Synthesis and binding to plant lectins of sulfur-containing analogues of betaGal1,3 alphaGalNAc (T-antigen).
Analogues of the tumor-associated T-antigen (betaGal1,3 alphaGalNAc) containing 4,6-epidithio and 4,6-thietan modifications were synthesized from the alpha-allyl glycoside of betaGal alpha1,3GlcNAc via suitable thiocyanate derivatives. Binding to three leguminous lectins as model systems was investigated in an enzyme-linked lectin assay (ELLA) and IC50 values comparable to the corresponding natural disaccharides T-antigen, lactose and N-acetyllactosamine were found.
Streicher
H
H
Faculty of Chemistry, University of Konstanz, Germany. hansjoerg.streicher@uni-konstanz.de
Schmid
W
W
Wenzl
I
I
Fiedler
C
C
Kählig
H
H
Unger
F M
FM
D000957:Antigens, Viral, Tumor / Q000737:chemistry / Q000378:metabolism*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D037102:Lectins / Q000138:chemical synthesis* / Q000378:metabolism; D037121:Plant Lectins; D010944:Plants / Q000737:chemistry*; D013455:Sulfur / Q000032:analysis*
D000957:Antigens, Viral, Tumor; D037102:Lectins; D037121:Plant Lectins; D013455:Sulfur