Total syntheses of disulphated glycosphingolipid SB1a and the related monosulphated SM1a

Total syntheses of disulphated glycosphingolipid SB1a and the related monosulphated SM1a

Total syntheses of two natural sulphoglycolipids, disulphated glycosphingolipid SB1a and the structurally related monosulphated SM1a, are described. They have common glycan sequences and ceramide moieties and are associated with human epithelial carcinomas. The syntheses featured efficient glycan as...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic & biomolecular chemistry 2015-01, Vol.13 (45), p.11105-11117
Hauptverfasser: Hirose, Haruka, Tamai, Hideki, Gao, Chao, Imamura, Akihiro, Ando, Hiromune, Ishida, Hideharu, Feizi, Ten, Kiso, Makoto
Format: Artikel
Sprache:eng
Schlagworte:
Carcinoma - chemistry
Ceramides - chemical synthesis
Ceramides - chemistry
Glycosphingolipids - chemical synthesis
Glycosphingolipids - chemistry
Humans
Microarray Analysis
Polysaccharides - chemical synthesis
Polysaccharides - chemistry
Sulfur Compounds - chemical synthesis
Sulfur Compounds - chemistry
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Total syntheses of two natural sulphoglycolipids, disulphated glycosphingolipid SB1a and the structurally related monosulphated SM1a, are described. They have common glycan sequences and ceramide moieties and are associated with human epithelial carcinomas. The syntheses featured efficient glycan assembly and the glucosyl ceramide cassette as a versatile building block. The binding of the synthetic sulphoglycolipids by the carcinoma-specific monoclonal antibody AE3 was investigated using carbohydrate microarray technology.
ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob01744k