Synthesis of globo- and isoglobotriosides bearing a cinnamoylphenyl tag as novel electrophilic thiol-specific carbohydrate reagents.
The galactosyl donor, 4,6-di-O-acetyl-2,3-di-O-benzyl-D-galactopyranosyl trichloroacetimidate, was efficiently coupled with regioselectively benzylated lactoside acceptors under standard conditions to stereoselectively afford the corresponding globotrioside and isoglobotrioside derivatives in very good yields. These glycosides were smoothly functionalized with a 6-(p-cinnamoylphenoxy)-hexyl tether tag as novel electrophilic thiol-specific carbohydrate reagents. Immobilization of the globotrioside conjugate to Thiopropyl Sepharose 6B for purification of B-subunit of Shiga toxin (StxB) and coupling of a model cysteine-containing protein (StxB-Z(n)-Cys) to the isoglobotrioside conjugate were both performed with high efficiency.
Aly
Mohamed R E
MR
Laboratoire de Chimie UMR 176 CNRS-Institut Curie, 26 rue d'Ulm, F-75248 Paris, France.
Rochaix
Pascal
P
Amessou
Mohamed
M
Johannes
Ludger
L
Florent
Jean-Claude
JC
D002240:Carbohydrate Sequence; D002599:Chalcone / Q000737:chemistry; D002934:Cinnamates / Q000737:chemistry; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D010636:Phenols / Q000737:chemistry; D012685:Sepharose / Q000031:analogs & derivatives / Q000737:chemistry; D022621:Shiga Toxin / Q000737:chemistry / Q000302:isolation & purification; D013439:Sulfhydryl Reagents / Q000138:chemical synthesis* / Q000737:chemistry; D014306:Trioses / Q000138:chemical synthesis* / Q000737:chemistry
D002934:Cinnamates; D009844:Oligosaccharides; D010636:Phenols; D013439:Sulfhydryl Reagents; D014306:Trioses; D002599:Chalcone; C047264:sepharose CL 6B; D022621:Shiga Toxin; D012685:Sepharose