104556-69-6Relevant academic research and scientific papers
Use of a recycle-type SEC method as a powerful tool for purification of thiosialoside derivatives
Sakamoto, Jun-Ichi,Takita, Chiharu,Koyama, Tetsuo,Hatano, Ken,Terunuma, Daiyo,Matsuoka, Koji
, p. 2735 - 2739 (2008)
An efficient separation between fully acetylated thiosialoside methyl esters and fully acetylated Neu5Ac2en methyl esters was accomplished by means of a size-exclusion chromatography (SEC) method. Purity determinations and structural elucidation of the isolated compounds were performed by a combination of elemental analyses and spectroscopic analyses, including IR, 1H, and 13C NMR, and mass spectroscopic analyses.
One pot synthesis of thio -glycosides via aziridine opening reactions
Hribernik, Nives,Tamburrini, Alice,Falletta, Ermelinda,Bernardi, Anna
supporting information, p. 233 - 247 (2021/01/14)
A one-pot aziridine opening reaction by glycosyl thiols generated in situ from the corresponding anomeric thio-acetates affords thio-glycosides with a pseudo-disaccharide structure and an N-linked tether. The scope of the one-pot aziridine opening reaction was explored on a series of mono- and disaccharides, creating a class of pseudo-glycosidic compounds with potential for further functionalization. Unexpected anomerization of glycosyl thiols was observed under the reaction conditions and the influence of temperature, base and solvent on the isomerization was investigated. Single isomers were obtained in good to acceptable yields for mannose, rhamnose and sialic acid derivatives. The class of thio-glycomimetics synthesized can potentially be recognized by various lectins, while presenting hydrolytic and enzymatic stability. The nitrogen functionality incorporated in the glycomimetics can be exploited for further functionalization, including tethering to linkers, scaffolds or peptide residues.
Systematic syntheses of influenza neuraminidase inhibitors: A series of carbosilane dendrimers uniformly functionalized with thioglycoside-type sialic acid moieties
Sakamoto, Jun-Ichi,Koyama, Tetsuo,Miyamoto, Daisei,Yingsakmongkon, Sangchai,Hidari, Kazuya I.P.J.,Jampangern, Wipawee,Suzuki, Takashi,Suzuki, Yasuo,Esumi, Yasuaki,Nakamura, Takemichi,Hatano, Ken,Terunuma, Daiyo,Matsuoka, Koji
scheme or table, p. 5451 - 5464 (2009/12/09)
In order to develop novel influenza sialidase inhibitors, we constructed a library of glycoclusters composed of twelve types of sialylated dendrimers with thioglycosidic linkage that are resistant to hydrolysis by the sialidases. These sialodendrimers were synthesized by condensation reaction between a thiosialoside modified on the aglycon terminal end by a thioacetyl group and twelve types of carbosilane dendrimers having brominated terminal ends under deacetylation conditions, and temporal re-protection was performed for purification. Removal of all protection of the glycodendrimers was accomplished by transesterification and subsequent saponification to provide corresponding water-soluble glycodendrimers in good yields. For investigation of the structure-activity relationship, dendrimer scaffolds having differences in number of the sugar moieties, such as 3-, 4-, 6- and 12-functionalized dendrimers, and in linkage patterns, such as normal aliphatic linkage, ether- and amide-linkages. Biological evaluations of these glycodendrimers showed that all of the ether- and amide-elongated compounds had inhibitory potencies for the influenza sialidases in the mM range, while compounds having normal aliphatic linkage did not have any activities except for a 12-functionalized compound.
