Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations
Synthetic heteroglycoclusters are being subjected to increasing interest due to their potential to serve as selective ligands for carbohydrate-binding proteins. In this paper, we describe an expedient strategy to prepare cyclopeptides displaying well-defined distributions and combinations of carbohy...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2012-03-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.8.47 |
| _version_ | 1831693318501695488 |
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| author | Baptiste Thomas Michele Fiore Isabelle Bossu Pascal Dumy Olivier Renaudet |
| author_facet | Baptiste Thomas Michele Fiore Isabelle Bossu Pascal Dumy Olivier Renaudet |
| author_sort | Baptiste Thomas |
| collection | DOAJ |
| description | Synthetic heteroglycoclusters are being subjected to increasing interest due to their potential to serve as selective ligands for carbohydrate-binding proteins. In this paper, we describe an expedient strategy to prepare cyclopeptides displaying well-defined distributions and combinations of carbohydrates. By using both oxime ligation and copper(I)-catalyzed alkyne–azide cycloaddition, two series of compounds bearing binary combinations of αMan, αFuc or βLac in an overall tetravalent presentation, and either 2:2 or 3:1 relative proportions, have been prepared. |
| first_indexed | 2024-12-20T12:12:11Z |
| format | Article |
| id | doaj.art-16f5b51a578d4e3fb61432c3f4efaa02 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-20T12:12:11Z |
| publishDate | 2012-03-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-16f5b51a578d4e3fb61432c3f4efaa022022-12-21T19:41:14ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972012-03-018142142710.3762/bjoc.8.471860-5397-8-47Synthesis of heteroglycoclusters by using orthogonal chemoselective ligationsBaptiste Thomas0Michele Fiore1Isabelle Bossu2Pascal Dumy3Olivier Renaudet4Département de Chimie Moléculaire, UMR-CNRS 5250 & ICMG FR 2607, Université Joseph Fourier, PB 53, 38041 Grenoble Cedex 9, FranceDépartement de Chimie Moléculaire, UMR-CNRS 5250 & ICMG FR 2607, Université Joseph Fourier, PB 53, 38041 Grenoble Cedex 9, FranceDépartement de Chimie Moléculaire, UMR-CNRS 5250 & ICMG FR 2607, Université Joseph Fourier, PB 53, 38041 Grenoble Cedex 9, FranceDépartement de Chimie Moléculaire, UMR-CNRS 5250 & ICMG FR 2607, Université Joseph Fourier, PB 53, 38041 Grenoble Cedex 9, FranceDépartement de Chimie Moléculaire, UMR-CNRS 5250 & ICMG FR 2607, Université Joseph Fourier, PB 53, 38041 Grenoble Cedex 9, FranceSynthetic heteroglycoclusters are being subjected to increasing interest due to their potential to serve as selective ligands for carbohydrate-binding proteins. In this paper, we describe an expedient strategy to prepare cyclopeptides displaying well-defined distributions and combinations of carbohydrates. By using both oxime ligation and copper(I)-catalyzed alkyne–azide cycloaddition, two series of compounds bearing binary combinations of αMan, αFuc or βLac in an overall tetravalent presentation, and either 2:2 or 3:1 relative proportions, have been prepared.https://doi.org/10.3762/bjoc.8.47chemoselective ligationclick chemistrycyclopeptideheteroglycoclusteroxime |
| spellingShingle | Baptiste Thomas Michele Fiore Isabelle Bossu Pascal Dumy Olivier Renaudet Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations Beilstein Journal of Organic Chemistry chemoselective ligation click chemistry cyclopeptide heteroglycocluster oxime |
| title | Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations |
| title_full | Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations |
| title_fullStr | Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations |
| title_full_unstemmed | Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations |
| title_short | Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations |
| title_sort | synthesis of heteroglycoclusters by using orthogonal chemoselective ligations |
| topic | chemoselective ligation click chemistry cyclopeptide heteroglycocluster oxime |
| url | https://doi.org/10.3762/bjoc.8.47 |
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