Synthesis of the starfish ganglioside LLG-3 tetrasaccharide.
The first synthesis of the ganglioside LLG-3 tetrasaccharide, which has attractive biological activities as well as a unique structure, is described. A C8-methoxy decorated sialic acid building block was initially prepared and a glycolic acid moiety was then introduced by sialylation. Amide condensation between the sialyl glycolic acid and an amino group at C5 on the sialyllactoside unit afforded the fully protected LLG-3 tetrasaccharide. Finally, the desired tetrasaccharide part of LLG-3 was obtained after careful global deprotection. [structure: see text].
Hanashima
Shinya
S
Material and Life Chemistry, Faculty of Engineering, Kanagawa University, Yokohama, Kanagawa, Japan.
Ishikawa
Daichi
D
Akai
Shoji
S
Sato
Ken-ichi
K
D000818:Animals; D002240:Carbohydrate Sequence; D005732:Gangliosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D019158:N-Acetylneuraminic Acid / Q000737:chemistry; D009438:Neuraminic Acids / Q000737:chemistry; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013215:Starfish / Q000737:chemistry*
D005732:Gangliosides; D009438:Neuraminic Acids; D009844:Oligosaccharides; C032592:N-glycolylneuraminic acid; D019158:N-Acetylneuraminic Acid