Liquid crystalline glycosteroids and acyl steroid glycosides (ASG). Issue 12 (21st October 2017)

• Record Type: Journal Article
• Authors: Yang, Zonglong; Xu, Rui; Ali-Rachedi, Fahima; Chambert, Stéphane; Xavier, Nuno M.; Soulère, Laurent; Ahmar, Mohammed; Mackenzie, Grahame; Davis, Edward J.; Goodby, John W.; Cowling, Stephen J.; Queneau, Yves
• Is Part Of: Liquid crystals. Volume 44:Issue 12/13(2017)
• Page Start: 2089
• Page End: 2107
• Publication Date: 2017-10-21
• Subjects: Carbohydrate -- liquid crystal -- glycolipid -- bolaform -- bolaphile -- steroid -- ASG; Liquid crystals -- Periodicals; 548.905
• DOI: 10.1080/02678292.2017.1346211
• Languages: English
• ISSNs: 0267-8292

Abstract

ABSTRACT: 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. Graphical Abstract: