Reactivity-based one-pot total synthesis of fucose GM1 oligosaccharide: A sialylated antigenic epitope of small-cell lung cancer

The total synthesis of the sialic acid-containing antigenic epitope fucose GM 1 (Fuc-GM 1 ) by 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...

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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, Duron, Sergio G, Wong, Chi-Huey
Format: Article
Language:English
Subjects:
Analysis
Carbohydrate Sequence
Carcinoma, Small Cell - immunology
Carcinoma, Small Cell - metabolism
Disaccharides
Epitopes
Fucose - chemistry
Lung cancer
Lung Neoplasms - immunology
Lung Neoplasms - metabolism
Molecular Sequence Data
N-Acetylneuraminic Acid - chemistry
Oligosaccharides - chemical synthesis
Oligosaccharides - chemistry
Physical Sciences
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Summary:The total synthesis of the sialic acid-containing antigenic epitope fucose GM 1 (Fuc-GM 1 ) by 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-GM 1 glycoside 2 was furnished in a facile manner, which was globally deprotected to give the Fuc-GM 1 glycoside 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. synthetic vaccine
ISSN:0027-8424
1091-6490
DOI:10.1073/pnas.0337590100