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On the role of the carbohydrate vs the lipid moieties in neoglycolipid self-organisation : Synthesis and liquid crystalline properties of two new families of carbohydrate-based amphiphiles

Abstract : In this study, we have synthesized two families of new carbohydrate-based amphiphilic derivatives: a series of alkyl glucoside ethers varying in terms of chain length and position on the sugar, and a series of glucosteroids varying in terms of alkyl spacer and, for the disutibstuted systems, in terms of alkyl side chain length. By the means of analytical methods, such as NMR spectroscopy, mass spectroscopy and elementary analysis, the structure of all the compounds was carefully established, as well as their purity. Their liquid crystalline behaviors were studied by the means of transmission light microscopy and differential scanning calorimetry. The two families of compounds which have been studied illustrate how much the behavior can be essentially related to polar interactions (H-bonding), therefore to the sugar moiety, for the ether series, or to hydrophobic interactions (lipid-lipid) in the glucosteroid series. In this latter series, preference for either steroid-stroid or steroid alkyl packing appears as an insight in understanding the behavior of complex lipids, showing potentially more than one conformational structure with important consequences on the supramolecular level, therefore to their potential biological role. This could be regarded as “lipid denaturation” by analogy to the protein denaturation. Also, when we see that compounds like the glycosteroids having an long chain ester -CAG, BbGL-I, are found to exist in Nature, and how much glycolipid-cholesterol interactions were recently shown to be critical in some biological processes, it is hoped that our observations can provide a new vision angle for the study of complex lipids and glycolipids. As a start to develop new probes targeting the “lipid raft” microdomain in membranes, we also explored a sequence towards carbohydrate laurdan hybrids. Further development of this strategy and evaluation of the biological properties is programmed within new collaborative projects.
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Rui Xu. On the role of the carbohydrate vs the lipid moieties in neoglycolipid self-organisation : Synthesis and liquid crystalline properties of two new families of carbohydrate-based amphiphiles. Other. INSA de Lyon, 2013. English. ⟨NNT : 2013ISAL0001⟩. ⟨tel-00940381⟩

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