Convenient synthesis of the immunogenic glycolipid BbGL1

A simple and efficient method to synthesize the immunogenic glycolipid BbGL1 is introduced. Two simple steps were required to obtain the desired product in good yield. First, a highly efficient glycosylation of cholesterol using galactosyl trichloroacetimidate as a donor was performed to produce cho...

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Autores principales: Jäger, Sebastián N., Porta, Exequiel Oscar Jesús, Labadie, Guillermo Roberto
Formato: article artículo acceptedVersion
Lenguaje:Inglés
Publicado: Elsevier 2020
Materias:
Acyl steryl glycosides
BbGL1
Lyme disease
Microwave heating
Selective acylation
Acceso en línea:http://hdl.handle.net/2133/18280
http://hdl.handle.net/2133/18280
Aporte de:
Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR) de Universidad Nacional de Rosario
id I15-R121-2133-18280
record_format dspace
institution Universidad Nacional de Rosario
institution_str I-15
repository_str R-121
collection Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR)
language Inglés
topic Acyl steryl glycosides
BbGL1
Lyme disease
Microwave heating
Selective acylation
spellingShingle Acyl steryl glycosides
BbGL1
Lyme disease
Microwave heating
Selective acylation
Jäger, Sebastián N.
Porta, Exequiel Oscar Jesús
Labadie, Guillermo Roberto
Convenient synthesis of the immunogenic glycolipid BbGL1
topic_facet Acyl steryl glycosides
BbGL1
Lyme disease
Microwave heating
Selective acylation
description A simple and efficient method to synthesize the immunogenic glycolipid BbGL1 is introduced. Two simple steps were required to obtain the desired product in good yield. First, a highly efficient glycosylation of cholesterol using galactosyl trichloroacetimidate as a donor was performed to produce cholesteryl-β-d-galactoside. Finally, an efficient palmitoylation on the C6–OH of the galactose of the synthesized saponin using sym-collidine and acyl chloride under microwave heating that produced BbGL1 in good yield. The procedure is a convenient and cheaper alternative to the reported procedures allowing a rapid preparation of multiple analogs and conjugates.
format article
artículo
acceptedVersion
author Jäger, Sebastián N.
Porta, Exequiel Oscar Jesús
Labadie, Guillermo Roberto
author_facet Jäger, Sebastián N.
Porta, Exequiel Oscar Jesús
Labadie, Guillermo Roberto
author_sort Jäger, Sebastián N.
title Convenient synthesis of the immunogenic glycolipid BbGL1
title_short Convenient synthesis of the immunogenic glycolipid BbGL1
title_full Convenient synthesis of the immunogenic glycolipid BbGL1
title_fullStr Convenient synthesis of the immunogenic glycolipid BbGL1
title_full_unstemmed Convenient synthesis of the immunogenic glycolipid BbGL1
title_sort convenient synthesis of the immunogenic glycolipid bbgl1
publisher Elsevier
publishDate 2020
url http://hdl.handle.net/2133/18280
http://hdl.handle.net/2133/18280
work_keys_str_mv AT jagersebastiann convenientsynthesisoftheimmunogenicglycolipidbbgl1
AT portaexequieloscarjesus convenientsynthesisoftheimmunogenicglycolipidbbgl1
AT labadieguillermoroberto convenientsynthesisoftheimmunogenicglycolipidbbgl1
bdutipo_str Repositorios
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