Organic Letters 2007-02-15

3-Mercaptopropanol as a traceless linker for chemical and enzymatic synthesis of oligosaccharides.

Nabyl Merbouh, Fredrik K Wallner, Oana M Cociorva, Peter H Seeberger

Index: Org. Lett. 9 , 651-653, (2007)

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Abstract

The reducing end of protected carbohydrates can be equipped with a series of aglycones via the photochemical installation of a 3-mercaptoethanol linker. This linker is stable during chemical and enzymatic glycosylation reactions but can be activated readily and efficiently to couple oligosaccharides with different nucleophiles. This approach provides straightforward access to a range of molecules that serve as probes for carbohydrate modifying enzymes. [reaction: see text].