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2-L-天冬氨酸-2-脱氧-D-葡萄糖的合成及热裂解分析
引用本文:芦昶彤,陈芝飞,马宇平,侯佩,付瑜锋,郑峰洋,李成刚,孙志涛,高明奇,张展.2-L-天冬氨酸-2-脱氧-D-葡萄糖的合成及热裂解分析[J].食品科学,2018,39(5):99-105.
作者姓名:芦昶彤  陈芝飞  马宇平  侯佩  付瑜锋  郑峰洋  李成刚  孙志涛  高明奇  张展
作者单位:1.河南中烟工业有限责任公司技术中心,河南 郑州 450000;2.郑州轻工业学院食品与生物工程学院,河南 郑州 450002
基金项目:河南中烟工业有限责任公司2015年度科技攻关项目(YN2015002)
摘    要:以D-果糖和L-天冬氨酸单钾盐为原料合成了2-L-天冬氨酸-2-脱氧-D-葡萄糖,利用傅里叶变换红外光谱、 1H核磁共振(nuclear magnetic resonance,NMR)、13C NMR和高分辨率质谱技术进行结构表征。应用热重-微商 热重和在线裂解气相色谱/质谱联用技术分别研究了2-L-天冬氨酸-2-脱氧-D-葡萄糖的热失重和热裂解行为。采用 1,1-二苯基-2-三硝基苯肼(1-diphenyl-2-picrylhydrazyl,DPPH)自由基清除法和还原能力法对其体外抗氧化活性进 行测定。结果表明:合成产物为目标化合物;目标化合物的裂解温度为187.8 ℃,700 ℃时总失重达到91.26%;目 标化合物裂解产物的数量随温度的升高而增多,裂解产物包括杂环类、酮类、羧酸类、醛类、酚类、烯烃类、醇类 和芳烃类等化合物,裂解产物表现出烘焙香、甜香、焦甜香、可可香、花香和奶香等香韵;目标产物具有较强的 DPPH自由基清除能力和还原能力,是一种潜在的抗氧化剂。

关 键 词:2-L-天冬氨酸-2-脱氧-D-葡萄糖  Heyns重排反应  合成  热失重  热裂解  气相色谱-质谱法  香韵  

Synthesis and Pyrolysis of 2-L-Aspartic Acid-2-Deoxy-D-Glucose
LU Changtong,CHEN Zhifei,MA Yuping,HOU Pei,FU Yufeng,ZHENG Fengyang,LI Chenggang,SUN Zhitao,GAO Mingqi,ZHANG Zhan.Synthesis and Pyrolysis of 2-L-Aspartic Acid-2-Deoxy-D-Glucose[J].Food Science,2018,39(5):99-105.
Authors:LU Changtong  CHEN Zhifei  MA Yuping  HOU Pei  FU Yufeng  ZHENG Fengyang  LI Chenggang  SUN Zhitao  GAO Mingqi  ZHANG Zhan
Affiliation:1. Technology Center, China Tobacco Henan Industrial Co. Ltd., Zhengzhou 450000, China; 2. School of Food and Biological Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002, China
Abstract:2-L-Aspartic acid-2-deoxy-D-glucose was synthesized from D-fructose and L-aspartic acid monopotassium salt, and it was characterized by Fourier transform infrared spectroscopy, 1H nuclear magnetic resonance (NMR), 13C NMR and high resolution mass spectroscopy. The thermogravimetric behavior, thermal pyrolysis behavior and antioxidant activity of 2-L-aspartic acid-2-deoxy-D-glucose was investigated using thermo gravimetry-derivative thermo gravimetry (TG-DTG), on-line pyrolysis-gas chromatography-mass spectrometry (Py-GC-MS), and 1-diphenyl-2-picrylhydrazyl (DPPH) scavenging and reducing capacity assays, respectively. The results showed that the synthetic product was confirmed to be the target compound. The target compound has a pyrolysis temperature of 187.8 ℃ and a total weight loss of 91.26% at 700 ℃. The number of pyrolysis products from the compound increased with reaction temperature. The pyrolysis products included heterocyclic hydrocarbons, ketones, carboxylic acids, aldehydes, phenols, olefins, alcohols and aromatic hydrocarbons and other compounds, which had baking, sweet aroma, burnt-sweet, cocoa-like incense, floral and milky aroma notes. The synthetic product possessed strong DPPH free radical scavenging and reducing capacity and could be regarded as a potential antioxidant.
Keywords:2-L-aspartic acid-2-deoxy-D-glucose  Heyns rearrangement reaction  synthesis  thermal weight loss  pyrolysis  gas chromatography-mass spectrometry  aroma notes  
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