90980-78-2Relevant articles and documents
Efficient diversification of GM3 gangliosides: Via late-stage sialylation and dynamic glycan structural studies with 19F solid-state NMR
Ando, Hiromune,Hanashima, Shinya,Imamura, Akihiro,Ishida, Hideharu,Komura, Naoko,Murata, Michio,Sasaki, Katsuaki,Shirasaki, Junya,Takahashi, Maina,Tanaka, Hide-Nori
, p. 2902 - 2913 (2020/04/28)
Sialic acid-containing glycoconjugates are involved in important biological processes such as immune response, cancer metastasis, and viral infection. However, their chemical syntheses have been challenging, mainly due to the difficulties in the α-sialylation of oligosaccharides. Very recently, we established a completely stereoselective sialidation method using a macrobicyclic sialyl donor. Herein, we describe a rational and efficient synthesis of sialoglycolipids via direct sialylation of a glycolipid at a late-stage, based on our novel sialidation method. The synthetic method enabled the development of GM3 ganglioside analogs with various C5-modifications of the sialosyl moiety. Furthermore, the synthesized analog was subjected to solid-state 19F NMR analysis on the model membranes and it revealed the influence of cholesterol on glycan dynamics.
Solid-phase synthesis of oligosaccharides and on-resin quantitative monitoring using gated decoupling 13C NMR
Kanemitsu, Takuya,Wong, Chi-Huey,Kanie, Osamu
, p. 3591 - 3599 (2007/10/03)
A general strategy for solid-phase oligosaccharide synthesis capable of nondestructive quantitative monitoring has been developed. The synthesis was carried out on TentaGel using thioglycosides as glycosylating agents and dimethylthiomethylsulfonium triflate as the activator. An acylsulfonamide linker was introduced to cleave the oligosaccharide from the resin. The solid-phase reactions were monitored quantitatively by using the inverse gated decoupling technique of 13C NMR, where two 13C-enriched markers were used to monitor the reactions: one was 13C-enriched glycine incorporated as a part of the linker and as an internal standard, and the other was a 13C-enriched acetyl group used as a protecting group of the glycosylation reagent. A representative synthesis of sialyl Lewis X branched tetrasaccharide was demonstrated.