Chemoenzymatic synthesis of a new class of macrocyclic oligosaccharides

Saddam Muthana, Hai Yu, Hongzhi Cao, Jiansong Cheng, Xi Chen

Research output: Contribution to journalArticle

56 Scopus citations

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 languageEnglish (US)
Pages (from-to)2928-2936
Number of pages9
JournalJournal of Organic Chemistry
Volume74
Issue number8
DOIs
StatePublished - Apr 17 2009

ASJC Scopus subject areas

  • Organic Chemistry

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