Computational studies on the maillard reaction of glucose

Date

4-2004

Degree

Bachelor of Science in Chemistry

College

College of Arts and Sciences (CAS)

Adviser/Committee Chair

Ernesto J Del Rosario

Abstract

SABARIAGA, JERILEE M. University of the Philippines Los Banos. April 2004. Computational Studies on the Maillard Reaction of Glucose/Fructose and Glycine in Water.

Adviser: Dr. Ernesto J. del Rosario

Maillard reaction model systems consisting of glucose or fructose as the sugar reactant and glycine as the amine reactant were simulated using Hyperchem software. Solvation was done by placing the solute in a periodic box with 195 to 210 water molecules based on the T1P3P model for water. Using molecular mechanics (AMBER or OPLS), geometry optimization was accomplished, while PM3 semiempirical method was used for single point calculations.

The rearrangement of the Amadori compound in the glucose-glycine system and the Heyns compound in the fructose-glycine system, as shown in the calculated heats of formation proves to be less favorable than dimerization. Straight-chain dimerization is favored over cyclic dimerization.

The computed HOMO-LUMO energy differences among the R (Rearrangement product), S (sugar reactant) and A (amine reactant) of the glucose-glycine and fructose-glycine were minimal for the R-A interaction. An R-A interaction involves nucleophilic addition of the amine to the carbonyl group of the rearrangement product, forming a carbon nitrogen double bond.

Among the proposed structures considered, the Yaylayan-Kaminsky (1998) structure is the most thermodynamically stable, followed by that of Kato and Tsuchida (1981), and then of Cammerer and Kroh (1995). The decreasing trend of the heat of formation of the oligomers as the number of monomers increases, favors the Yaylayan-Kaminsky mechanism.

Language

English

Location

UPLB Main Library Special Collections Section (USCS)

Call Number

Thesis

Document Type

Thesis

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