Multivalent galacto-trehaloses: design, synthesis, and biological evaluation under the concept of carbohydrate modules.
Galacto-trehalose (GT) is a novel class of 1,1'-linked nonreducing disaccharide having an α-galactoside epitope. In this study, a pair of α,α- and α,β-GT isomers were prepared in one pot with our α-glycosylation method, converted into vinyl monomers and then subjected to radical copolymerization with a second sugar (4-acrylamidophemyl β-Glc or β-GlcNAc) in the presence of acrylamide. The derived glycopolymers were assayed with α-galactoside-specific proteins (BSI-B(4) lectin and Shiga toxin-1) to show the results that both α,α- and α,β-isomers are recognized by these carbohydrate-binding proteins more strongly in forms of the GT polymers. Moreover, the glycopolymer carrying both α,α-GT and β-GlcNAc along the polymer chain showed an integrated detoxifying activity to the E. coli toxin as the result of a "module effect" of the second sugar.
Miyachi
Akira
A
Graduate School of Engineering, Nagoya University, Nagoya 464-8603, Japan.
Dohi
Hirofumi
H
Neri
Paola
P
Mori
Hiroshi
H
Uzawa
Hirotaka
H
Seto
Yasuo
Y
Nishida
Yoshihiro
Y
D001427:Bacterial Toxins / Q000037:antagonists & inhibitors*; D002241:Carbohydrates / Q000138:chemical synthesis / Q000494:pharmacology; D004926:Escherichia coli; D037102:Lectins / Q000378:metabolism; D022622:Shiga Toxin 1 / Q000378:metabolism; D014199:Trehalose / Q000138:chemical synthesis* / Q000494:pharmacology*
D001427:Bacterial Toxins; D002241:Carbohydrates; D037102:Lectins; D022622:Shiga Toxin 1; D014199:Trehalose