Synthesis and Thermal Degradation Products of Two Amadori Derivatives
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摘要: 文章以D-果糖、L-苯丙氨酸和L-酪氨酸为原料合成两种Amadori衍生物:PDFD(二-O-异亚丙基-2,3:4,5-β-D-吡喃果糖基苯丙氨酸酯)和TDFD(二-O-异亚丙基-2,3:4,5-β-D-吡喃果糖基酪氨酸酯),用氢谱(1H NMR)、碳谱(13C NMR)以及高分辨质谱(HRMS)表征了物质的结构。采用热重(TG-DTG)、差示扫描量热法(DSC)、热裂解-气质(Py-GC/MS)联用技术研究了两种物质的热特性和热降解产物。结果表明,PDFD和TDFD最大质量损失率Tp值分别是273.3和340.5℃;两种物质均热降解产生大量的挥发性香味物质,如2-丁酮、苯甲醛、2-乙酰基呋喃、糠醛等,而且TDFD所需热降解温度较高且热降解产物含有酚类物质。对两种物质的热降解机理研究表明,保护糖环上的羟基在一定程度上可抑制吡喃糖环的降解,而氨基酸部分的降解几乎不受影响。该研究提供了一类基于Amadori化合物的香味前体物质,且为调控Amadori化合物热降解产物提供新思路。
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关键词:
- Amadori衍生物 /
- 热裂解-气质联用技术(Py-GC/MS) /
- 热重(TG-DTG) /
- 热降解
Abstract: Two Amadori derivatives,PDFD(di-O-isopropylidene-2,3:4,5-β-D-fructopyranosyl phenylalanine ester)and TDFD(di-O-isopropylidene-2,3:4,5-β-D-fructopyranosyl tyrosine ester),were synthesized based on D-fructose,L-phenylalanine and L-tyrosine,whose structures were characterized by 1H NMR,13C NMR and HRMS. TG-DTG,DSC and Py-GC/MS were conducted to investigate the thermal decomposition properties and the degradation products for PDFD and TDFD. The results showed that Tp of PDFD and TDFD with the largest mass loss rate were 273.3 and 340.5℃,respectively. Both derivatives could release aromatic compounds such as 2-butanone,benzaldehyde,2-acetylfuran and furfural. The degradation of TDFD needed higher temperature to provide phenolic compounds. The discussion of thermal degradation mechanisms for PDFD and TDFD showed that the protection of hydroxyl groups on the sugar ring could inhibit the degradation of glucopyranose moieties while the degradation of amino acids was not affected. This research provides a new kind of potential flavor precursors and offers a new strategy to control the degradation processes of Amadori compounds.
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