang , Yunqi Song , Aimei Zeng , Xinyu Li , Haibo Feng","doi":"10.1080/07328303.2019.1700996","DOIUrl":"10.1080/07328303.2019.1700996","url":null,"abstract":"<div><p>In this study, the effects of phosphorylation of <em>Radix Cyathula officinalis</em> polysaccharide (RCPS) on its immunological properties were evaluated using broiler chickens immunized with Newcastle disease vaccine (NDV). The results suggested that phosphorylated RCPS (pRCPS) could enhance antibody titers against NDV vaccination, improve the indexes of thymus, the bursa of fabricius and spleen, and up-regulate IL-2, IL-4, IL-5, IL-6, IL-10, and IFN-γ. Overall, pRCPS could significantly improve cellular and humoral immune responses in broiler chickens immunized with NDV and thus represents a useful immunotherapeutic agent.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"39 1","pages":"Pages 50-62"},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2019.1700996","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42728827","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}
Zhi-ling Cao , Cong Zhu , Wen-ying Wu , Dan-dan Zhu , Dong Qian , Jian Zhu , Tian-ge Chang , Mei Sheng , Xiu-li Yang , Wei-wei Liu
{"title":"Synthesis of β-acylamino furans from glucosamine","authors":"Zhi-ling Cao , Cong Zhu , Wen-ying Wu , Dan-dan Zhu , Dong Qian , Jian Zhu , Tian-ge Chang , Mei Sheng , Xiu-li Yang , Wei-wei Liu","doi":"10.1080/07328303.2021.1895195","DOIUrl":"10.1080/07328303.2021.1895195","url":null,"abstract":"<div><p>A facile method for the synthesis of a series of novel <em>β</em>-acylamino furans stating from renewable monosaccharide was achieved. Glucosamine hydrochloride was selectively <em>N</em>-acylated with acyl chlorides in methanol/triethylamine to yield <em>N</em>-acyl-<span>d</span><strong>-</strong>glucosamines, which were subsequently converted into <em>β</em>-acylamino furans through dehydration and cyclization under microwave irradiation.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"39 9","pages":"Pages 472-484"},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2021.1895195","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45135356","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}
Han Ding , Xin Zhou , Qian Yao , Peng Wang , Ming Li
{"title":"Oxidative radical decarboxylation of uronic acids: Convenient synthesis of C-Glycosylated isoquinolines","authors":"Han Ding , Xin Zhou , Qian Yao , Peng Wang , Ming Li","doi":"10.1080/07328303.2019.1709974","DOIUrl":"10.1080/07328303.2019.1709974","url":null,"abstract":"<div><p>An expedient approach to <em>C</em>-glycosylated isoquinolines was established based on the coupling of vinyl isonitriles with tetrafuranos-4-yl and pentapyranos-5-yl radicals generated from oxidative decarboxylation of uronic acids derived from monosaccharides and complex oligosaccharides. This approach enjoyed a broad substrate scope and good functional group tolerance, and afforded structurally diverse <em>C</em>-glycosylated isoquinolines in the presence or absence of silver salts. Deprotection of the coupling products was conducted to yield <em>C</em>-glycosylated isoquinolines with multiple hydroxyl groups. These novel architectures would offer opportunities for investigation of their bioactivities.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"39 2","pages":"Pages 75-106"},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2019.1709974","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43678792","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}
Kunj B. Mishra , Sanchayita Rajkhowa , Vinod K. Tiwari
{"title":"An expeditious one-pot synthesis of thiourea derivatives of carbohydrates from sugar azides","authors":"Kunj B. Mishra , Sanchayita Rajkhowa , Vinod K. Tiwari","doi":"10.1080/07328303.2020.1822997","DOIUrl":"10.1080/07328303.2020.1822997","url":null,"abstract":"<div><p>A facile and practical route for the high-yielding synthesis of various thiourea derivatives of carbohydrates has been accomplished through the coupling of carbohydrate-based azides and amines under Staudinger condition (PPh<sub>3</sub>/CS<sub>2</sub>). Structures of all the developed compounds have been elucidated using various spectroscopic techniques, including NMR, IR, and MS. Weak interactions within compound <strong>3a</strong> have also been discussed through the analysis of its single crystal X-ray data.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"39 7","pages":"Pages 334-353"},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2020.1822997","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49101473","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}
Hye Rin Park , Jihyun Kang , Shin-Joung Rho , Yong-Ro Kim
{"title":"Structural and physicochemical properties of enzymatically modified rice starch as influenced by the degree of enzyme treatment","authors":"Hye Rin Park , Jihyun Kang , Shin-Joung Rho , Yong-Ro Kim","doi":"10.1080/07328303.2020.1788574","DOIUrl":"10.1080/07328303.2020.1788574","url":null,"abstract":"<div><p>The structure and physicochemical properties of rice starch modified with 4-α-glucanotransferase (4αGTase) were compared for different enzyme treatment times (1, 24, and 96 h). Specifically, the gelation properties of native rice starch and 4αGTase-treated rice starch (GS) were analyzed regarding their structural characteristics. The average molecular weight of GS decreased with increasing treatment time, and was 4.73 × 10<sup>4</sup> g/mol after 96 h of treatment. The chain length distribution was also broadened with the enzyme treatment, as 4αGTase transferred α-glucan from one chain to another. The enzyme treatment also altered the gelation properties and decreased the viscosity of the starch depending on the treatment time, perhaps due to the changes in molecular weight distribution and branched chain length distribution. Moreover, the overall characteristics of GS differed significantly from those of maltodextrin. The physicochemical characteristics of GS with different degrees of 4αGTase treatment suggest that it can be used in the food and pharmaceutical industries.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"39 5","pages":"Pages 250-266"},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2020.1788574","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46272475","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":"Mimicking the transition state of reactions of glycoside hydrolases: Updating the conformational space of the oxocarbenium cation","authors":"Santiago Alonso-Gil","doi":"10.1080/07328303.2020.1766481","DOIUrl":"10.1080/07328303.2020.1766481","url":null,"abstract":"<div><p>One strategy for developing glycoside hydrolase (GH) inhibitors is to mimic the conformation of the transition state (TS) along the hydrolysis reaction coordinate. We present a DFT-based model to understand the conformational space of the oxocarbenium cation as a TS in carbohydrate chemistry. Using Bolzano’s theorem, we have demonstrated the existence of a function that divides the puckering coordinate space. These results are compared with the available experimental crystal structures of GH-inhibitor complexes, and a contradictory case (GH92) was computationally studied. Our mathematical model opens a door to design more specific inhibitors and to decipher the catalytic pathways of controversial cases.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"39 4","pages":"Pages 175-188"},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2020.1766481","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46432279","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}
Zhonggao Zhou , Jing Li , Yue Wu , Yangyang Yuan , Lingfang Kong , Jun Xue , Zhiqiang Huang
{"title":"Glucopyranoside-substituted imidazolium-based chiral ionic liquids for Pd-catalyzed homo-coupling of arylboronic acids in water","authors":"Zhonggao Zhou , Jing Li , Yue Wu , Yangyang Yuan , Lingfang Kong , Jun Xue , Zhiqiang Huang","doi":"10.1080/07328303.2020.1788573","DOIUrl":"10.1080/07328303.2020.1788573","url":null,"abstract":"<div><p>Chiral ionic liquids (CILs) are widely used solvents and materials with prominent properties. Carbohydrate-derived imidazolium-based CILs represent a distinctive type of CILs possessing multiple chiral centers from natural chiral pool. Herein, a series of glucopyranoside-substituted imidazolium-based CILs (Glu-imi-CILs) were synthesized and evaluated as ligands for Pd-catalyzed homo-coupling reactions of arylboronic acids in water. The glucopyranoside substituent was instrumental for improving the catalytic activity of the resulting catalysts. Moreover, a Glu-imi-CIL with a free hydroxyl group for additional coordination was found to be the most efficient ligand. A series of symmetric biaryl compounds (13 examples) were synthesized from arylboronic acids by this method in high isolated yields (85−99%).</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"39 5","pages":"Pages 288-299"},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2020.1788573","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42047714","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}