title: Studies on the Formation of Maillard and Caramelization Products from Glucosamine Incubated at 37 °C.
abstract: This experiment compared the in vitro degradation of glucosamine (GlcN), N-acetylglucosamine, and glucose in the presence of NH3 incubated at 37 °C in phosphate buffer from 0.5 to 12 days. The reactions were monitored with UV-vis absorption and fluorescence emission spectroscopies, and the main products of degradation, quinoxaline derivatives of α-dicarbonyl compounds and condensation products, were determined using UHPLC-UV and Orbitrap mass spectrometry. GlcN produced two major dicarbonyl compounds, glucosone and 3-deoxyglucosone, ranging from 709 to 3245 mg/kg GlcN and from 272 to 4535 mg/kg GlcN, respectively. 3,4-Dideoxyglucosone-3-ene, glyoxal, hydroxypyruvaldehyde, methylglyoxal, and diacetyl were also detected in lower amounts compared to glucosone and 3-deoxyglucosone. Several pyrazine condensation products resulting from the reaction between dicarbonyls and GlcN were also identified. This study determined that GlcN is a significantly unstable molecule producing a high level of degradation products at 37 °C.
authors.affiliation: Department of Agricultural, Food and Nutritional Science, University of Alberta, 4-10 Ag/For Building, Edmonton, Alberta, Canada T6G 2P5.
authors.forename: Yuliya
authors.initials: Y
authors.lastname: Hrynets
authors.affiliation: Department of Agricultural, Food and Nutritional Science, University of Alberta, 4-10 Ag/For Building, Edmonton, Alberta, Canada T6G 2P5.
authors.forename: Maurice
authors.initials: M
authors.lastname: Ndagijimana
authors.affiliation: Department of Agricultural, Food and Nutritional Science, University of Alberta, 4-10 Ag/For Building, Edmonton, Alberta, Canada T6G 2P5.
authors.forename: Mirko
authors.initials: M
authors.lastname: Betti
mesh_terms: D005944:Glucosamine / Q000737:chemistry*; D005947:Glucose / Q000737:chemistry; D006358:Hot Temperature; D007700:Kinetics; D015416:Maillard Reaction; D013058:Mass Spectrometry; D015394:Molecular Structure
chemical_list: D005947:Glucose; D005944:Glucosamine
keywords: Heyns compound; Maillard reaction; fructosazine; glucosamine; o-phenylenediamine (OPD); α-dicarbonyl compounds (α-DCs)