Convenient synthesis of the immunogenic glycolipid BbGL1

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.

Garbage in, garbage out: how reliable training data improved a virtual screening approach against SARS-CoV-2 MPro

“…The compounds were provided by a large consortium of chemistry groups that co-authored this study. For the majority of the compounds, details about their synthesis and characterization can be found in the following references ( Hayashi et al, 1980 ; Mallet et al, 1993 ; Zagotto et al, 1993 ; Agnihotri et al, 2005 ; Agnihotri and Misra, 2005 ; Crich and Vinod, 2005 ; Bohn et al, 2006 ; Bohn et al, 2007 ; Porcal et al, 2007 ; Chilin et al, 2008 ; Ducray et al, 2008 ; Castro et al, 2009 ; Mong et al, 2009 ; Zhang et al, 2009 ; Sato et al, 2010 ; Spampinato et al, 2010 ; Basu et al, 2011 ; Colombo et al, 2011 ; Tatina et al, 2012 ; Benítez et al, 2016 ; Ribaudo et al, 2016 ; Jäger et al, 2019 ; Posada and Serra, 2019 ; Posada et al, 2020 ; Zhu and Xie, 2020 ; Irabuena et al, 2022 ; Istifli et al, 2022 ; Posada et al, 2022 ; Colobbio et al, 2023 ) or will be published elsewhere.…”

Steryl Glycosides in Fungal Pathogenesis: An Understudied Immunomodulatory Adjuvant

“…In more detail, two different strains of Pichia pastoris and one strain of Sordaria macrospora were shown to all produce β-D-glucopyranoside, but the two different strains of P. pastoris were shown to produce differing levels of SGs and also be dependent on the type of stressor. Furthermore, little was known about the function of SGs in animals and bacteria as most of the research has been focused in plants and fungi, although knowledge regarding SG metabolism in mammals and bacteria is beginning to open up [44,45,59,63]. Overall, SGs are not one compound but an umbrella term used to describe the addition of a variable sugar moiety to a sterol species, so the diverse effects reported in the literature is justified.…”

“…about the function of SGs in animals and bacteria as most of the research has been focused in plants and fungi, although knowledge regarding SG metabolism in mammals and bacteria is beginning to open up [44,45,59,63]. Overall, SGs are not one compound but an umbrella term used to describe the addition of a variable sugar moiety to a sterol species, so the diverse effects reported in the literature is justified.…”

“…Studies such as this and earlier ones found certain lipids to have an immunogenic response. Indeed, the roles of certain glycosylated lipids decorated with various acyl groups was an important topic to the point that several reports were published on the synthesis [63] and crystal structures [84] of certain lipids and associated bacterial enzymes for increased study and characterization.…”