Carbohydrate Research最新文献

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Identification of N-linked glycans recognized by WGA in saliva from patients with non-small cell lung cancer 鉴定非小细胞肺癌患者唾液中 WGA 识别的 N-连接聚糖。
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2024-09-03 DOI: 10.1016/j.carres.2024.109256
Fan Zhang , Zhen Tang , Haoqi Du , Yuzi Wang , Jiabao Du , Zeyu Zhao , Zheng Li
{"title":"Identification of N-linked glycans recognized by WGA in saliva from patients with non-small cell lung cancer","authors":"Fan Zhang ,&nbsp;Zhen Tang ,&nbsp;Haoqi Du ,&nbsp;Yuzi Wang ,&nbsp;Jiabao Du ,&nbsp;Zeyu Zhao ,&nbsp;Zheng Li","doi":"10.1016/j.carres.2024.109256","DOIUrl":"10.1016/j.carres.2024.109256","url":null,"abstract":"<div><p>Non-small cell lung cancer (NSCLC) is one of the leading causes of cancer-related deaths. Saliva diagnosis is an essential approach for clinical applications owing to its noninvasive and material-rich features. The purpose of this study was to investigate differences in <em>wheat germ agglutinin</em> (WGA)-based recognition of salivary protein N-linked glycan profiles to distinguish non-small cell lung cancer (NSCLC) patients from controls. We used WGA-magnetic particle conjugates to isolate glycoproteins in the pooled saliva of healthy volunteers (HV, n = 35), patients with benign pulmonary disease (BPD, n = 35), lung adenocarcinoma (ADC, n = 35), and squamous cell carcinoma (SCC, n = 35), following to release the N-linked glycans from the isolated proteins with PNGase F, and further identified and annotated the released glycans by MALDI-TOF/TOF-MS, respectively. The results showed that 34, 35, 39, and 44 N-glycans recognized by WGA were identified and annotated from pooled saliva samples of HV, BPD, ADC, and SCC, respectively. Furthermore, the proportion of N-glycans recognized by WGA in BPD (81.2 %), ADC (90.1 %), and SCC (88.7 %), increased compared to HV (71.9 %). Two N-glycan peaks (<em>m</em>/<em>z</em> 2286.799, and 3399.211) specifically recognized by WGA were present only in NSCLC. These findings suggest that altered salivary glycopatterns such as sialic acids and GlcNAc containing N-glycans recognized by WGA might serve as potential personalized biomarkers for the diagnosis of NSCLC patients.</p></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109256"},"PeriodicalIF":2.4,"publicationDate":"2024-09-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142145257","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
5-Fluorouracil-loaded green chitosan nanoparticles/ guar gum nanocomposite hydrogel in controlled drug delivery 5-氟尿嘧啶负载的绿色壳聚糖纳米颗粒/瓜尔胶纳米复合水凝胶在控制给药中的应用
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2024-09-03 DOI: 10.1016/j.carres.2024.109257
Ganeswar Dalei , Debasis Jena , Subhraseema Das
{"title":"5-Fluorouracil-loaded green chitosan nanoparticles/ guar gum nanocomposite hydrogel in controlled drug delivery","authors":"Ganeswar Dalei ,&nbsp;Debasis Jena ,&nbsp;Subhraseema Das","doi":"10.1016/j.carres.2024.109257","DOIUrl":"10.1016/j.carres.2024.109257","url":null,"abstract":"<div><p>In recent years nanotechnologies have been applied to human health with promising results, especially in the field of drug delivery. Polymeric nanoparticles (NPs) have garnered much importance in controlled drug delivery owing to their size. Chitosan (Cs) is a well-recognized biopolymer and Cs NPs have been widely explored in drug delivery. Nonetheless, reports pertaining to green synthesis of Cs NPs are scarce. Thus, in this study, green synthesis of Cs NPs was accomplished from raw mango peel extract. Spherical Cs NPs with positively charged surface of 33.4 mV was accomplished by this process. Cs NPs, in varied content, were integrated in a guar gum network matrix resulting in a nanocomposite hydrogel. The mechanical and thermal stability of the hydrogel improved upon addition of Cs NPs. The hydrogel exhibited smart swelling, good antioxidant and anti-inflammatory propensities. Cs NPs encapsulating 5-Fluorouracil demonstrated a controlled release drug profile in the colorectum and the kinetics implied the anomalous nature of drug release mechanism. The exposure of the drug-loaded nanocomposite hydrogel displayed improved anticancer effects in HT-29 colon cancer cells. Taken altogether, this study puts forth the greater efficacy of Cs NPs in controlled drug delivery for anticancer therapy.</p></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109257"},"PeriodicalIF":2.4,"publicationDate":"2024-09-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142139381","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 and characterization of modified chitosan as a promising material for enterosorption of heavy metal ions 改性壳聚糖的合成与表征--一种有前途的重金属离子肠道吸附材料
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2024-08-31 DOI: 10.1016/j.carres.2024.109255
S.S. Fatullayeva , D.B. Tagiyev , N.A. Zeynalov , M.G. Raucci , E. Amendola , G. Gomez d’Ayala , A.D. Guliyev , ShD. Tagiyev , M.R. Marcedula , C. Demitri , A.R. Guliyeva , R.H. Suleymanova
{"title":"Synthesis and characterization of modified chitosan as a promising material for enterosorption of heavy metal ions","authors":"S.S. Fatullayeva ,&nbsp;D.B. Tagiyev ,&nbsp;N.A. Zeynalov ,&nbsp;M.G. Raucci ,&nbsp;E. Amendola ,&nbsp;G. Gomez d’Ayala ,&nbsp;A.D. Guliyev ,&nbsp;ShD. Tagiyev ,&nbsp;M.R. Marcedula ,&nbsp;C. Demitri ,&nbsp;A.R. Guliyeva ,&nbsp;R.H. Suleymanova","doi":"10.1016/j.carres.2024.109255","DOIUrl":"10.1016/j.carres.2024.109255","url":null,"abstract":"<div><p>Currently, an important ecological problem is environmental pollution and its negative impact on living organisms, the consequences of which are deterioration in general health and the manifestation of various diseases, poisoning, endo- and exotoxicosis. Enterosorption method was proposed as a promising method for removing toxic substances from the living organisms using enterosorbents which can absorb various toxic substances of endogenous and exogenous nature in the lumen of the gastrointestinal tract. It has been proposed to use polymer-containing enterosorbents for eliminating of heavy metals from the organism. The purpose of this research was to synthesize a quaternized derivative of chitosan, specifically N-(2-hydroxybenzyl)-N-ethyl-N-methyl chitosan chloride (Q-CHS). The synthesis of Q-CHS involved the formation of a Schiff base, followed by the quaternization of the amino group of chitosan (CHS). The structures of both pure CHS and quaternized CHS were studied using various physico-chemical methods, including FTIR, NMR, XRD, SEM, DSC and TGA analyses in order to determine the structure and confirm the formation of the final product.</p></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109255"},"PeriodicalIF":2.4,"publicationDate":"2024-08-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142139382","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Stereocontrolled 1,2-trans-arabinofuranosylation in the absence of 2-O-acyl group in glycosyl donor 在糖基供体中没有 2-O-酰基的情况下进行立体控制的 1,2-反式阿拉伯呋喃糖基化反应
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2024-08-30 DOI: 10.1016/j.carres.2024.109252
Polina I. Abronina, Dmitry S. Novikov, Nelly N. Malysheva, Alexander I. Zinin, Alexander O. Chizhov, Leonid O. Kononov
{"title":"Stereocontrolled 1,2-trans-arabinofuranosylation in the absence of 2-O-acyl group in glycosyl donor","authors":"Polina I. Abronina,&nbsp;Dmitry S. Novikov,&nbsp;Nelly N. Malysheva,&nbsp;Alexander I. Zinin,&nbsp;Alexander O. Chizhov,&nbsp;Leonid O. Kononov","doi":"10.1016/j.carres.2024.109252","DOIUrl":"10.1016/j.carres.2024.109252","url":null,"abstract":"<div><p>Stereocontrolled 1,2-<em>trans</em>-α-arabinofuranosylation using polysilylated mono- and disaccharide glycosyl donors was investigated. A complete α-stereoselectivity of 1,2-<em>trans</em>-arabinofuranosylation was found for Ara-β-(1 → 2)-Ara <em>disaccharide</em> glycosyl donors containing five triisopropylsilyl (TIPS) groups with arylthiol (<strong>1</strong>) (as shown in our previous publications) or <em>N</em>-phenyltrifluoroacetimidoyl (<strong>2</strong>) (this work) leaving groups. Conversely, in case of <em>monosaccharide</em> thioglycosides polysilylated with acyclic silyl groups (TIPS, TBDPS), stereoselectivity of glycosylation was lower (α:β = 7–8:1), although the desired α-isomer still dominated. Disaccharide glycosyl donor <strong>2</strong> was successfully used in the synthesis of linear α-(1 → 5)-, β-(1 → 2)-linked hexaarabinofuranoside useful for further preparation of conjugates thereof as antigens valuable for the diagnosis of mycobacterioses.</p></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"544 ","pages":"Article 109252"},"PeriodicalIF":2.4,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142095040","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Galactosylation of glycoconjugates using Pacific oyster β-1,3-galactosyltransferases 利用太平洋牡蛎 β-1,3-半乳糖基转移酶对糖共轭物进行半乳糖基化
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2024-08-28 DOI: 10.1016/j.carres.2024.109254
Zi-Xuan Hu , Yun-Sheng Lyu , Hui-Bo Song, Li Liu, Josef Voglmeir
{"title":"Galactosylation of glycoconjugates using Pacific oyster β-1,3-galactosyltransferases","authors":"Zi-Xuan Hu ,&nbsp;Yun-Sheng Lyu ,&nbsp;Hui-Bo Song,&nbsp;Li Liu,&nbsp;Josef Voglmeir","doi":"10.1016/j.carres.2024.109254","DOIUrl":"10.1016/j.carres.2024.109254","url":null,"abstract":"<div><p>The Pacific oyster (<em>Magallana gigas</em>) exhibits an extensive diversity of <em>N</em>- and O-linked glycoconjugates, offering significant potential for biotechnological applications. Through genomic data mining, we have identified and characterized a suite of β-1,3-galactosyltransferase enzymes, pivotal for the synthesis of glycan structures. Out of ten cloned gene candidates, six enzymes were successfully expressed recombinantly in <em>Escherichia coli</em>. Four of these enzymes exhibited measurable catalytic activity in the transfer of galactose to various acceptor substrates. Notably, MgB3GalT1 demonstrated the highest efficiency, achieving a 91.2 % conversion rate. This enzyme was proficient in glycosylating diverse glycan structures, including Core 2 <em>O</em>-glycans and several di-, tri-, and tetra-antennary complex <em>N</em>-glycan standards. Mass spectrometric analysis confirmed the successful modification of <em>N</em>-glycans. These findings open new approaches for utilizing oyster-derived enzymes in glycan-based therapeutics and molecular glycoengineering, highlighting their utility in synthetic applications and biotechnological advancements.</p></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"544 ","pages":"Article 109254"},"PeriodicalIF":2.4,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142095144","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 regioselectively protected building blocks of benzyl β-d-glucopyranoside 受区域选择性保护的苄基 β-d 吡喃葡萄糖苷结构单元的合成
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2024-08-27 DOI: 10.1016/j.carres.2024.109250
Faranak Pooladian, Anupama Das, Joseph W. Wise, Alexei V. Demchenko
{"title":"Synthesis of regioselectively protected building blocks of benzyl β-d-glucopyranoside","authors":"Faranak Pooladian,&nbsp;Anupama Das,&nbsp;Joseph W. Wise,&nbsp;Alexei V. Demchenko","doi":"10.1016/j.carres.2024.109250","DOIUrl":"10.1016/j.carres.2024.109250","url":null,"abstract":"<div><p>Reported herein is the synthesis of benzyl β-<span>d</span>-glucopyranoside and its derivatives that provide straightforward access to 3,4-branched glycans. Modes to diversify the synthetic intermediates via introduction of various temporary protecting groups have been demonstrated.</p></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"544 ","pages":"Article 109250"},"PeriodicalIF":2.4,"publicationDate":"2024-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142095142","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Enzymatic hydrolysis method for development of low glycemic index rice flour from temperate grown rice (var. Jehlum): Numerical optimization, rheological and spectroscopic characteristics 用酶水解方法从温带大米(Jehlum 变种)中提取低血糖指数米粉:数值优化、流变学和光谱特性
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2024-08-27 DOI: 10.1016/j.carres.2024.109248
Tawheed Amin , H.R. Naik , Syed Zameer Hussain , Omar Bashir , Sajad Ahamd Rather , Sadaf Naaz , Sobiya Manzoor , S.A. Mir , Hilal A. Makroo , Akhoon Asrar Bashir , Shahnaz Mufti , Tariq Ahmad Ganaie , Immad A. Shah
{"title":"Enzymatic hydrolysis method for development of low glycemic index rice flour from temperate grown rice (var. Jehlum): Numerical optimization, rheological and spectroscopic characteristics","authors":"Tawheed Amin ,&nbsp;H.R. Naik ,&nbsp;Syed Zameer Hussain ,&nbsp;Omar Bashir ,&nbsp;Sajad Ahamd Rather ,&nbsp;Sadaf Naaz ,&nbsp;Sobiya Manzoor ,&nbsp;S.A. Mir ,&nbsp;Hilal A. Makroo ,&nbsp;Akhoon Asrar Bashir ,&nbsp;Shahnaz Mufti ,&nbsp;Tariq Ahmad Ganaie ,&nbsp;Immad A. Shah","doi":"10.1016/j.carres.2024.109248","DOIUrl":"10.1016/j.carres.2024.109248","url":null,"abstract":"<div><p>This study aimed at optimizing process protocols for development of low glycemic index (GI) rice flour (LGIRF) by employing enzymatic hydrolysis method using central composite rotatable design (CCRD). LGIRF was evaluated for pasting, farinographic, spectroscopic and microbiological attributes. Independent variables for optimization included concentrations of α-amylase (0.02–0.12 %), glucoamylase (0.02–0.24 %), as well as the incubation temperature (55–80°C). Resistant starch (RS), glycemic index (GI) and glycemic load (GL) were investigated as response variables. The optimum conditions for development of LGIRF with better quality were- α-amylase concentration of 0.040 %, glucoamylase concentration of 0.070 % and an incubation temperature of 60 °C. The results of mineral analysis revealed significantly (p &lt; 0.05) lower levels of boron, potassium, zinc, phosphorus, magnesium, and manganese in LGIRF, while iron and copper were significantly higher. The viscosity profile as evident from pasting profile and farinographic characteristics of LGIRF were significantly (p &lt; 0.05) lower than native rice flour. <sup>1</sup>H NMR and <sup>13</sup>C NMR spectroscopic studies showed an increase in flexible starch segments and a decrease in amorphous portion of starch LGIRF, along with chemical shift alterations in carbons 1 and 4. Free fatty acids and total plate count were significantly (p &lt; 0.05) higher in LGIRF although was within limits.</p></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"544 ","pages":"Article 109248"},"PeriodicalIF":2.4,"publicationDate":"2024-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142117356","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Evaluation of Kochetkov Hemiaminal hydrolysis under acidic, alkaline, and neutral conditions 在酸性、碱性和中性条件下对 Kochetkov Hemiaminal水解作用的评估
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2024-08-27 DOI: 10.1016/j.carres.2024.109253
Julie A. Talbert, Steven D. Townsend
{"title":"Evaluation of Kochetkov Hemiaminal hydrolysis under acidic, alkaline, and neutral conditions","authors":"Julie A. Talbert,&nbsp;Steven D. Townsend","doi":"10.1016/j.carres.2024.109253","DOIUrl":"10.1016/j.carres.2024.109253","url":null,"abstract":"<div><p>The most common precursors to synthetic glycoproteins are reducing end glycosyl amines. To afford these amines, a carbohydrate is reacted with an excess of an ammonia source to yield the β-anomer, exclusively, in a reaction known as the Kochetkov amination. Although this process is the state-of-the-art method to synthesize non-functionalized, β-amino (βA) glycans, misconceptions surrounding the stability of these amines has limited their use in subsequent reactions. Here, we investigated the stability of seven amino sugars in the neutral, acidic, and basic conditions they would be subject to in common reactions using amines. In neutral and basic conditions, the amino sugars proved relatively stable with the fastest time to 50% hydrolysis being four days for only one carbohydrate. However, acidic conditions promoted rapid hydrolysis, with all amino sugars reaching over 97% hydrolysis within 2 h. Finally, we performed a bioconjugation using fluorescein isothiocyanate and βA-difucosyllactose, revealing sufficient stability of the amino product for a successful subsequent reaction.</p></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"544 ","pages":"Article 109253"},"PeriodicalIF":2.4,"publicationDate":"2024-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0008621524002325/pdfft?md5=7948b44ca29fa44e25fce27162053ed9&pid=1-s2.0-S0008621524002325-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142095145","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Interglycosidic C5–C6 rotamer distributions of alkyl O-rutinosides 烷基 O-芸香糖苷的糖苷间 C5-C6 转子分布
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2024-08-26 DOI: 10.1016/j.carres.2024.109251
Dhwani Mehta, Carlos A. Sanhueza
{"title":"Interglycosidic C5–C6 rotamer distributions of alkyl O-rutinosides","authors":"Dhwani Mehta,&nbsp;Carlos A. Sanhueza","doi":"10.1016/j.carres.2024.109251","DOIUrl":"10.1016/j.carres.2024.109251","url":null,"abstract":"<div><p>The conformational study of carbohydrates is critical to understand the molecular recognition mechanisms underlying their biological functions. Moreover, the systematic study of their conformational patterns can unlock useful tools to design optimized glycomimetics and drug candidates. Using nuclear magnetic resonance, we studied the interglycosidic rotamer equilibria of ester-protected and deprotected alkyl <em>O</em>-rutinosides (α-L-Rha(1,6)β-D-GlcOR). In the protected series, the equilibrium about the C5–C6 bond distributes among the three possible rotamers <em>gg</em>, <em>gt</em>, and <em>tg</em>, being <em>gt</em> the predominant conformer. In these series, the flexibility about C5–C6 shows a marked dependency on the aglycone's structure, where the increase on the aglycone's volume leads to a progressive increment on the tg contributions at the expense of <em>gt</em>, with <em>gg</em> remaining practically constant along the series. The removal of the protective groups results in rutinosides displaying an equilibrium equally distributed between <em>gg</em> and <em>gt</em> with no tg contributions regardless of the aglycone's structure.</p></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"544 ","pages":"Article 109251"},"PeriodicalIF":2.4,"publicationDate":"2024-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142088829","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 the pyruvic acid acetal containing tetrasaccharide repeating unit corresponding to the K82 capsular polysaccharide of Acinetobacter baumannii LUH5534 strain 合成与鲍曼不动杆菌 LUH5534 菌株 K82 胶囊多糖相对应的含丙酮酸缩醛的四糖重复单元
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2024-08-24 DOI: 10.1016/j.carres.2024.109249
Samim Sahaji, Puja Bag, Anup Kumar Misra
{"title":"Synthesis of the pyruvic acid acetal containing tetrasaccharide repeating unit corresponding to the K82 capsular polysaccharide of Acinetobacter baumannii LUH5534 strain","authors":"Samim Sahaji,&nbsp;Puja Bag,&nbsp;Anup Kumar Misra","doi":"10.1016/j.carres.2024.109249","DOIUrl":"10.1016/j.carres.2024.109249","url":null,"abstract":"<div><p>An efficient synthetic strategy has been developed to achieve a pyruvic acid acetal containing tetrasaccharide repeating unit corresponding to the K82 capsular polysaccharide of <em>Acinetobacter baumannii</em> LUH5534 strain in very good yield. The synthetic scheme involves the use of suitably functionalized monosaccharide thioglycosides as glycosyl donors and a combination of <em>N</em>-iodosuccinimide (NIS) and trimethylsilyl trifluoromethanesulfonate (TMSOTf) as thiophilic glycosylation activator to furnish satisfactory yield of the products with appropriate stereochemistry at the glycosidic linkages. Incorporation of the (<em>R</em>)-pyruvic acid acetal in the <span>d</span>-galactose moiety was achieved in very good yield by the treatment of the diol derivative with methyl 2,2-bis(<em>p</em>-methylphenylthio)propionate in the presence of a combination of NIS and triflic acid.</p></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"544 ","pages":"Article 109249"},"PeriodicalIF":2.4,"publicationDate":"2024-08-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142076989","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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