Syntheses of two trimannose analogs each containing C-mannosyl or 5-thio-C-mannosyl residue: their affinities to concanavalin A.
C-Mannosyl residue-containing trimannose ManC alpha(1,6)[Man alpha(1,3)Man] (2) and 5-thio-C mannosyl residue-containing trimannose 5SManC alpha(1,6)[Man alpha(1,3)Man] (3) were synthesized via a glycosyl radical addition to enone derivative of mannose (6). Dissociation constants for the binding of these trisaccharides to concanavalin A (ConA) were determined by a fluorescence anisotropy inhibition assay: Kd = 198 and 31 microM, respectively. The unexpectedly large Kd value for the compound 2 compared with the compound 3 and the natural trimannose 1 demonstrates a characteristic of C-glycoside.
Tsuruta
O
O
Department of Life Science, Faculty of Bioscience and Biotechnology, Tokyo Institute of Technology, Yokohama, Japan.
Yuasa
H
H
Kurono
S
S
Hashimoto
H
H
D003208:Concanavalin A / Q000737:chemistry*; D007700:Kinetics; D008358:Mannose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D008956:Models, Chemical; D011485:Protein Binding
D003208:Concanavalin A; D008358:Mannose