Jun Wang , Qiang Fu , Xiaoxiao Wang , Honglin Zhang , Daoqiang Lu , Xiu Wang , Riwang Li , Dahai Liu
{"title":"一种使壳聚糖化学选择性修饰的替代胺保护策略","authors":"Jun Wang , Qiang Fu , Xiaoxiao Wang , Honglin Zhang , Daoqiang Lu , Xiu Wang , Riwang Li , Dahai Liu","doi":"10.1016/j.carbpol.2025.124511","DOIUrl":null,"url":null,"abstract":"<div><div>The trifluoroacetyl group is a widely used and easily removable amino-protecting group, making it an ideal choice for protecting the amino groups of chitosan. However, current methods for trifluoroacetylation of chitosan suffer from low reaction efficiency and limited modification degrees, posing a persistent challenge for achieving complete <em>N</em>-trifluoroacetylation. In this study, a simple and efficient method for preparing amino-protected chitosan, specifically <em>N</em>-trifluoroacetyl chitosan, is presented. The process is carried out in a homogeneous solution at room temperature, without the need for stringent anhydrous or oxygen-free conditions, and involves a brief reaction time. <em>N</em>-trifluoroacetyl chitosan exhibits good solubility in organic solvents, enabling homogeneous reactions with reagents such as enol ethers or <em>t</em>-butyldimethylchlorosilane. Furthermore, the protecting group can be easily removed under mild conditions. This method for amino group protection in chitosan offers a convenient approach for subsequent modifications.</div></div>","PeriodicalId":261,"journal":{"name":"Carbohydrate Polymers","volume":"371 ","pages":"Article 124511"},"PeriodicalIF":12.5000,"publicationDate":"2025-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"An alternative amine protection strategy for chitosan enabling chemoselective modifications\",\"authors\":\"Jun Wang , Qiang Fu , Xiaoxiao Wang , Honglin Zhang , Daoqiang Lu , Xiu Wang , Riwang Li , Dahai Liu\",\"doi\":\"10.1016/j.carbpol.2025.124511\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>The trifluoroacetyl group is a widely used and easily removable amino-protecting group, making it an ideal choice for protecting the amino groups of chitosan. However, current methods for trifluoroacetylation of chitosan suffer from low reaction efficiency and limited modification degrees, posing a persistent challenge for achieving complete <em>N</em>-trifluoroacetylation. In this study, a simple and efficient method for preparing amino-protected chitosan, specifically <em>N</em>-trifluoroacetyl chitosan, is presented. The process is carried out in a homogeneous solution at room temperature, without the need for stringent anhydrous or oxygen-free conditions, and involves a brief reaction time. <em>N</em>-trifluoroacetyl chitosan exhibits good solubility in organic solvents, enabling homogeneous reactions with reagents such as enol ethers or <em>t</em>-butyldimethylchlorosilane. Furthermore, the protecting group can be easily removed under mild conditions. This method for amino group protection in chitosan offers a convenient approach for subsequent modifications.</div></div>\",\"PeriodicalId\":261,\"journal\":{\"name\":\"Carbohydrate Polymers\",\"volume\":\"371 \",\"pages\":\"Article 124511\"},\"PeriodicalIF\":12.5000,\"publicationDate\":\"2025-10-09\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Carbohydrate Polymers\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0144861725012950\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, APPLIED\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Carbohydrate Polymers","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0144861725012950","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
An alternative amine protection strategy for chitosan enabling chemoselective modifications
The trifluoroacetyl group is a widely used and easily removable amino-protecting group, making it an ideal choice for protecting the amino groups of chitosan. However, current methods for trifluoroacetylation of chitosan suffer from low reaction efficiency and limited modification degrees, posing a persistent challenge for achieving complete N-trifluoroacetylation. In this study, a simple and efficient method for preparing amino-protected chitosan, specifically N-trifluoroacetyl chitosan, is presented. The process is carried out in a homogeneous solution at room temperature, without the need for stringent anhydrous or oxygen-free conditions, and involves a brief reaction time. N-trifluoroacetyl chitosan exhibits good solubility in organic solvents, enabling homogeneous reactions with reagents such as enol ethers or t-butyldimethylchlorosilane. Furthermore, the protecting group can be easily removed under mild conditions. This method for amino group protection in chitosan offers a convenient approach for subsequent modifications.
期刊介绍:
Carbohydrate Polymers stands as a prominent journal in the glycoscience field, dedicated to exploring and harnessing the potential of polysaccharides with applications spanning bioenergy, bioplastics, biomaterials, biorefining, chemistry, drug delivery, food, health, nanotechnology, packaging, paper, pharmaceuticals, medicine, oil recovery, textiles, tissue engineering, wood, and various aspects of glycoscience.
The journal emphasizes the central role of well-characterized carbohydrate polymers, highlighting their significance as the primary focus rather than a peripheral topic. Each paper must prominently feature at least one named carbohydrate polymer, evident in both citation and title, with a commitment to innovative research that advances scientific knowledge.