Synthesis of a novel glycosphingolipid from the millipede, Parafontaria laminata armigera, and the assembly of its carbohydrate moiety into multivalent structures.
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).
Hada
Noriyasu
N
Kyoritsu University of Pharmacy, 1-5-30 Shibakoen, Tokyo 105-8512, Japan.
Sonoda
Yoshiko
Y
Takeda
Tadahiro
T
D000818:Animals; D001181:Arthropods / Q000737:chemistry; D002240:Carbohydrate Sequence; D006028:Glycosphingolipids / Q000138:chemical synthesis*; D008969:Molecular Sequence Data
D006028:Glycosphingolipids; C090437:mannosyl-1-4-(fucosyl-1-3)glucosyl-1-ceramide