Efficient diversification of GM3 gangliosides via late-stage sialylation and dynamic glycan structural studies with 19F solid-state NMR

Autor:	Shinya Hanashima, Hidenori Tanaka, Maina Takahashi, Hiromune Ando, Junya Shirasaki, Michio Murata, Akihiro Imamura, Katsuaki Sasaki, Naoko Komura, Hideharu Ishida
Rok vydání:	2020
Předmět:	chemistry.chemical_classification Glycan biology Chemistry Glycoconjugate Organic Chemistry Late stage Fluorine-19 NMR Biochemistry carbohydrates (lipids) Glycolipid Membrane Solid-state nuclear magnetic resonance biology.protein Moiety Physical and Theoretical Chemistry
Zdroj:	Organic & Biomolecular Chemistry. 18:2902-2913
ISSN:	1477-0539 1477-0520
DOI:	10.1039/d0ob00437e
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::ce39e875d5dfba543b8040a5c1c39fbb https://doi.org/10.1039/d0ob00437e Zobrazit plný text záznamu