The synthesis of biotinylated carbohydrates as probes for carbohydrate-recognizing proteins.
The intimate involvement of carbohydrate-protein interactions in a number of important biological processes has prompted several research efforts towards developing new methods of investigating these glycobiological interactions. Biotinylated oligosaccharides are emerging as a new and powerful tool in this area of research, primarily due to their high affinity towards streptavidin and their ease of immobilization on matrices. Here we describe a novel synthetic approach towards biotinylated saccharides which incorporate a UV absorbing group into the final compounds. The synthetic strategy described is applicable to a variety of saccharides, with examples of biotinylated mono-, di-, and trisaccharides being prepared with overall high efficiency.
Angus
D I
DI
Department of Medicinal Chemistry, Monash University, Parkville, Victoria, Australia.
Kiefel
M J
MJ
von Itzstein
M
M
D001710:Biotin / Q000737:chemistry; D050260:Carbohydrate Metabolism; D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D015335:Molecular Probes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D011506:Proteins / Q000378:metabolism*
D002241:Carbohydrates; D015335:Molecular Probes; D009844:Oligosaccharides; D011506:Proteins; D001710:Biotin