Facile Synthesis of a Library of Lyme Disease Glycolipid Antigens

A library of one of the two Lyme disease antigens, BbGL1, has been synthesized in four steps from d-galactose using BF3-promoted glycosylation of the peracetate to introduce the cholesteryl β-glycoside and TBTU-promoted esterification to add a range of fatty acids regioselectively at O-6 of d-galact...

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Bibliographic Details
Published in:Organic letters 2012-08, Vol.14 (15), p.3909-3911
Main Authors: Twibanire, Jean-d’Amour K, Omran, Raha Parvizi, Grindley, T. Bruce
Format: Article
Language:English
Subjects:
Borrelia burgdorferi - chemistry
Galactose - chemistry
Glycolipids - chemical synthesis
Glycolipids - chemistry
Glycolipids - immunology
Humans
Lyme Disease - immunology
Molecular Structure
Saponins - chemical synthesis
Saponins - chemistry
Saponins - immunology
Stereoisomerism
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Summary:A library of one of the two Lyme disease antigens, BbGL1, has been synthesized in four steps from d-galactose using BF3-promoted glycosylation of the peracetate to introduce the cholesteryl β-glycoside and TBTU-promoted esterification to add a range of fatty acids regioselectively at O-6 of d-galactose in good yield.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol301697c