First total synthesis of alpha-(2-->3)/alpha-(2-->6)-disialyl lactotetraosyl ceramide and disialyl Lewis A ganglioside as cancer-associated carbohydrate antigens

Carbohydr Res. 2003 Mar 14;338(6):503-14. doi: 10.1016/s0008-6215(02)00465-2.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antigens, Tumor-Associated, Carbohydrate / chemistry*
  • CA-19-9 Antigen
  • Carbohydrate Sequence
  • Fucosyltransferases / metabolism
  • Gangliosides / chemistry
  • Glycosphingolipids / chemistry
  • Molecular Sequence Data
  • Oligosaccharides / chemical synthesis
  • Oligosaccharides / chemistry
  • Structure-Activity Relationship

Substances

  • Antigens, Tumor-Associated, Carbohydrate
  • CA-19-9 Antigen
  • Gangliosides
  • Glycosphingolipids
  • Oligosaccharides
  • lactotetraosylceramide
  • sialyl Le(a) ganglioside
  • Fucosyltransferases