Alex Ann, Steven Truong, Jiwani Peters, David R. Mootoo
{"title":"alpha-Gal C-二糖的合成","authors":"Alex Ann, Steven Truong, Jiwani Peters, David R. Mootoo","doi":"10.1016/j.bmc.2024.117903","DOIUrl":null,"url":null,"abstract":"<div><p>The synthesis of C-disaccharides of α-<span>d</span>-galactopyranosyl-(1 → 3)-<span>d</span>-galactopyranose (α-Gal), potential tools for studying the biology of α-Gal glycans, is described. The synthetic strategy, centers on the reaction of two easily available precursors 1,2-O-isopropylidene-<span>d</span>-glyceraldehyde and an α-C-glactosyl-<em>E</em>-crotylboronate, which affords a mixture of two diastereomeric anti-crotylation products. The stereoselectivity of this reaction was controlled with (<em>R</em>)- and (S)-TRIP catalysts, and the appropriate diastereomer was transformed to C-linked disaccharides of α-Gal, in which the aglycone segment comprised O-, C- and S-glycoside entities that can enable glycoconjugate synthesis.</p></div>","PeriodicalId":255,"journal":{"name":"Bioorganic & Medicinal Chemistry","volume":"112 ","pages":"Article 117903"},"PeriodicalIF":3.3000,"publicationDate":"2024-08-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of alpha-Gal C-disaccharides\",\"authors\":\"Alex Ann, Steven Truong, Jiwani Peters, David R. Mootoo\",\"doi\":\"10.1016/j.bmc.2024.117903\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>The synthesis of C-disaccharides of α-<span>d</span>-galactopyranosyl-(1 → 3)-<span>d</span>-galactopyranose (α-Gal), potential tools for studying the biology of α-Gal glycans, is described. The synthetic strategy, centers on the reaction of two easily available precursors 1,2-O-isopropylidene-<span>d</span>-glyceraldehyde and an α-C-glactosyl-<em>E</em>-crotylboronate, which affords a mixture of two diastereomeric anti-crotylation products. The stereoselectivity of this reaction was controlled with (<em>R</em>)- and (S)-TRIP catalysts, and the appropriate diastereomer was transformed to C-linked disaccharides of α-Gal, in which the aglycone segment comprised O-, C- and S-glycoside entities that can enable glycoconjugate synthesis.</p></div>\",\"PeriodicalId\":255,\"journal\":{\"name\":\"Bioorganic & Medicinal Chemistry\",\"volume\":\"112 \",\"pages\":\"Article 117903\"},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2024-08-31\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Bioorganic & Medicinal Chemistry\",\"FirstCategoryId\":\"3\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0968089624003171\",\"RegionNum\":3,\"RegionCategory\":\"医学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Bioorganic & Medicinal Chemistry","FirstCategoryId":"3","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0968089624003171","RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
The synthesis of C-disaccharides of α-d-galactopyranosyl-(1 → 3)-d-galactopyranose (α-Gal), potential tools for studying the biology of α-Gal glycans, is described. The synthetic strategy, centers on the reaction of two easily available precursors 1,2-O-isopropylidene-d-glyceraldehyde and an α-C-glactosyl-E-crotylboronate, which affords a mixture of two diastereomeric anti-crotylation products. The stereoselectivity of this reaction was controlled with (R)- and (S)-TRIP catalysts, and the appropriate diastereomer was transformed to C-linked disaccharides of α-Gal, in which the aglycone segment comprised O-, C- and S-glycoside entities that can enable glycoconjugate synthesis.
期刊介绍:
Bioorganic & Medicinal Chemistry provides an international forum for the publication of full original research papers and critical reviews on molecular interactions in key biological targets such as receptors, channels, enzymes, nucleotides, lipids and saccharides.
The aim of the journal is to promote a better understanding at the molecular level of life processes, and living organisms, as well as the interaction of these with chemical agents. A special feature will be that colour illustrations will be reproduced at no charge to the author, provided that the Editor agrees that colour is essential to the information content of the illustration in question.