Comparative Study of Interfacial and Biological Properties in d‐Glycerate‐Derived Surfactants

Abstract

did not form such associates. In tryptic hydrolysis studies using N α -benzoyl-dl-arginine-4-nitroanilide as a substrate, diC8GA-Na exhibited an inhibitory effect on trypsin (trypsin specific activity: 0.26 ± 0.045 U/mg-protein) greater than that of diC10GA-Na (0.39 ± 0.10 U/mg-protein), whereas diC6GA-Na did not show antitrypsin activity. These results show that diC8GA-Na was the most bioactive of the evaluated diacyl d-glycerate surfactants.Keywords d-Glyceric acid · Diacyl glycerate · Glycerol · Green surfactant · Interfacial property GA and produces enantiopure d-GA with a 99% enantiomer excess (ee) [11]. Multiple biological activities of d-GA as well as GA derivatives, including diacyl GA, glucosyl GA and so on, have been studied [14][15][16][17][18]. In 2001, GA esterified with long acyl chains (>C16) were reported to exhibit antitrypsin activity [18]. However, the further studies on their physical and biological properties have not been carried out Abstract The effects of hydrophobic chain length on the interfacial and biological properties of diacyl d-glyceric acid (d-GA) sodium salts were evaluated based on interfacial tension analyses, dynamic light scattering (DLS), and antitrypsin activity. Of the four synthesized d-GA-derived surfactants [dihexanoyl d-GA sodium salt (diC6GA-Na), dioctanoyl d-GA sodium salt (diC8GA-Na), didecanoyl d-GA sodium salt (diC10GA-Na), and dilauroyl d-GA sodium salt (diC12GA-Na)], only those with C6, C8, and C10 acyl chains were investigated because diC12GA-Na were insoluble at room temperature. Together with our previous results, surface tensions at the critical micelle concentration (CMC) were 33.9 mN/m for diC6GA-Na, 25.5 mN/m for diC8GA-Na, and 27.9 mN/m for diC10GA-Na. Evaluation of assembly size via DLS and optical microscopy revealed that diC8GA-Na and diC10GA-Na formed large associates with average sizes ranging from 50 to 200 μm at concentrations 4-5 times greater than their CMC, whereas diC6GA-Na Electronic supplementary material The online version of this article (

Application of Glyceric Acid to Bio-related Functional Materials and Improvement of Microbial Production

“…This is probably due to the difference in water solubility. Another water-soluble sodium salt of diacyl GAs, namely didecanoyl GA sodium salt, also had inhibitory effects on trypsin activity comparable to that of dioctanoyl GA sodium salt 21 . Additionally, sodium salts of dioctanoyl GA and didecanoyl GA form large associates with vesicle-like structures at high concentration 21 .…”

“…Another water-soluble sodium salt of diacyl GAs, namely didecanoyl GA sodium salt, also had inhibitory effects on trypsin activity comparable to that of dioctanoyl GA sodium salt 21 . Additionally, sodium salts of dioctanoyl GA and didecanoyl GA form large associates with vesicle-like structures at high concentration 21 . The understanding of this unique property of diacyl GAs will lead to new applications of GA diacyl surfactants.…”

“…In contrast, diacyl GAs with medium acyl chains C6 to C12 were synthesized by direct acylation of GA Fig. 2B 20,21 . Although the acid form of diacyl GAs with medium acyl chains showed little solubility in water, their sodium salts had good water solubility.…”