Stepwise synthesis of 2,3-&lt;i&gt;O&lt;/i&gt;-dipalmitoyl-D-glyceric acid and an in vitro evaluation of its cytotoxicity

Bioscience, Biotechnology, and Biochemistry

Kitamoto

Habe

2014

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mentioning

confidence: 99%

In vitro evaluation of glyceric acid and its glucosyl derivative, α-glucosylglyceric acid, as cell proliferation inducers and protective solutes

Bioscience, Biotechnology, and Biochemistry

Kitamoto

Habe

2014

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“…Other diacyl GAs with long acyl chains C16 or C18:2 were synthesized via the benzyl ester derivative of GA Fig. 2B 18,19 . The long acyl chains in the compounds resulted in low water solubility.…”

Section: Synthesis and Properties Of Acyl Gasmentioning

confidence: 99%

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

2021

J. Oleo Sci.

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Glyceric acid (GA) is an oxidative product of glycerol, and its d-isomer is obtained as a phytochemical from tobacco leaves and fruits of some plants. However, the production and applications of GA have not yet been fully investigated. In this review, recent developments in the microbial production of GA and its application to bio-related materials are summarized. The sodium salt of diacylated GA showed superior surface tension-lowering activity and antitrypsin activity. GA and its glucosyl derivative had positive effects on the viability and collagen production of skin cells in vitro, respectively. Glucosyl derivatives of GA showed protective effects against heat-induced protein aggregation. In addition, the microbial production of GA using raw glycerol as the starting material was investigated. The effect of methanol, a major impurity in raw glycerol, on GA production was investigated, and mutant strains to tolerate methanol in the culture were constructed. Enantioselective production of GA using newly isolated microbial strains has also been developed.

“…In particular, the acetic acid bacteria Acetobacter tropicalis induces chirality at C-2 of due to the hydrophobic nature of their long acyl chains. We previously synthesized diacyl GA with C16 and C18 acyl chain lengths, and investigated their biological properties [19][20][21]. The trypsin inhibition by these dioleoyl GA was demonstrably low, probably owing to its low water solubility [19].…”

Section: Introductionmentioning

confidence: 99%

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

Nagata

Kitamoto

et al. 2017

J Americ Oil Chem Soc

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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 (