Gangliosides that contain the disialosyl residue α-Neu5Ac-(2→8)-α-Neu5Ac-(2→3)- can lactonize in the presence of traces of acid and this reaction has been studied in detail on GD1b {β-Gal-(1→3)-β-GalNAc-(1→4)-[α-Neu5Ac-(2→8)-α-Neu5Ac-(2→3)]-β-Gal-(1→4)-β-Glc-(1→1)-Cer}. Lactonization occurs rapidly at a proton-ganglioside molar ratio of ≫1. At equilibrium, the ratio of GD1b to its lactone is 3:7. The data suggest the possibility that a proton-driven lactonization of gangliosides may occur in vivo.
LACTONIZATION OF GD1B GANGLIOSIDE UNDER ACIDIC CONDITIONS / R. BASSI, L. RIBONI, S. SONNINO, G. TETTAMANTI. - In: CARBOHYDRATE RESEARCH. - ISSN 0008-6215. - 193:C(1989), pp. 141-146. [10.1016/0008-6215(89)85113-4]
LACTONIZATION OF GD1B GANGLIOSIDE UNDER ACIDIC CONDITIONS
R. BassiPrimo
;L. RiboniSecondo
;S. SonninoPenultimo
;G. TettamantiUltimo
1989
Abstract
Gangliosides that contain the disialosyl residue α-Neu5Ac-(2→8)-α-Neu5Ac-(2→3)- can lactonize in the presence of traces of acid and this reaction has been studied in detail on GD1b {β-Gal-(1→3)-β-GalNAc-(1→4)-[α-Neu5Ac-(2→8)-α-Neu5Ac-(2→3)]-β-Gal-(1→4)-β-Glc-(1→1)-Cer}. Lactonization occurs rapidly at a proton-ganglioside molar ratio of ≫1. At equilibrium, the ratio of GD1b to its lactone is 3:7. The data suggest the possibility that a proton-driven lactonization of gangliosides may occur in vivo.
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