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1. (Article ID: 1600)
 
Adamo R, Saksena R, Kovác P
Synthesis of the b anomer of the spacer-equipped tetrasaccharide side chain of the major glycoprotein of the Bacillus anthracis exosporium
Carbohydrate Research 340(17) (2005) 2579-2582
 

The beta glycoside of the tetrasaccharide sequence β-Ant-(1→3)-α-L-Rhap-(1→3)-α-L-Rhap-(1→2)-l-Rhap, whose aglycon allows conjugation to proteins, was synthesized for the first time. A stepwise synthetic approach was applied with thioglycosides as glycosyl donors, and the beta anomer of the compound was obtained equipped with a spacer group whose further transformation allows conjugation to suitable carriers. To synthesize the β-anthrosyl linkage with high stereoselectivity, a linker-equipped rhamnotriose derivative was glycosylated with ethyl 4-azido-3-O-benzyl-2-O-bromoacetyl-4,6-dideoxy-1-thio-β-D-glucopyranosi de. Further functionalization of the tetrasaccharide thus obtained, followed by deprotection, gave the target substance.

oligosaccharide, Anthrax, Anthrose, Exosporium glycoprotein, Thioglycoside

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