Synthesis of a novel glycosphingolipid from the millipede, Parafontaria laminata armigera, and the assembly of its carbohydrate moiety into multivalent structures

Carbohydr Res. 2006 Jul 24;341(10):1341-52. doi: 10.1016/j.carres.2006.04.019. Epub 2006 May 15.

Abstract

A novel glycosphingolipid, beta-D-Manp-(1-->4)-[alpha-L-Fucp-(1-->3)]-beta-D-Glcp-(1-->1)-Cer, found in the millipede, Parafontaria laminata armigera, and multivalent derivatives of its carbohydrate moiety were synthesized. As the key step, the target glycolipid (1) was obtained through an inversion reaction at the 2-position of a beta-glucopyranoside residue yielding a beta-mannopyranoside. In addition, the synthesis of fluorescently labeled trimer and tetramer glycoconjugates (2, 3) was achieved by iterative amide bond formation using a monomer unit (24).

MeSH terms

  • Animals
  • Arthropods / chemistry
  • Carbohydrate Sequence
  • Glycosphingolipids / chemical synthesis*
  • Molecular Sequence Data

Substances

  • Glycosphingolipids
  • mannosyl-1-4-(fucosyl-1-3)glucosyl-1-ceramide