title: Synthesis and Characterization of Dioctanoyl Glycerate as Water-soluble Trypsin Inhibitor.
abstract: Glyceric acids (GAs) esterified with long acyl chains (> C16) exhibit antitrypsin activity (Folia Microbiol. 46, 21-23 (2001)). However, their hydrophobic nature, derived from the long acyl chains, has limited the number of studies on their physical and biological properties. To improve the water solubility of diacyl GAs, GA was esterified with octanoyl groups (C8), and its physical properties were investigated. Synthesized dioctanoyl GA was not water-soluble, whereas its sodium salt was. Surface tension measurements of dioctanoyl GA sodium salt (diC8GA-Na) in water revealed that the critical micelle concentration (CMC) was 0.82 mM, and surface tension at the CMC was 25.5 mN/m. Additionally, diC8GA-Na inhibited casein digestion by trypsin to a greater extent than dioleoyl GA. These data suggest that water-soluble diacyl GAs may have utility as surfactants and bioactive compounds.
authors.affiliation: Research Institute for Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST).
authors.forename: Shun
authors.initials: S
authors.lastname: Sato
authors.forename: Shota
authors.initials: S
authors.lastname: Nagata
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Imura
authors.forename: Tokuma
authors.initials: T
authors.lastname: Fukuoka
authors.forename: Tomotake
authors.initials: T
authors.lastname: Morita
authors.forename: Yutaka
authors.initials: Y
authors.lastname: Takahashi
authors.forename: Yukishige
authors.initials: Y
authors.lastname: Kondo
authors.forename: Dai
authors.initials: D
authors.lastname: Kitamoto
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Habe
mesh_terms: D002364:Caseins / Q000737:chemistry; D004951:Esterification; D005988:Glyceric Acids / Q000138:chemical synthesis* / Q000737:chemistry; D057927:Hydrophobic and Hydrophilic Interactions; D008823:Micelles; D012995:Solubility; D013500:Surface Tension; D013501:Surface-Active Agents; D014361:Trypsin Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D014867:Water
chemical_list: D002364:Caseins; D005988:Glyceric Acids; D008823:Micelles; D013501:Surface-Active Agents; D014361:Trypsin Inhibitors; D014867:Water