Abstract
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.
Original language | English (US) |
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Pages (from-to) | 2928-2936 |
Number of pages | 9 |
Journal | Journal of Organic Chemistry |
Volume | 74 |
Issue number | 8 |
DOIs | |
State | Published - Apr 17 2009 |
ASJC Scopus subject areas
- Organic Chemistry