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Journal of Carbohydrate Chemistry最新文献

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Mimicking the transition state of reactions of glycoside hydrolases: Updating the conformational space of the oxocarbenium cation 模拟糖苷水解酶反应的过渡态:更新氧羰基阳离子的构象空间
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2020-01-01 DOI: 10.1080/07328303.2020.1766481
Santiago Alonso-Gil
{"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":null,"pages":null},"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}
引用次数: 1
Structural and physicochemical properties of enzymatically modified rice starch as influenced by the degree of enzyme treatment 酶处理程度对酶改大米淀粉结构和理化性质的影响
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2020-01-01 DOI: 10.1080/07328303.2020.1788574
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 ,&nbsp;Jihyun Kang ,&nbsp;Shin-Joung Rho ,&nbsp;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":null,"pages":null},"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}
引用次数: 7
Glucopyranoside-substituted imidazolium-based chiral ionic liquids for Pd-catalyzed homo-coupling of arylboronic acids in water 葡萄糖吡喃苷取代咪唑基手性离子液体用于pd催化芳基硼酸在水中的均偶联
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2020-01-01 DOI: 10.1080/07328303.2020.1788573
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 ,&nbsp;Jing Li ,&nbsp;Yue Wu ,&nbsp;Yangyang Yuan ,&nbsp;Lingfang Kong ,&nbsp;Jun Xue ,&nbsp;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":null,"pages":null},"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}
引用次数: 6
Isolation and structural identification of a novel fructan from Radix Codonopsis 党参中一种新果聚糖的分离与结构鉴定
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2020-01-01 DOI: 10.1080/07328303.2020.1772278
Jiankuan Li , Yan Wang , Xia Zhang , Lingya Cao , Jiaojiao Ji , Qinghong Zheng , Jianping Gao
{"title":"Isolation and structural identification of a novel fructan from Radix Codonopsis","authors":"Jiankuan Li ,&nbsp;Yan Wang ,&nbsp;Xia Zhang ,&nbsp;Lingya Cao ,&nbsp;Jiaojiao Ji ,&nbsp;Qinghong Zheng ,&nbsp;Jianping Gao","doi":"10.1080/07328303.2020.1772278","DOIUrl":"10.1080/07328303.2020.1772278","url":null,"abstract":"<div><p>Fructans are generally divided into two different types: <em>β</em>-D-fructofuranosyl-(2→1)-linked inulin and <em>β</em>-D-fructofuranosyl-(2→6)-linked levan. Previously, Radix Codonopsis was found to be rich in inulin type of fructans with low molecular weight (&lt;5000 Da). In this study, a novel macromolecular fructan with a molecular weight of 1.70 × 10<sup>3</sup> KD was isolated from Radix Codonopsis, and its homogeneity was shown to be a single peak by high performance gel permeation chromatography (HPGPC), and its structure was confirmed to contain a new type of linkage, <em>α</em>-D-fructofuranosyl-(2→3)-<em>β</em>-D-fructofuranosyl linkage, by 1D- and 2D-nuclear magnetic resonance (NMR).</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2020.1772278","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42363531","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: 8
Synthesis of oligosaccharide fragments of capsular polysaccharide Staphylococcus aureus type 8 8型金黄色葡萄球菌荚膜多糖低聚糖片段的合成
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2020-01-01 DOI: 10.1080/07328303.2020.1821042
Satsawat Visansirikul , Stephen A. Kolodziej , Alexei V. Demchenko
{"title":"Synthesis of oligosaccharide fragments of capsular polysaccharide Staphylococcus aureus type 8","authors":"Satsawat Visansirikul ,&nbsp;Stephen A. Kolodziej ,&nbsp;Alexei V. Demchenko","doi":"10.1080/07328303.2020.1821042","DOIUrl":"10.1080/07328303.2020.1821042","url":null,"abstract":"<div><p>To enhance our understanding of the activation and conjugation processes, reported herein is the synthesis of oligosaccharides comprising two sequential repeating units of capsular polysaccharide <em>S. aureus</em> serotype 8 (CP8). As in our previous syntheses of staphylococcal oligosaccharides, the potential propagation positions are blocked with methyl groups. While protein conjugates of carbohydrate antigens based on the structure of the <em>S. aureus</em> capsular serotypes have the potential to contribute to a <em>S. aureus</em> vaccine, despite promising preclinical data, efficacy has not been detected in human populations thus far.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2020.1821042","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45495848","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: 4
Sequential one-pot synthesis of (1→6) amide-linked oligosaccharide mimetics under mild conditions （1）的顺序一锅合成→6） 温和条件下的酰胺连接寡糖模拟物
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2020-01-01 DOI: 10.1080/07328303.2020.1798456
Shuang Hao , Shuai Lin , Xin Wang , Ran An , Mengbi Guo , Yuanxin Wang , Xue Cheng , Hang Xu , Xiaoguang Yang , Zhuang Hou , Chun Guo
{"title":"Sequential one-pot synthesis of (1→6) amide-linked oligosaccharide mimetics under mild conditions","authors":"Shuang Hao ,&nbsp;Shuai Lin ,&nbsp;Xin Wang ,&nbsp;Ran An ,&nbsp;Mengbi Guo ,&nbsp;Yuanxin Wang ,&nbsp;Xue Cheng ,&nbsp;Hang Xu ,&nbsp;Xiaoguang Yang ,&nbsp;Zhuang Hou ,&nbsp;Chun Guo","doi":"10.1080/07328303.2020.1798456","DOIUrl":"10.1080/07328303.2020.1798456","url":null,"abstract":"<div><p>An efficient and practical synthetic strategy, suitable for one-pot synthesis, for novel amide-linked oligosaccharide mimetics from sugar amino acid precursors is described. Twenty substrates, including twelve amide-linked disaccharide mimetics, four amide-linked trisaccharide mimetics and four amide-linked tetrasaccharide mimetics, were synthesized based on this strategy and its optimal conditions. This potentially general method is featured by high yields, gram-scale synthesis, wide substrate scope, and mild reaction conditions.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2020.1798456","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45359471","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
1H NMR analysis of perdeutero N-sulfoheparosan C5-epimerization: a direct way to measure the activity of immobilized C5-epimerase perdeutero - N-sulfoheparosan C5-epimerization的1H NMR分析:一种直接测量固定化C5-epimerase活性的方法
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2020-01-01 DOI: 10.1080/07328303.2021.1903026
Meng Qiao , Ruoyu Jiao , Xing Zhang , Zhengzhang Wu , Baoxing Shen , Bingzhi Li
{"title":"1H NMR analysis of perdeutero N-sulfoheparosan C5-epimerization: a direct way to measure the activity of immobilized C5-epimerase","authors":"Meng Qiao ,&nbsp;Ruoyu Jiao ,&nbsp;Xing Zhang ,&nbsp;Zhengzhang Wu ,&nbsp;Baoxing Shen ,&nbsp;Bingzhi Li","doi":"10.1080/07328303.2021.1903026","DOIUrl":"10.1080/07328303.2021.1903026","url":null,"abstract":"<div><p>D-Glucuronyl C5-epimerase (C5-epi), which converts D-glucuronic acid to L-iduronic acid, is a crucial enzyme in the preparation of bioengineered heparin, which provides an alternative way to produce safer heparins. Herein, we provided an efficient way to measure the activity of cyanogen bromide-immobilized C5-epi based on proton nuclear magnetic resonance (NMR) analysis of perdeutero <em>N</em>-sulfoheparosan C5-epimerization. In this method, reactions catalyzed by C5-epi could be monitored by real-time 1 D NMR according to the peak intensity change of H-5 from IdoA and GlcA residues in the <sup>1</sup>H NMR spectrum, which is nondestructive of sample and also serves the kinetic property evaluation of immobilized C5-epi.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2021.1903026","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46740501","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
FeCl3/C as an efficient catalyst for Ferrier rearrangement of 3,4,6-tri-O-Benzyl-D-glucal FeCl3/C作为3,4,6-三- o -苄基- d -葡聚糖铁离子重排的高效催化剂
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2020-01-01 DOI: 10.1080/07328303.2020.1788575
Yuling Mei , Youxian Dong , Juan Li , Bo Zhang , Guosheng Sun , Jiafen Zhou , Wenshuai Si , Yiwen Han , Zhenliang Wu , Jianbo Zhang
{"title":"FeCl3/C as an efficient catalyst for Ferrier rearrangement of 3,4,6-tri-O-Benzyl-D-glucal","authors":"Yuling Mei ,&nbsp;Youxian Dong ,&nbsp;Juan Li ,&nbsp;Bo Zhang ,&nbsp;Guosheng Sun ,&nbsp;Jiafen Zhou ,&nbsp;Wenshuai Si ,&nbsp;Yiwen Han ,&nbsp;Zhenliang Wu ,&nbsp;Jianbo Zhang","doi":"10.1080/07328303.2020.1788575","DOIUrl":"10.1080/07328303.2020.1788575","url":null,"abstract":"<div><p>FeCl<sub>3</sub>/C was used as an efficient and convenient promoter for glycosylation through Ferrier-type rearrangement of 3,4,6-tri-<em>O</em>-benzyl-D-glucal, which is a relatively unreactive substrate for this type of reaction. The method was applicable to a wide range of alcohols, especially phenols. A series of 2,3-unsaturated-<em>O</em>-glucosides were prepared efficiently (47–92%) by this method under mild conditions.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2020.1788575","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48353696","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
Synthesis and nondestructive detailed structure characterization of carboxymethyl xylan from bagasse 甘蔗渣羧甲基木聚糖的合成及无损精细结构表征
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2020-01-01 DOI: 10.1080/07328303.2020.1748643
Lei Wang , Xiangxiang Qin , Xueyan Miao , Haishan Chen , Yuheng Zhou , Aihua Cai
{"title":"Synthesis and nondestructive detailed structure characterization of carboxymethyl xylan from bagasse","authors":"Lei Wang ,&nbsp;Xiangxiang Qin ,&nbsp;Xueyan Miao ,&nbsp;Haishan Chen ,&nbsp;Yuheng Zhou ,&nbsp;Aihua Cai","doi":"10.1080/07328303.2020.1748643","DOIUrl":"10.1080/07328303.2020.1748643","url":null,"abstract":"<div><p>Carboxymethyl xylan (CMX) was synthesized and characterized. A method based on quantitative <sup>13</sup>C NMR was developed to obtain detailed structural information. The total degree of substitution (DS), partial DS at 2- and 3-<em>O</em>-positions, and the quantitation of each unit in CMX could be acquired simultaneously by this method without decomposing the polymer backbone, thus avoiding errors caused by polymer hydrolysis with traditional methods using HPLC and <sup>1</sup>H NMR spectrometry. Moreover, different from methods of direct detection of carboxyl groups, such as acidometric and potentiometric titrations, this method was not affected by probable impurity introduced during carboxymethylation.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2020.1748643","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48465782","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: 4
GM3 trisaccharide biosynthesis and process optimization using engineered E. coli lysate and whole-cell catalysis 利用工程大肠杆菌裂解物和全细胞催化合成GM3三糖及其工艺优化
IF 1 4区 化学
Journal of Carbohydrate Chemistry Pub Date : 2020-01-01 DOI: 10.1080/07328303.2020.1788576
Lipeng Feng , Jie Shi , Haofei Hong , Zhifang Zhou , Zhimeng Wu
{"title":"GM3 trisaccharide biosynthesis and process optimization using engineered E. coli lysate and whole-cell catalysis","authors":"Lipeng Feng ,&nbsp;Jie Shi ,&nbsp;Haofei Hong ,&nbsp;Zhifang Zhou ,&nbsp;Zhimeng Wu","doi":"10.1080/07328303.2020.1788576","DOIUrl":"10.1080/07328303.2020.1788576","url":null,"abstract":"<div><p>An engineered <em>E. coli</em> strain BL21 (DE3, SiaB, PmST3, △<em>lacZ</em>, △<em>nanZ</em>) that simultaneously encoded CMP-Neu5Ac synthase (SiaB) and α-2-3-sialyltransferase (PmST3) was constructed to synthesize GM3 trisaccharide. The crude <em>E. coli</em> lysate could be readily used for biosynthesis of GM3 trisaccharide with a nearly quantitative yield under optimal conditions. In addition, this engineered <em>E. coli</em> strain as whole-cell catalyst could generate approximately 1 g of GM3 trisaccharide in 40 mL of medium under optimal conditions. The whole-cell catalyst could be recycled and reused for at least 3 rounds without obvious loss of enzymatic activity.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":null,"pages":null},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2020.1788576","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42110190","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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