3 years ago

Liquid crystalline glycosteroids and acyl steroid glycosides (ASG)

Liquid crystalline glycosteroids and acyl steroid glycosides (ASG)
Edward J. Davis, Laurent Soulère, Yves Queneau, Stephen J. Cowling, Grahame Mackenzie, Mohammed Ahmar, Stéphane Chambert, John W. Goodby, Rui Xu, Zonglong Yang, Fahima Ali-Rachedi, Nuno M. Xavier

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 Borrelia burgdorferi and Helicobacter pylori, 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-O-acyl-β-gluco- and -galacto-pyranosides.

Publisher URL: http://www.tandfonline.com/doi/full/10.1080/02678292.2017.1346211

DOI: 10.1080/02678292.2017.1346211

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