First total synthesis of alpha-(2-->3)/alpha-(2-->6)-disialyl lactotetraosyl ceramide and disialyl Lewis A ganglioside as cancer-associated carbohydrate antigens.
The first total synthesis of alpha-(2-->3)/alpha-(2-->6)-disialyl lactotetraosyl (DSLc4) ceramide and alpha-(2-->3)/alpha-(2-->6)-disialyl Lewis A (DSLe(a)) ganglioside as cancer-associated antigens is described. The suitably protected lactotriose (Lc3) derivatives were successively glycosylated with sialic acid, sialyl-alpha-(2-->3)-D-galactose and/or L-fucose donors in a regio- and stereo-selective manner, to give the protected type I hexa- and hepta-saccharides, respectively, which were then converted to the target gangliosides by the introduction of ceramide and subsequent complete deprotection.
Ando
Takayuki
T
Department of Applied Bioorganic Chemistry, Gifu University, 501-1193, Gifu, Japan.
Ishida
Hideharu
H
Kiso
Makoto
M
D015295:Antigens, Tumor-Associated, Carbohydrate / Q000737:chemistry*; D018395:CA-19-9 Antigen; D002240:Carbohydrate Sequence; D005647:Fucosyltransferases / Q000378:metabolism; D005732:Gangliosides / Q000737:chemistry; D006028:Glycosphingolipids / Q000737:chemistry; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry; D013329:Structure-Activity Relationship
D015295:Antigens, Tumor-Associated, Carbohydrate; D018395:CA-19-9 Antigen; D005732:Gangliosides; D006028:Glycosphingolipids; D009844:Oligosaccharides; C458510:lactotetraosylceramide; C064564:sialyl Le(a) ganglioside; D005647:Fucosyltransferases