TY - JOUR
T1 - Synthesis and Characterization of a Novel Glycolipid with Glucosylglycerate as a Hydrophile Showing Protective Effects on Heat-induced Protein Denaturation
AU - Sato, Shun
AU - Kishimoto, Atsushi
AU - Kitamoto, Dai
AU - Takahashi, Yutaka
AU - Kondo, Yukishige
AU - Habe, Hiroshi
PY - 2019/5/1
Y1 - 2019/5/1
N2 - A novel glycolipid featuring a glucosylglycerate moiety as a polar head group was synthesized in two steps from sucrose, glycerate, and N-dodecylamine. Glucosylglyceric acid was formed from sucrose and glyceric acid using sucrose synthase as a catalyst, followed by condensation with N-dodecylamine using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as a condensing agent. A white solid compound was recovered with a yield of 21% after purification by hydrophobic column chromatography. The structure and purity of the isolated compound, identified as N-dodecyl glucosylglyceric acid amide (aGGA), were confirmed by 1H and 13C nuclear magnetic resonance and liquid chromatography-electrospray ionization-mass spectrometry. aGGA was soluble in several polar solvents, including acetone, dimethyl formamide, and short chain alcohols. The dissolution of aGGA in water reduced the surface tension to 27.8 mN m-1 at a critical micellar concentration of 1.57 × 10-4 M. In addition, the presence of aGGA at concentrations as low at 0.68 mM protected egg white from heat-induced denaturation. These results suggest that aGGA could be useful as a protein-protecting surfactant.
AB - A novel glycolipid featuring a glucosylglycerate moiety as a polar head group was synthesized in two steps from sucrose, glycerate, and N-dodecylamine. Glucosylglyceric acid was formed from sucrose and glyceric acid using sucrose synthase as a catalyst, followed by condensation with N-dodecylamine using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as a condensing agent. A white solid compound was recovered with a yield of 21% after purification by hydrophobic column chromatography. The structure and purity of the isolated compound, identified as N-dodecyl glucosylglyceric acid amide (aGGA), were confirmed by 1H and 13C nuclear magnetic resonance and liquid chromatography-electrospray ionization-mass spectrometry. aGGA was soluble in several polar solvents, including acetone, dimethyl formamide, and short chain alcohols. The dissolution of aGGA in water reduced the surface tension to 27.8 mN m-1 at a critical micellar concentration of 1.57 × 10-4 M. In addition, the presence of aGGA at concentrations as low at 0.68 mM protected egg white from heat-induced denaturation. These results suggest that aGGA could be useful as a protein-protecting surfactant.
KW - N-dodecyl-(R)-2-O-α-D-glucopyranosylglyceric acid amide
KW - glyceric acid
KW - glycerol
KW - surfactant
KW - α-glucosylglycerate
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U2 - 10.5650/jos.ess19044
DO - 10.5650/jos.ess19044
M3 - Article
C2 - 30971645
AN - SCOPUS:85065679591
VL - 68
SP - 493
EP - 499
JO - Journal of Oleo Science
JF - Journal of Oleo Science
SN - 1345-8957
IS - 5
ER -