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Org Lett ; 22(19): 7491-7495, 2020 10 02.
Article in English | MEDLINE | ID: mdl-32965122

ABSTRACT

A total synthesis of echinodermatous ganglioside LLG-3 with neuritogenic activity was accomplished by a convergent strategy. The synthesis of 2-hydroxyethyl 8-O-Me-α-sialoside 2 was started from the phenyl 7,8-di-O-Pico-thiosialoside 5, which can be chemoselectively removed the picoloyl group, and then the methyl group in 8-O-MeNeu5Ac moiety was chemoselectively prepared using TMSCHN2/FeCl3. For preparation of the terminal disialic unit, oxidative amidation was initially utilized by our group to efficiently construct the α(2,11) linkage of 8-O-Me-Neu5Acα(2,11)Neu5Gc. Herein, we also demonstrate that the synthesized ganglioside LLG-3 exhibited the neuritogenic activity toward the primary cortical neurons and that biological activity is superior to that of ganglioside DSG-A.


Subject(s)
Gangliosides/chemical synthesis , Gangliosides/pharmacology , Neurons/chemistry , Animals , Glycosylation , Molecular Structure , Neuronal Outgrowth/physiology , PC12 Cells , Rats
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