Synthesis and Characterization of a Novel Glycolipid with Glucosylglycerate as a Hydrophile Showing Protective Effects on Heat-induced Protein Denaturation

Shun Sato, Atsushi Kishimoto, Dai Kitamoto, Yutaka Takahashi, Yukishige Kondo, Hiroshi Habe

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Pages (from-to)493-499
Number of pages7
JournalJournal of oleo science
Volume68
Issue number5
DOIs
Publication statusPublished - 2019 May 1

Keywords

  • N-dodecyl-(R)-2-O-α-D-glucopyranosylglyceric acid amide
  • glyceric acid
  • glycerol
  • surfactant
  • α-glucosylglycerate

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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