Efficiently synthesizing lacto-ganglio-series gangliosides by using a glucosyl ceramide cassette approach: the total synthesis of ganglioside X2.
Chem Asian J
; 7(5): 1041-51, 2012 May.
Article
em En
| MEDLINE
| ID: mdl-22334413
ABSTRACT
The first total synthesis of the hybrid ganglioside X2, which consisted of a highly branched octasaccharide and ceramide moieties, was accomplished by using a glucosyl ceramide cassette approach. With a disaccharyl donor, the heptasaccharide could not be constructed by glycosylation of the C4 hydroxy group of galactose at the reducing end of the pentasaccharide. In contrast, through an alternative approach with two branched glycan units, a GM2-core trisaccharide, and a lacto-ganglio tetrasaccharide, the heptasaccharyl donor could be prepared and subsequently joined with a glucosyl ceramide cassette to afford the protected ganglioside, X2. Finally, global deprotection completed the synthesis, thus affording the pure ganglioside X2.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Ceramidas
/
Gangliosídeos
/
Glucosilceramidas
Limite:
Animals
/
Humans
Idioma:
En
Revista:
Chem Asian J
Ano de publicação:
2012
Tipo de documento:
Article
País de afiliação:
Japão