以抗坏血酸棕榈酸钠盐（Asp-Na）为绿色助催化剂，微波辅助合成左旋葡聚糖三唑糖缀合物

IF 2.4 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research Pub Date : 2025-05-10 DOI:10.1016/j.carres.2025.109511

Nishant Pandey , Pratibha Dwivedi , Alisha , Bhuwan B. Mishra

{"title":"以抗坏血酸棕榈酸钠盐（Asp-Na）为绿色助催化剂，微波辅助合成左旋葡聚糖三唑糖缀合物","authors":"Nishant Pandey , Pratibha Dwivedi , Alisha , Bhuwan B. Mishra","doi":"10.1016/j.carres.2025.109511","DOIUrl":null,"url":null,"abstract":"<div><div>Ascorbyl palmitate sodium salt (Asp-Na) <strong>2</strong> has been found to be a highly effective co-catalyst in copper catalyzed azide-alkyne cycloaddition (CuAAC) reactions under microwave (MW) condition. This co-catalyst provides a more cost-efficient option compared to sodium ascorbate by reducing the stoichiometric amount of ascorbic acid required for the CuAAC reaction. With its palmitate side chain, Asp-Na <strong>2</strong> acts as a surfactant by improving the solubility of substrates, particularly the lipophilic compounds. Notably, it can be obtained in high purity by semi-synthesis from non-edible oils, aligning with the sustainable practices. Application of <strong>2</strong> in CuAAC reaction of levoglucosan based terminal alkyne <strong>(3)</strong> and <em>azido</em>-sugars <strong>(4)</strong> furnished the corresponding triazolyl glycoconjugates <strong>(5)</strong> in yields ranging between 70 and 90 %.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"553 ","pages":"Article 109511"},"PeriodicalIF":2.4000,"publicationDate":"2025-05-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Microwave-assisted click synthesis of levoglucosan triazolyl glycoconjugates using ascorbyl palmitate sodium salt (Asp-Na) as a green Co-catalyst\",\"authors\":\"Nishant Pandey , Pratibha Dwivedi , Alisha , Bhuwan B. Mishra\",\"doi\":\"10.1016/j.carres.2025.109511\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Ascorbyl palmitate sodium salt (Asp-Na) <strong>2</strong> has been found to be a highly effective co-catalyst in copper catalyzed azide-alkyne cycloaddition (CuAAC) reactions under microwave (MW) condition. This co-catalyst provides a more cost-efficient option compared to sodium ascorbate by reducing the stoichiometric amount of ascorbic acid required for the CuAAC reaction. With its palmitate side chain, Asp-Na <strong>2</strong> acts as a surfactant by improving the solubility of substrates, particularly the lipophilic compounds. Notably, it can be obtained in high purity by semi-synthesis from non-edible oils, aligning with the sustainable practices. Application of <strong>2</strong> in CuAAC reaction of levoglucosan based terminal alkyne <strong>(3)</strong> and <em>azido</em>-sugars <strong>(4)</strong> furnished the corresponding triazolyl glycoconjugates <strong>(5)</strong> in yields ranging between 70 and 90 %.</div></div>\",\"PeriodicalId\":9415,\"journal\":{\"name\":\"Carbohydrate Research\",\"volume\":\"553 \",\"pages\":\"Article 109511\"},\"PeriodicalIF\":2.4000,\"publicationDate\":\"2025-05-10\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Carbohydrate Research\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0008621525001375\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Carbohydrate Research","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0008621525001375","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}

引用次数: 0

摘要

抗坏血酸棕榈酸钠盐（Asp-Na） 2是微波条件下铜催化叠氮-炔环加成（CuAAC）反应的高效助催化剂。与抗坏血酸钠相比，这种助催化剂通过减少CuAAC反应所需的抗坏血酸的化学计量量，提供了一种更具成本效益的选择。凭借其棕榈酸侧链，Asp-Na - 2作为表面活性剂，通过改善底物的溶解度，特别是亲脂性化合物。值得注意的是，它可以通过非食用油的半合成获得高纯度，符合可持续实践。将2应用于左旋葡聚糖末端炔(3)和叠氮糖(4)的CuAAC反应中，得到相应的三唑基糖缀合物(5)，收率在70% ~ 90%之间。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

Microwave-assisted click synthesis of levoglucosan triazolyl glycoconjugates using ascorbyl palmitate sodium salt (Asp-Na) as a green Co-catalyst

Ascorbyl palmitate sodium salt (Asp-Na) 2 has been found to be a highly effective co-catalyst in copper catalyzed azide-alkyne cycloaddition (CuAAC) reactions under microwave (MW) condition. This co-catalyst provides a more cost-efficient option compared to sodium ascorbate by reducing the stoichiometric amount of ascorbic acid required for the CuAAC reaction. With its palmitate side chain, Asp-Na 2 acts as a surfactant by improving the solubility of substrates, particularly the lipophilic compounds. Notably, it can be obtained in high purity by semi-synthesis from non-edible oils, aligning with the sustainable practices. Application of 2 in CuAAC reaction of levoglucosan based terminal alkyne (3) and azido-sugars (4) furnished the corresponding triazolyl glycoconjugates (5) in yields ranging between 70 and 90 %.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Carbohydrate Research 化学-生化与分子生物学

CiteScore

5.00

自引率

3.20%

发文量

183

审稿时长

3.6 weeks

期刊介绍： Carbohydrate Research publishes reports of original research in the following areas of carbohydrate science: action of enzymes, analytical chemistry, biochemistry (biosynthesis, degradation, structural and functional biochemistry, conformation, molecular recognition, enzyme mechanisms, carbohydrate-processing enzymes, including glycosidases and glycosyltransferases), chemical synthesis, isolation of natural products, physicochemical studies, reactions and their mechanisms, the study of structures and stereochemistry, and technological aspects. Papers on polysaccharides should have a "molecular" component; that is a paper on new or modified polysaccharides should include structural information and characterization in addition to the usual studies of rheological properties and the like. A paper on a new, naturally occurring polysaccharide should include structural information, defining monosaccharide components and linkage sequence. Papers devoted wholly or partly to X-ray crystallographic studies, or to computational aspects (molecular mechanics or molecular orbital calculations, simulations via molecular dynamics), will be considered if they meet certain criteria. For computational papers the requirements are that the methods used be specified in sufficient detail to permit replication of the results, and that the conclusions be shown to have relevance to experimental observations - the authors'' own data or data from the literature. Specific directions for the presentation of X-ray data are given below under Results and "discussion".