Glycosylation efficiencies on different solid supports using a hydrogenolysis-labile linker

Automated oligosaccharide assembly requires suitable linkers to connect the first monosaccharide to a solid support. A new hydrogenolysis-labile linker that is stable under both acidic and basic conditions was designed, synthesized and coupled to different resins. Glycosylation and cleavage efficien...

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Main Authors: Mayeul Collot, Steffen Eller, Markus Weishaupt, Peter H. Seeberger
Format: Article
Language:English
Published: Beilstein-Institut 2013-01-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
Online Access:https://doi.org/10.3762/bjoc.9.13
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author Mayeul Collot
Steffen Eller
Markus Weishaupt
Peter H. Seeberger
author_facet Mayeul Collot
Steffen Eller
Markus Weishaupt
Peter H. Seeberger
author_sort Mayeul Collot
collection DOAJ
description Automated oligosaccharide assembly requires suitable linkers to connect the first monosaccharide to a solid support. A new hydrogenolysis-labile linker that is stable under both acidic and basic conditions was designed, synthesized and coupled to different resins. Glycosylation and cleavage efficiencies on these functionalized solid supports were investigated, and restrictions for the choice of solid support for oligosaccharide synthesis were found.
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spelling doaj.art-b0456ee9449b4191888481c2ed9bfaa32022-12-21T18:59:26ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972013-01-01919710510.3762/bjoc.9.131860-5397-9-13Glycosylation efficiencies on different solid supports using a hydrogenolysis-labile linkerMayeul Collot0Steffen Eller1Markus Weishaupt2Peter H. Seeberger3Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14776 Potsdam, GermanyDepartment of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14776 Potsdam, GermanyDepartment of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14776 Potsdam, GermanyDepartment of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14776 Potsdam, GermanyAutomated oligosaccharide assembly requires suitable linkers to connect the first monosaccharide to a solid support. A new hydrogenolysis-labile linker that is stable under both acidic and basic conditions was designed, synthesized and coupled to different resins. Glycosylation and cleavage efficiencies on these functionalized solid supports were investigated, and restrictions for the choice of solid support for oligosaccharide synthesis were found.https://doi.org/10.3762/bjoc.9.13glycosylationhydrogenolysislinkersoligosaccharidesresinssolid-phase synthesis
spellingShingle Mayeul Collot
Steffen Eller
Markus Weishaupt
Peter H. Seeberger
Glycosylation efficiencies on different solid supports using a hydrogenolysis-labile linker
Beilstein Journal of Organic Chemistry
glycosylation
hydrogenolysis
linkers
oligosaccharides
resins
solid-phase synthesis
title Glycosylation efficiencies on different solid supports using a hydrogenolysis-labile linker
title_full Glycosylation efficiencies on different solid supports using a hydrogenolysis-labile linker
title_fullStr Glycosylation efficiencies on different solid supports using a hydrogenolysis-labile linker
title_full_unstemmed Glycosylation efficiencies on different solid supports using a hydrogenolysis-labile linker
title_short Glycosylation efficiencies on different solid supports using a hydrogenolysis-labile linker
title_sort glycosylation efficiencies on different solid supports using a hydrogenolysis labile linker
topic glycosylation
hydrogenolysis
linkers
oligosaccharides
resins
solid-phase synthesis
url https://doi.org/10.3762/bjoc.9.13
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AT steffeneller glycosylationefficienciesondifferentsolidsupportsusingahydrogenolysislabilelinker
AT markusweishaupt glycosylationefficienciesondifferentsolidsupportsusingahydrogenolysislabilelinker
AT peterhseeberger glycosylationefficienciesondifferentsolidsupportsusingahydrogenolysislabilelinker