Molecular shape analysis of a Maillard reaction intermediate.
The Maillard (browning) reaction involving the polycondensation of sugars and amino acids is believed to be an important abiotic pathway for humic substance formation in nature. However, a major drawback is that the Maillard reaction is extremely slow at temperatures encountered under normal environmental conditions. In order to elucidate some details of this process molecular shape analysis was applied to investigate the initial reaction between D-glucose and glycine to form the Amadori compound fructosylglycine which is an intermediate product in the Maillard reaction. The structure of the Amadori compound was optimized at a quantum mechanical level and its ground state electron energy calculated. Molecular Iso-Density Contours (MIDCO's), electron density contour surfaces of constant electron density, were constructed for D-glucose, glycine and fructosylglycine in order to study the steric conditions for the reaction. The calculations indicate that the Amadori compound and water on one hand and the separate entities D-glucose and glycine on the other hand are very similar to each other in terms of their ground state energy. This agrees with the experimental observation that the reaction between D-glucose and glycine to form the Amadori compound is slow.
Jokic
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A
Department of Soil Science, University of Saskatchewan, Saskatoon, Saskatchewan, Canada S7N 5A8.
Zimpel
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Z
Huang
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PM
Mezey
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PG
D005947:Glucose / Q000737:chemistry; D005998:Glycine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015416:Maillard Reaction; D008958:Models, Molecular; D014867:Water / Q000737:chemistry
D014867:Water; C033188:fructosyl-glycine; D005947:Glucose; D005998:Glycine