A novel glycosphingolipid, β-d-Manp-(1→4)-[α-l-Fucp-(1→3)]-β-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 β-glucopyranoside residue yielding a β-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).
- Intermolecular nucleophile approach
- Parafontaria laminata armigera
ASJC Scopus subject areas
- Analytical Chemistry
- Organic Chemistry