Nucleophilic Catalysis of Carbohydrate Oxime Formation by Anilines

Nucleophilic Catalysis of Carbohydrate Oxime Formation by Anilines

Chemoselective formation of glycoconjugates from unprotected glycans is needed to further develop chemical biology involving glycans. Carbohydrate oxime formation is often slow, and organocatalysis by anilines would be highly promising. Here, we present that carbohydrate oxime formation can be catal...

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Veröffentlicht in:Journal of organic chemistry 2010-03, Vol.75 (5), p.1752-1755
Hauptverfasser: Thygesen, Mikkel B, Munch, Henrik, Sauer, Jørgen, Cló, Emiliano, Jørgensen, Malene R, Hindsgaul, Ole, Jensen, Knud J
Format: Artikel
Sprache:eng
Schlagworte:
Aniline Compounds - chemistry
Carbohydrates - chemical synthesis
Carbohydrates - chemistry
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Catalysis
Chemistry
Exact sciences and technology
Glycoconjugates - chemical synthesis
Glycoconjugates - chemistry
Magnetic Resonance Spectroscopy
Models, Chemical
Molecular Sequence Data
Molecular Structure
Noncondensed benzenic compounds
Organic chemistry
Oximes - chemical synthesis
Oximes - chemistry
Polysaccharides - chemistry
Preparations and properties
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Zusammenfassung:Chemoselective formation of glycoconjugates from unprotected glycans is needed to further develop chemical biology involving glycans. Carbohydrate oxime formation is often slow, and organocatalysis by anilines would be highly promising. Here, we present that carbohydrate oxime formation can be catalyzed with up to 20-fold increases in overall reaction rate at 100 mM aniline. Application of this methodology provided access to complex glycoconjugates.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo902425v