Liquid crystalline glycosteroids and acyl steroid glycosides (ASG)

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

KEYWORDS:

• Carbohydrate
• liquid crystal
• glycolipid
• bolaform
• bolaphile
• steroid
• ASG

Acknowledgements

This paper is dedicated to Prof. John W. Goodby, FRS, on the occasion of his 65th birthday, and in recognition of his considerable research and teaching achievements in liquid-crystal science and his continuing efforts for making it understood by the general public, useful to other scientific disciplines and applicable in various industrial sectors. This article represents an expression of gratitude for the intense, exciting and friendly collaboration between Prof. John Goodby and the Lyon team (nearly 20 years) and also for the York-Hull colleagues. We look forward to its continuation.

Disclosure statement

No potential conflict of interest was reported by the authors.

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Additional information

Funding

Financial support from CNRS and MESRI is gratefully acknowledged, as well as China Scholarship Council for a Ph.D. grant to Z.Y.