Reactivity-Based One-Pot Total Synthesis of Fucose GM1Oligosaccharide: A Sialylated Antigenic Epitope of Small-Cell Lung Cancer

The total synthesis of the sialic acid-containing antigenic epitope fucose GM1(Fuc-GM1by an improved reactivity-based one-pot synthetic strategy is reported. Based on a thioglycoside reactivity database, three saccharide building blocks, 3, 4, and 5, were designed and prepared to incorporate a desce...

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Bibliographic Details
Published in:Proceedings of the National Academy of Sciences - PNAS 2003-02, Vol.100 (3), p.797-802
Main Authors: Mong, Tony Kwok-Kong, Lee, Hing-Ken, Durón, Sergio G., Wong, Chi-Huey
Format: Article
Language:English
Subjects:
Brines
Chromatography
Disaccharides
Glycosides
Hydroxyls
Physical Sciences
Reactivity
Reagents
Residential buildings
Room temperature
Trisaccharides
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Summary:The total synthesis of the sialic acid-containing antigenic epitope fucose GM1(Fuc-GM1by an improved reactivity-based one-pot synthetic strategy is reported. Based on a thioglycoside reactivity database, three saccharide building blocks, 3, 4, and 5, were designed and prepared to incorporate a descending order of reactivity toward thiophilic activation. Using the reactivity-based one-pot synthetic method, the fully protected Fuc-GM1glycoside 2 was furnished in a facile manner, which was globally deprotected to give the Fuc-GM1glycoside 1. In addition, using the promoter system 1-(benzensulfinyl)piperidine/trifluoromethanesulfonic anhydride, the product yield was improved and the reaction time was reduced in comparison with the N-iodosuccinimide/trifluoromethanesulfonic acid- and dimethyl (thiomethyl) sulfonium trifluoromethanesulfonate-promoted systems.
ISSN:0027-8424