title: Biochemical synthesis of novel, self-assembling glycolipids from ricinoleic acid by a recombinant α-glucosidase from Geobacillus sp.
abstract: To explore a novel glycolipid, we performed biochemical reactions using a recombinant α-glucosidase from Geobacillus sp. which shows excellent transglycosylation reaction to hydroxyl groups in a variety of compounds. Two different glycolipids (GL-1 and GL-2) were prepared from ricinoleic acid using a recombinant α-glucosidase from Geobacillus sp. The molecular structure of GL-1 was confirmed as 12-O-α-D-glucopyranosyl-9-hexadecenoic acid by 1D and 2D NMR analyses. According to MALDI-TOF/MS, GL-1 and GL-2 showed single major peaks at m/z 483.82 and 645.97, respectively. The peaks corresponded to the [M + Na](+) ions of the glycolipids. GL-2 was estimated as 12-O-α-D-glucopyranosyl-(4'-O-α-glucopyranosyl)-9-hexadecenoic acid. Light polarization microscopy revealed that GL-2 easily formed self-assembled vesicles in aqueous solution.
authors.affiliation: Institute of Biogeosciences, Japan Agency for Marine-Earth Science and Technology (JAMSTEC), 2-15, Natsushima-cho, Yokosuka, 237-0061, Japan. konishi-masaaki@jamstec.go.jp
authors.forename: Masa-aki
authors.initials: MA
authors.lastname: Konishi
authors.forename: Tokuma
authors.initials: T
authors.lastname: Fukuoka
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Shimane
authors.forename: Kozue
authors.initials: K
authors.lastname: Mori
authors.forename: Yuriko
authors.initials: Y
authors.lastname: Nagano
authors.forename: Yukari
authors.initials: Y
authors.lastname: Ohta
authors.forename: Dai
authors.initials: D
authors.lastname: Kitamoto
authors.forename: Yuji
authors.initials: Y
authors.lastname: Hatada
mesh_terms: D056506:Geobacillus / Q000201:enzymology*; D006017:Glycolipids / Q000096:biosynthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D011994:Recombinant Proteins / Q000302:isolation & purification / Q000378:metabolism; D012277:Ricinoleic Acids / Q000378:metabolism*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D000520:alpha-Glucosidases / Q000302:isolation & purification / Q000378:metabolism*
chemical_list: D006017:Glycolipids; D011994:Recombinant Proteins; D012277:Ricinoleic Acids; D000520:alpha-Glucosidases; C030521:ricinoleic acid