Concepedia

Synthesis of the Disialic Acid-Embedded Glycan Part of Ganglioside HPG-1

Hiroyo Shimizu, Yuki Iwayama, Akihiro Imamura, Hiromune Ando, Hideharu Ishida, Makoto Kiso

Bioscience Biotechnology and Biochemistry · 2011 · 15 citations · 16 references

DOIFull text

Open access

Concepts

Abstract

Synthesis of tetrasaccharide portion of ganglioside HPG-1 is described. The tetrasaccharide sequence, Fuc-α(1,8)-Neu5Gc-α(2,4)-Neu5Ac-α(2,6)-Glc, was successfully assembled by a linear strategy, in which the 1,5-lactamized sialyl galactose acceptor and the 8-O-Lev-N-Troc-sialic acid donor were exploited as key units.

References

16

Iodonium ion promoted reactions at the anomeric centre. II An efficient thioglycoside mediated approach toward the formation of 1,2-trans linked glycosides and glycosidic esters

G.H. Veeneman, Steven H. van Leeuwen, Jacques H. van Boom · Tetrahedron Letters · 1990 · 861 citations

, , +7

Reductive Ring Openings of Carbohydrate Benzylidene Acetals Using Borane-Trimethylamine and Aluminium Chloride. Regioselectivity and Solvent Dependance

M. EK, Per J. Garegg, Hans Hultberg et al. · Journal of Carbohydrate Chemistry · 1983 · 179 citations

, , +12

Communication: Synthetic Studies on Sialoglycoconjugates 25: Reactivity of Glycosyl Promoters in α-Glycosylation of N-Acetyl-Neuraminic Acid with the Primary and Secondary Hydroxyl Groups in the Suitably Protected Galactose and Lactose Derivatives

Akira Hasegawa, Takao Nagahama, Hitoshi Ohki et al. · Journal of Carbohydrate Chemistry · 1991 · 161 citations

, , +16

Total synthesis of the tumor-associated Lex family of glycosphingolipids

K. C. Nicolaou, Thomas J. Caulfield, Hiromi Kataoka et al. · Journal of the American Chemical Society · 1990 · 150 citations

, , +16

Extending the possibility of an N-Troc-protected sialic acid donor toward variant sialo-glycoside synthesis

Hiromune Ando, Yusuke Koike, Hideharu Ishida et al. · Tetrahedron Letters · 2003 · 126 citations

, , +8