Reaction of sugar oxazolines with primary amines

[Display omitted] •Sugar oxazolines react with primary amines to form imidazolines.•These imidazolines are easily dehydrated to form imidazoles.•This is a simple way to attach a glycan on peptides and proteins. Sugar oxazolines, obtained by a dehydration reaction of 2-acetylamino pyranosides, reacte...

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Bibliographic Details
Published in:Tetrahedron letters 2016-12, Vol.57 (49), p.5446-5448
Main Authors: Suda, Minoru, Sumiyoshi, Wataru, Kinoshita, Takashi, Ohno, Shoko
Format: Article
Language:English
Subjects:
Glycation
Imidazoline
Primary amine
Sugar oxazoline
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Summary:[Display omitted] •Sugar oxazolines react with primary amines to form imidazolines.•These imidazolines are easily dehydrated to form imidazoles.•This is a simple way to attach a glycan on peptides and proteins. Sugar oxazolines, obtained by a dehydration reaction of 2-acetylamino pyranosides, reacted with primary amines in water to produce sugar imidazolines, which, when heated in water, were converted to sugar imidazoles by a dehydration reaction. The structures of these rather unexpected reaction products were determined by spectroscopic data. This offers a simple process to introduce a glycan onto peptides, proteins, and other biologically important compounds.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.10.074