Comparison of 2-acetylfuran formation between ribose and glucose in the Maillard reaction.
Sugar type is a major factor regulating the reaction rates and pathways in Maillard reaction. Ribose and glucose were used to compare their reactivities and pathways of 2-acetylfuran formation. A stable isotope labeling method was used to study their reactivity. A 1:1 mixture of [(13)C(6)]glucose and unlabeled ribose (or other unlabeled sugar) was reacted with proline at 145 degrees C for 40 min. The reactivity of each sugar was revealed by the ratio of isotopomers. The reactivity of sugars in 2-acetylfuran formation decreased in the order ribose, fructose, glucose, rhamnose, and sucrose. This method simplified the reaction system and the calculation process and gave a direct comparison of reactivity as seen via mass spectrum. The difference between glucose and ribose in 2-acetylfuran formation was that glucose could form 2-acetylfuran directly from cyclization of its intact carbon skeleton, whereas ribose first underwent degradation into fragments before forming a six-carbon unit leading to 2-acetylfuran. In the presence of cysteine, ribose could not generate 2-acetylfuran at a detectable level. When ribose was reacted with glycine, formaldehyde generated from glycine combined with ribose to form 2-acetylfuran. In other amino acids, a symmetric structure of the ribose intermediate was formed, making fragmentation more complicated.
Wang
Yu
Y
Department of Food Science, Rutgers University, New Brunswick, New Jersey 08901-8520, USA.
Ho
Chi-Tang
CT
D002247:Carbon Isotopes / Q000032:analysis; D005663:Furans / Q000032:analysis*; D005947:Glucose / Q000737:chemistry*; D015416:Maillard Reaction; D012266:Ribose / Q000737:chemistry*
D002247:Carbon Isotopes; D005663:Furans; D012266:Ribose; D005947:Glucose; C039669:2-acetylfuran