Convenient Synthesis of the Immunogenic Glycolipid BbGL1

14 November 2018, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

Acyl steryl glycosides
BbGL1
Lyme disease
microwave heating
selective acylation

Supplementary materials

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Jager et al revised
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