Two-step conversion of unprotected oligosaccharides to generate bioorthogonal oligosaccharide tool compounds

Oligosaccharides have valuable effects in biological systems, but their complex nature makes them difficult to convert into chemical tools. We have developed a two-step conversion of unprotected oligosaccharides that is highly amenable to generating a variety of complex oligosaccharide tool compound...

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Bibliographic Details
Published inMethodsX Vol. 7; p. 100996
Main Authors Chambers, Schuyler A., Townsend, Steven D.
Format Journal Article
LanguageEnglish
Published Elsevier B.V 01.01.2020
Elsevier
Subjects
Bioorthogonal probes
Chemistry
Complex carbohydrates
Facile synthesis
Two-step conversion of deprotected oligosaccharides to generate bioorthogonal tools for chemical biology applications
Facile synthesis
Complex carbohydrates
Two-step conversion of deprotected oligosaccharides to generate bioorthogonal tools for chemical biology applications
Bioorthogonal probes
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Summary:Oligosaccharides have valuable effects in biological systems, but their complex nature makes them difficult to convert into chemical tools. We have developed a two-step conversion of unprotected oligosaccharides that is highly amenable to generating a variety of complex oligosaccharide tool compounds. This sequence features an optimized Kochetkov amination procedure and subsequent amide coupling. With these simple synthetic conversions, the creation of novel bioorthogonal carbohydrate probes becomes easily accessible and new avenues for chemical biology may be opened.•Optimized Kochetkov amination procedure for complex oligosaccharides.•Highly versatile amide coupling for facile probe synthesis. [Display omitted]
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ISSN:2215-0161
2215-0161
DOI:10.1016/j.mex.2020.100996