Effect of hydrogen-bonding interactions on the self-assembly formation of sodium N-(11-acrylamidoundecanoyl)-l-serinate, l-asparaginate, and l-glutaminate in aqueous solution

Self-assembly properties of some chiral N-palmitoyl amino acid surfactants in aqueous solution

“…These results indicate that no new chiral structures are formed through aggregation for the AAS studied here, contrary to N -palmitoylserine [24] and to some modified AAS [43,44]. It has been proposed for the latter two compounds that an interaction occurs between the carbonyl group of one amido group, and the hydrogen atom of the amido group of a second AAS, and so on, just like in peptides or in proteins.…”

“…It could be informative to extend this type of study to other AAS, in order to identify the best candidates in this group of compounds. The synthesis of new AAS derivatives designed for enhanced molecular interactions is also a promising research area, since small structural modifications have already been shown to produce interesting consequences [43,44].…”

“…This is the case for some acyl derivatives of aspartic acid, alanine, glycine and serine, which can form spherical vesicles, helical or cylindrical fibers, ribbons and tubules [38,39,43,44]. The latter structures can be of high interest, because they can be exploited as template for the preparation of nanostructured materials in view of technological applications [45,46].…”

Molecular bionics – engineering biomaterials at the molecular level using biological principles

“…Their assembling capability mainly depends on a structure-related parameter called hydrophiliclipophilic balance (HLB), i.e., an expression of the degree to which the molecule is hydrophilic or lipophilic. In the case of non-ionic surfactants, the hydrophilic and hydrophobic portions of the molecule can be linked either by ether, amide or ester bonds; hence, we can distinguish amongst alkyl ethers, alkyl amides and esters of fatty acids [114], although alkyl ether and ester surfactants are perhaps the most used for supramolecular applications (Figure 5b) [116][117][118][119].…”

Surfactant–Amino Acid and Surfactant–Surfactant Interactions in Aqueous Medium: a Review

“…The greater affinity for molecular interaction with amino acids was shown by CPB. Roy et al [108] probed the aggregation behaviour of 3 N-acyl amino acid surfactants, Na N-(11-acrylamidoundecanoyl)-L-serinate (SAUS), Na N-(11-acrylamidoundecanoyl)-Lasparaginate (SAUAS) and Na N-(11-acrylamidoundecanoyl)-L-glutaminate (SAUGL) in aqueous solution using surface tension, fluorescence, dynamic light scattering and transmission electron microscopic techniques. The amphiphiles initially formed flexible bilayer structures, which upon increasing the surfactant concentration transformed into closed spherical vesicles.…”