食品科学2024，Vol.45Issue(10)：62-71,10.DOI:10.7506/spkx1002-6630-20230515-128
糖熏色素5-(葡萄糖基-α-1-6-葡萄糖)-羟甲基糠醛形成机理的量子化学计算
Quantum Chemical Calculation of the Formation Mechanism of the Sugar Smoking Pigment 5-(α-D-Glucopyranosyl-(1-6)-α-D-glucopyranosyloxymenthyl)-2-furancarboxaldehyde
摘要
Abstract
In order to explore the formation pathways of 5-(α-D-glucopyranosyl-(1-6)-α-D-glucopyranosyloxymenthyl)-2-furancarboxaldehyde(5-GGMF),a pigment formed during the process of sugar smoking,the thermal decomposition reaction site of sucrose,the dehydration reaction modes between glucose and 5-hydroxymethylfurfural(5-HMF)and between two molecules of glucose,and the formation pathways of 5-HMF and 5-GGMF were analyzed by quantum chemical calculation.The results showed that the initial position of thermal decomposition of sucrose was the cleavage of fructosyl-oxygen bond.van der Waals force played a leading role in the complexes formed by the interaction between glucose and 5-HMF and between two molecules of glucose,and the intermolecular dehydration reaction was promoted by strong hydrogen bonding.The formation of 5-HMF from the glucose moiety formed after the pyrolysis of sucrose needed more activation energy than from the fructose moiety formed with a lower reaction rate,indicating that the fructose moiety was more prone to form 5-HMF.Among the two formation pathways of 5-HMF from the fructose moiety,pathway 5 was more prone to occur than pathway 4,because pathway 5 showed obvious advantages in energy and reaction kinetics.In the formation pathways of 5-GGMF from sucrose,the energy barrier of the transglycosylation pathway was overall lower,which was more favorable than the disaccharide dehydration and trisaccharide dehydration pathways.Among them,pathway C2,including three steps:the pyrolysis of sucrose to produce fructose and glucose,the reaction of glucose with 5-HMF to form 5-glucosyloxymethylfurfural(5-GMF),and the reaction of 5-GMF with a molecule of free glucose to produce 5-GGMF,was most conducive to the generation of 5-GGMF from both an energy barrier and kinetic perspective.The results of this study can provide a theoretical basis and reference for controlling and intervening in the color of sugar smoked products in the future.关键词
糖熏色素/5-(葡萄糖基-α-1-6-葡萄糖)-羟甲基糠醛/量子化学/密度泛函理论Key words
sugar smoking pigment/5-(α-D-glucopyranosyl-(1-6)-α-D-glucopyranosyloxymenthyl)-2-furancarboxaldehyde/quantum chemistry/density functional theory分类
轻工业引用本文复制引用
叶国庆,牛玉敏,范朝侠,杨慧,刘登勇..糖熏色素5-(葡萄糖基-α-1-6-葡萄糖)-羟甲基糠醛形成机理的量子化学计算[J].食品科学,2024,45(10):62-71,10.基金项目
辽宁省"揭榜挂帅"科技计划(重点)项目(2022JH1/10900011 （重点）
2021JH1/10400033) （）
