Chemoenzymatic synthesis of a new class of macrocyclic oligosaccharides.
A novel and highly efficient chemoenzymatic method has been developed for the preparation of structurally defined macrocyclic oligosaccharides of varied sizes. This method involves chemical or chemoenzymatic synthesis of oligosaccharides containing a galactose at the nonreducing end and a propargyl group at the reducing end as sialyltransferase acceptors. Introducing an azido-containing sialic acid to the nonreducing end of the galactosides through a sialyltransferase-catalyzed enzymatic reaction followed by copper(I)-catalyzed Huisgen's 1,3-dipolar cycloaddition of alkyne and azide provides size-defined macrocyclic carbohydrates. The produced negatively charged macrocycles have high solubility in water and interact with hydrophobic small molecules in a size-dependent manner.
Muthana
Saddam
S
Department of Chemistry, One Shields Avenue, University of California, Davis, California 95616, USA.
Yu
Hai
H
Cao
Hongzhi
H
Cheng
Jiansong
J
Chen
Xi
X
D001386:Azides / Q000737:chemistry*; D002241:Carbohydrates; D002384:Catalysis; D003432:Cross-Linking Reagents / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D019075:Electrophoresis, Capillary; D004800:Enzymes, Immobilized / Q000138:chemical synthesis* / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D012799:Sialyltransferases / Q000737:chemistry* / Q000378:metabolism*; D012995:Solubility; D013050:Spectrometry, Fluorescence
D001386:Azides; D002241:Carbohydrates; D003432:Cross-Linking Reagents; D004800:Enzymes, Immobilized; D047028:Macrocyclic Compounds; D009844:Oligosaccharides; D012799:Sialyltransferases