title: Heat deterioration of phospholipids. VI. Clarification of mechanism for the new pseudo Maillard rearrangement reaction by using 2-aminoethyl dihydrogenphosphate.
abstract: 2,3-Dihydro-1H-imidazo[1,2-a]pyridine-4-ylium derivatives with UV absorption at 350 nm were formed by reaction of one molar of any sugar except 2-deoxysugars with two molar of phosphatidylethanolamines involving a new pseudo Maillard rearrangement reaction. To elucidate the reaction mechanism, 2-aminoethyl dihydrogenphosphate, which had a partially similar structural moiety to PE, was reacted with D-galactose. Though the UV absorption at 365 nm was not observed and the four pyridinium derivatives were also not formed in the reactant solution, the UV absorption at 286 nm and browning of the reactant solution were observed. From this reactant solution, two compounds with lambdamax at 283 nm and 297 nm were isolated and former was determined as 5-(hydroxymethyl)furfural (HMF) and later did as phosphoric acid mono{2-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]ethyl}ester (PMPEE), which is a new compound, respectively. Because reaction of PMPEE with PE leads to form the pyridinium derivatives, we concluded that a compound like PMPEE was one of intermediates in this new reaction.
authors.affiliation: Research and Development Section, Tsuji Oil Mill Co., Ltd., Matsusaka 515-2314, Japan. a.hayashi@tsuji-seiyu.co.jp
authors.forename: Akihito
authors.initials: A
authors.lastname: Hayashi
authors.forename: Yosuke
authors.initials: Y
authors.lastname: Yokoyama
authors.forename: Nobutoshi
authors.initials: N
authors.lastname: Hamaguchi
authors.forename: Takehiko
authors.initials: T
authors.lastname: Tsuji
authors.forename: Shin-Ichi
authors.initials: S
authors.lastname: Tebayashi
authors.forename: Chul-Sa
authors.initials: CS
authors.lastname: Kim
authors.forename: Hen-Sik
authors.initials: HS
authors.lastname: Koh
mesh_terms: D005662:Furaldehyde / Q000031:analogs & derivatives / Q000737:chemistry; D005690:Galactose / Q000737:chemistry; D006358:Hot Temperature; D015416:Maillard Reaction; D010755:Organophosphates / Q000737:chemistry*; D010743:Phospholipids / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry; D014466:Ultraviolet Rays
chemical_list: C526585:2-aminoethyl phosphate; D010755:Organophosphates; D010743:Phospholipids; D011758:Pyrroles; C526586:phosphoric acid mono(2-(2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl)ethyl)ester; C008046:5-hydroxymethylfurfural; D005662:Furaldehyde; D005690:Galactose