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 catalyzed with up to 20-fold increases in overall reaction rate at 100 mM aniline. Application of this methodology provided access to complex glycoconjugates.
Thygesen
Mikkel B
MB
IGM-Bioorganic Chemistry, Faculty of Life Sciences, University of Copenhagen, Thorvaldsensvej 40, DK-1871 Frederiksberg, Denmark.
Munch
Henrik
H
Sauer
Jørgen
J
Cló
Emiliano
E
Jørgensen
Malene R
MR
Hindsgaul
Ole
O
Jensen
Knud J
KJ
D000814:Aniline Compounds / Q000737:chemistry*; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010091:Oximes / Q000138:chemical synthesis* / Q000737:chemistry; D011134:Polysaccharides / Q000737:chemistry*
D000814:Aniline Compounds; D002241:Carbohydrates; D006001:Glycoconjugates; D010091:Oximes; D011134:Polysaccharides; C023650:aniline