Block synthesis of Forssman pentasaccharide GalNAcα1-3GalNAcβ1-3Galα1-4Galβ1-4Glcβ in the form of 3-aminopropyl glycoside

IF 2.5 3区 化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY Carbohydrate Research Pub Date : 2024-12-28 DOI:10.1016/j.carres.2024.109370
Inna S. Popova , Marina A. Sablina , Ivan M. Ryzhov , Darya O. Anisimova , Tatiana V. Ovchinnikova , Tatiana V. Tyrtysh , Elena Yu. Korchagina , Alexander O. Chizhov , Alexander S. Paramonov , Nicolai V. Bovin
{"title":"Block synthesis of Forssman pentasaccharide GalNAcα1-3GalNAcβ1-3Galα1-4Galβ1-4Glcβ in the form of 3-aminopropyl glycoside","authors":"Inna S. Popova ,&nbsp;Marina A. Sablina ,&nbsp;Ivan M. Ryzhov ,&nbsp;Darya O. Anisimova ,&nbsp;Tatiana V. Ovchinnikova ,&nbsp;Tatiana V. Tyrtysh ,&nbsp;Elena Yu. Korchagina ,&nbsp;Alexander O. Chizhov ,&nbsp;Alexander S. Paramonov ,&nbsp;Nicolai V. Bovin","doi":"10.1016/j.carres.2024.109370","DOIUrl":null,"url":null,"abstract":"<div><div>A total chemical synthesis of spacer-armed Forssman pentasaccharide is reported. The choice of the 2(donor) + 3(acceptor) block scheme, the optimal combination of a limited number of simple protecting groups and the sequence of deprotection steps allowed to achieve the high yield and stereoselectivity of glycosylation and to avoid losses during deprotection. The target pentasaccharide was obtained in a 10-mg scale. <sup>1</sup>H and <sup>13</sup>C NMR spectra of the Forssman pentasaccharide were completely assigned with the use of various 2D-NMR experiments.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"Article 109370"},"PeriodicalIF":2.5000,"publicationDate":"2024-12-28","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/S0008621524003495","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

Abstract

A total chemical synthesis of spacer-armed Forssman pentasaccharide is reported. The choice of the 2(donor) + 3(acceptor) block scheme, the optimal combination of a limited number of simple protecting groups and the sequence of deprotection steps allowed to achieve the high yield and stereoselectivity of glycosylation and to avoid losses during deprotection. The target pentasaccharide was obtained in a 10-mg scale. 1H and 13C NMR spectra of the Forssman pentasaccharide were completely assigned with the use of various 2D-NMR experiments.

Abstract Image

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
阻断合成3-氨基丙基糖苷形式的Forssman五糖galna α1- 3galna β1- 3gal α1- 4gal β1- 4glc β。
报道了间隔臂Forssman五糖的全化学合成。2(供体)+ 3(受体)阻滞方案的选择,有限数量的简单保护基团的最佳组合和脱保护步骤的顺序可以实现糖基化的高收率和立体选择性,并避免脱保护过程中的损失。目标五糖以10mg的比例得到。通过各种2D-NMR实验,对Forssman五糖的1H和13C NMR谱进行了完整的分配。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 去求助
来源期刊
Carbohydrate Research
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".
期刊最新文献
Influence of N- and O-glycosylation on structural properties and biological activity of a C-terminal LL-37 fragment. Synthetic strategies for the modification of primary hydroxyl and carboxyl groups of Gellan towards the development of advanced biomaterials. Synthetic studies towards cryptolaevilactone M from d-glucose. Effect of bacterial cellulose crystal form on its oil-water separation. Sustainable nanogold-cellulose composites: Green synthesis, emerging applications and future aspects.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:604180095
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1