Characterization of a new Maillard type reaction product generated by heating 1-deoxymaltulosyl-glycine in the presence of cysteine.
The reaction between Amadori compounds and cysteine was investigated. When 1-deoxymaltulosyl-glycine (glycyl-fructosyl-glucose) was heated at 100 degrees C with cysteine in a neutral aqueous solution, a novel intermediate composed of 1-deoxyosone and cysteine was detected. NMR and mass spectrometry studies revealed the structure of the isolated intermediate to be 7,8a-dihydroxy-4a-methyl-8-(alpha-d-glucopyranosyloxy)hexahydro-5-oxa-4-thia-1-azanaphthalene-2-carboxylic acid. This intermediate easily generated isomaltol and acetylfuran as volatile compounds in 1 mol/L HCl at 100 degrees C.
Ota
Masafumi
M
Institute of Life Sciences and Food Research Laboratories, Ajinomoto Co. Inc., 1-1 Suzuki-cho, Kawasaki 210-8681, Japan. masafumi_oota@ajinomoto.com
Kohmura
Masanori
M
Kawaguchi
Hirokazu
H
D003545:Cysteine / Q000737:chemistry*; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D006358:Hot Temperature; D009682:Magnetic Resonance Spectroscopy; D015416:Maillard Reaction; D013058:Mass Spectrometry; D012996:Solutions; D021241:Spectrometry, Mass, Electrospray Ionization; D014835:Volatilization
C512563:1-deoxymaltulosyl-glycine; D012996:Solutions; D003545:Cysteine; D005998:Glycine