title: Maillard reaction of D-glucose: identification of a colored product with hydroxypyrrole and hydroxypyrrolinone rings connected by a methine group.
abstract: Investigation of the colored products formed by the reaction of d-glucose with butylammonium acetate has been extended. The previously unknown 1-N-butyl-4-hydroxy-5-methyl-2-(N-butyl-3-hydroxy-5-(2-hydroxyethyl)pyrrolyl-2-methylidene)-2H-pyrrolin-3-one (2a) was isolated from the reaction mixture and identified after acylation by spectroscopic data. Butylaminammonium acetate was used as a model compound representing the lysine side chains of proteins.
authors.affiliation: Department of Pharmacy, University of Munich, Butenandtstrasse 7, 81377 Munich, Germany.
authors.forename: Holger
authors.initials: H
authors.lastname: Lerche
authors.forename: Monika
authors.initials: M
authors.lastname: Pischetsrieder
authors.forename: Theodor
authors.initials: T
authors.lastname: Severin
mesh_terms: D000215:Acylation; D003124:Colorimetry; D005947:Glucose / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015416:Maillard Reaction; D011753:Pyrones / Q000032:analysis* / Q000737:chemistry / Q000302:isolation & purification; D013053:Spectrophotometry
chemical_list: C477021:1-N-butyl-4-hydroxy-5-methyl-2-(N-butyl-3-hydroxy-5-(2-hydroxyethyl)pyrrolyl-2-methylidene)-2H-pyrrolin-3-one; D011753:Pyrones; D005947:Glucose