Recent progress in the synthesis of carbohydrate-based amphiphilic materials: the examples of sucrose and isomaltulose

Role of hydroxyl group on the mesomorphism of alkyl glycosides: synthesis and thermal behavior of alkyl 6-deoxy-β-d-glucopyranosides

“…Both the ␣-and ␤-anomers of alkyl glucopyranosides exhibit a wide range of enantiotropic SmA phase, with the alkyl chain length from C 7 to C 16 . The mesomorphism in carbohydrate amphiphiles is primarily due to the microphase segregation of hydrophilic and hydrophobic moieties (Queneau et al, 2008;Boullanger, 1997; van Doren and Wingert, 1994). The molecules form a bilayer structure in which the hydrophilic sugar head groups are held together by the strong hydrogen bonding and the hydrophobic alkyl chain bound together by the weak van der Waal forces (van Doren and Wingert, 1991).…”

“…Self-organizing properties of glycolipids, mediated by a host of non-covalent interactions, lead to their mesomorphic behavior Queneau et al, 2008;Goodby et al, 2007;Vill and Hashim, 2002; van Doren et al, 2000;Goodby et al, 1998;Jeffrey, 1986;Paleos and Tsiourvas, 1995). Dynamically fluctuating hydrogen-bonded network and van der Waal interactions are primary among the non-covalent interactions and, in amphiphilic glycolipids, these interactions result in a microphase segregation of the hydrophilic and lyophilic regions upon aggregation (Boullanger, 1997; van Doren and Wingert, 1994).…”

Self-assembly of 6-O- and 6′-O-hexadecylsucroses mixture under aqueous conditions

“…In the case of palmitic esters, a significant change in the size of the aggregates was observed depending on the position, whereas no effect was observed for shorter chains. 8 On the basis of the above viewpoints, we have recently studied the synthesis and self-assembly properties of new sucrose-based amphiphiles having molecular structures different from the sucrose fatty acid esters. These investigations were carried out to reveal fundamental aspects of the new amphiphiles for future practical applications.…”

Interactions between Bio-Based Compounds and Cyclodextrins

“…However, nowadays, several successful synthesis routes are well established, and numerous types of natural surfactants are known and available, even on a commercial scale [38]. Nowadays, carbohydrate-based surfactants (CBS) are among the most important classes of amphiphilic compounds [39][40][41]. Their structure results from the combination of sugar and lipids, naturally biosynthesized within living cells or, alternatively, synthetically prepared by sequential reactions using carbohydrate and fatty materials.…”