Liquid crystalline glycosteroids and acyl steroid glycosides (ASG)
Zonglong Yang
Rui Xu
Fahima Ali-Rachedi
Stéphane Chambert
Nuno M. Xavier
Laurent Soulère
Mohammed Ahmar
Grahame Mackenzie
Edward J. Davis
John W. Goodby
Stephen J. Cowling
Yves Queneau
10.6084/m9.figshare.5182594
https://tandf.figshare.com/articles/journal_contribution/Liquid_crystalline_glycosteroids_and_acyl_steroid_glycosides_ASG_/5182594
<p>As part of our studies on glycolipidic liquid crystals, we have investigated some molecules comprising a steroid moiety. These systems can exhibit several types of structures depending on their polarity pattern based on the number of polar and non-polar moieties and their resulting molecular shape. Therefore, to aid describing such systems, we have proposed a specific classification based on this polarity pattern. Many compounds in this family are natural products, which possess important biological properties. Some of the compounds have bolaphilic structures, with both a steroid and a fatty alkyl chain attached to the carbohydrate moiety, such as either the β-galactoside BbGL-1 or the α-glucoside α-CAG that are found in the membranes of the pathogens <i>Borrelia burgdorferi</i> and <i>Helicobacter pylori</i>, respectively. In this account, after a brief introduction on liquid crystalline glycolipids, we focus on carbohydrate–steroid hybrids, summarising our previous work on glycosteroids prepared by the CMGL-synthon strategy, and reporting our preliminary results on the thermotropic behaviour of acyl steroid glycosides (ASG), namely cholesteryl 6-<i>O</i>-acyl-β-gluco- and -galacto-pyranosides.</p>
2017-07-07 07:29:30
Carbohydrate
liquid crystal
glycolipid
bolaform
bolaphile
steroid
ASG