{"title":"Efficient heterogeneous synthesis of nucleophilic carboxymethyl hydrazides of polysaccharides","authors":"Hendryk Würfel, Annett Pfeifer, Thomas Heinze","doi":"10.1002/bip.23574","DOIUrl":null,"url":null,"abstract":"<p>Nucleophilic moieties in polysaccharides (PS) with distinct higher reactivity compared with the hydroxy group are interesting for sustainable applications in chemistry, medicine, and pharmacy. An efficient heterogeneous method for the formation of such nucleophilic PS is described. Employing alcohols as slurry medium, protonated carboxymethyl (CM) PS and hydrazine hydrate are allowed to react at elevated temperatures. The CM derivatives of starch and pullulan can be transformed almost quantitatively to the corresponding hydrazides. The reaction is less efficient for CM dextrans and CM xylans. As slurry media, 2-propanol and ethanol were probed, and the results are compared with a homogeneous procedure performed in water. Overall, the heterogeneous procedure is superior compared with the homogeneous route. 2-Propanol is the best slurry medium investigated yielding PS hydrazides with the highest nitrogen content.</p>","PeriodicalId":8866,"journal":{"name":"Biopolymers","volume":"115 3","pages":""},"PeriodicalIF":3.2000,"publicationDate":"2024-03-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Biopolymers","FirstCategoryId":"99","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/bip.23574","RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
引用次数: 0
Abstract
Nucleophilic moieties in polysaccharides (PS) with distinct higher reactivity compared with the hydroxy group are interesting for sustainable applications in chemistry, medicine, and pharmacy. An efficient heterogeneous method for the formation of such nucleophilic PS is described. Employing alcohols as slurry medium, protonated carboxymethyl (CM) PS and hydrazine hydrate are allowed to react at elevated temperatures. The CM derivatives of starch and pullulan can be transformed almost quantitatively to the corresponding hydrazides. The reaction is less efficient for CM dextrans and CM xylans. As slurry media, 2-propanol and ethanol were probed, and the results are compared with a homogeneous procedure performed in water. Overall, the heterogeneous procedure is superior compared with the homogeneous route. 2-Propanol is the best slurry medium investigated yielding PS hydrazides with the highest nitrogen content.
与羟基相比,多糖(PS)中的亲核分子具有更高的反应活性,可持续应用于化学、医学和药学领域。本文介绍了一种形成此类亲核多糖的高效异构方法。使用醇类作为淤浆介质,质子化的羧甲基(CM)PS 和水合肼在高温下发生反应。淀粉和拉普兰的 CM 衍生物几乎可以定量地转化为相应的酰肼。对于 CM 右旋糖酐和 CM 木聚糖来说,该反应的效率较低。研究人员将 2-丙醇和乙醇作为浆料介质,并将结果与在水中进行的均相反应进行了比较。总体而言,异构过程优于均相过程。2 丙醇是所研究的最佳淤浆介质,可产生含氮量最高的 PS 联酰肼。
期刊介绍:
Founded in 1963, Biopolymers publishes strictly peer-reviewed papers examining naturally occurring and synthetic biological macromolecules. By including experimental and theoretical studies on the fundamental behaviour as well as applications of biopolymers, the journal serves the interdisciplinary biochemical, biophysical, biomaterials and biomedical research communities.