Liquid crystalline glycosteroids and acyl steroid glycosides (ASG)

TY - JOUR

T1 - Liquid crystalline glycosteroids and acyl steroid glycosides (ASG)

AU - Yang, Zonglong

AU - Xu, Rui

AU - Ali-Rachedi, Fahima

AU - Chambert, Stéphane

AU - Xavier, Nuno M.

AU - Soulère, Laurent

AU - Ahmar, Mohammed

AU - Mackenzie, Grahame

AU - Davis, Edward J.

AU - Goodby, John W.

AU - Cowling, Stephen J.

AU - Queneau, Yves

PY - 2017/10/30

Y1 - 2017/10/30

N2 - 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.

AB - 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.

KW - ASG

KW - bolaform

KW - bolaphile

KW - Carbohydrate

KW - glycolipid

KW - liquid crystal

KW - steroid

UR - http://www.scopus.com/inward/record.url?scp=85021872169&partnerID=8YFLogxK

U2 - 10.1080/02678292.2017.1346211

DO - 10.1080/02678292.2017.1346211

M3 - Article

AN - SCOPUS:85021872169

SN - 0267-8292

VL - 44

SP - 2089

EP - 2107

JO - LIQUID CRYSTALS

JF - LIQUID CRYSTALS

IS - 12-13

ER -