Literature DB >> 25084507

Side reactions with 2,2,2-trichloroethoxysulfates during the synthesis of glycans.

Kenya Matsushita1, Yuta Sato2, Shinji Funamoto3, Jun-ichi Tamura4.   

Abstract

Protected sulfate groups may be used as an alternative tool to provide sulfate esters at hydroxyl and amino groups, particularly on complex glycans. We examined 2,2,2-trichloroethoxysulfation at the mono-, di-, and trihydroxyl groups of saccharide moieties to show regioselective sulfation. We found some side reactions including inter- and intramolecular nucleophilic reactions with 2,2,2-trichloroethoxysulfates.
Copyright © 2014 Elsevier Ltd. All rights reserved.

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Keywords:  2,2,2-Trichloroethoxysulfate; Glycan synthesis; Intramolecular attack; Protected sulfate; Sulfated oligosaccharide

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Year:  2014        PMID: 25084507     DOI: 10.1016/j.carres.2014.05.012

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN: 0008-6215            Impact factor:   2.104


  1 in total

1.  Chemical synthesis of human syndecan-4 glycopeptide bearing O-, N-sulfation and multiple aspartic acids for probing impacts of the glycan chain and the core peptide on biological functions.

Authors:  Weizhun Yang; Yigitcan Eken; Jicheng Zhang; Logan Emerson Cole; Sherif Ramadan; Yongmei Xu; Zeren Zhang; Jian Liu; Angela K Wilson; Xuefei Huang
Journal:  Chem Sci       Date:  2020-05-11       Impact factor: 9.825

  1 in total

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