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Convenient Synthesis of the Immunogenic Glycolipid BbGL1

preprint
submitted on 13.11.2018, 20:20 and posted on 14.11.2018, 15:04 by Sebastián N. Jäger, Exequiel O. J. Porta, Guillermo Labadie
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--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.

Funding

CONICET (Consejo Nacional de Investigaciones Científicas y Técnicas, PIP 2009-11/0796 and PIP 2012-14/0448)

Agencia Nacional de Promoción Científica y Tecnológica (PICT-2011-0589)

History

Email Address of Submitting Author

labadie@iquir-conicet.gov.ar

Institution

IQUIR-CONICET

Country

Argentina

ORCID For Submitting Author

0000-0003-2467-1573

Declaration of Conflict of Interest

NO

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