3-Mercaptopropanol as a traceless linker for chemical and enzymatic synthesis of oligosaccharides.
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].
Merbouh
Nabyl
N
The Burnham Institute for Medical Research, 10901 North Torrey Pines Road, La Jolla, California 92037, USA.
Wallner
Fredrik K
FK
Cociorva
Oana M
OM
Seeberger
Peter H
PH
D002240:Carbohydrate Sequence; D005944:Glucosamine / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D006031:Glycosylation; D007202:Indicators and Reagents; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D010777:Photochemistry; D020005:Propanols / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis*; D014466:Ultraviolet Rays
C518434:3-mercaptopropanol; D007202:Indicators and Reagents; D009844:Oligosaccharides; D020005:Propanols; D013438:Sulfhydryl Compounds; D005947:Glucose; D005944:Glucosamine