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Formation of Furan, Furan-derivatives and Nitrogen-containing Compounds from the Thermal Interactions of Glucose with Glutamine, Glutamic acid, Glutaric acid or Ammonium sulfate

Title
Formation of Furan, Furan-derivatives and Nitrogen-containing Compounds from the Thermal Interactions of Glucose with Glutamine, Glutamic acid, Glutaric acid or Ammonium sulfate
Authors
이수진
Issue Date
2009
Department/Major
대학원 식품공학과
Publisher
이화여자대학교 대학원
Degree
Master
Advisors
김영석
Abstract
Ammonia, a source of nitrogen-containing compounds or an accelerant of Maillard reaction, can be released from deamination or deamidation of amino acids. Glutamine, glutamic acid and glutaric acid have similar carbon skeletons but have different numbers of nitrogen component in their structure. In this study, glutamine, glutamic acid, glutaric acid, or ammonium sulfate was reacted with/without glucose to investigate the effects of ammonia on the formation of furan, furan-derivatives and nitrogen-containing compounds. In general, non-aqueous condition was favorable for the release of ammonia, and the formation of furan, furan-derivatives, and nitrogen-containing compounds compared to aqueous condition. Pyrolysis of single compounds with similar carbon skeletons (glutamine, glutamic acid and glutaric acid) generated similar amount of furan in both thermal conditions (aqueous/non-aqueous). In aqueous condition, there were no significant differences of furan amount between glucose system and ammonium sulfate-glucose system, while ammonium sulfate-glucose system generated high amount of furan in non-aqueous condition. Glutamine-glucose system, glutamic acid-glucose system produced high contents of furan, but there were no significant differences between them. Out of these, glutamine-glucose system generated lower amount of furan-derivatives, but higher amount of nitrogen-containing compounds. According to ^(13)C-labeling study, fragment patterns of glutamine-glucose system and glutamic acid-glucose system were similar, but different from glutaric acid-glucose system. The characteristic patterns of glutaric acid-^(13)C_(6)- glucose system were high amount of unlabeled furan in aqueous condition, but the absence of unlabeled furan in dry condition, though glutaric acid is able to produce furan for itself. In conclusion, ammonia could affect the formation of furan, furan-derivatives and nitrogen-contining compounds and catalyze various fragment reactions.;질소함유 화합물을 구성하거나 Maillard reaction를 촉진하는 역할을 한다고 알려져 있는 암모니아는 아미노산의 탈아미노반응이나 탈아마이드반응에 의해 방출된다. Glutamine, glutamic acid, glutaric acid는 유사한 탄소골격을 가지고 있지만 구조 내 질소 구성의 수가 다르다. 이 연구에서는 암모니아가 퓨란, 퓨란유도체, 질소함유화합물에 미치는 영향을 알아보기 위해 glutamine, glutamic acid, glutaric acid 혹은 ammonium sulfate를 glucose와 함께/혹은 각각 반응하였다. 일반적으로 물이 없는 조건은 물이 있는 조건에 비해 암모니아 방출이나 퓨란, 퓨란유도체, 질소함유 화합물의 형성에 보다 적합한 조건인 것으로 나타났다. 탄소골격이 같은 단일 화합물 (glutamine, glutamic acid, glutaric acid)의 열분해에 의한 퓨란생성량은 두 가열조건에서 유사했으며, glucose, ammonium sulfate-glucose system에서 생성되는 퓨란의 양을 비교해보았을 때, 물이 있는 조건에서는 유의적인 차이가 없었으나 물이 없는 조건에서는 ammonium sulfate-glucose system에서 높은 양을 나타내었다. Glutamine-glucose system과 glutamic acid-glucose system에서는 양 system에서 높은 양의 퓨란이 생성되었으나 system 간의 유의적인 차이는 없었으며, glutamine-glucose system이 glutamic acid-glucose system에 비해 퓨란유도체의 함량이 낮았으나 질소함유화합물의 생성이 높았다. ^(13)C-labeling 연구 방법을 사용시 glutamine-glucose system과 glutamic acid-glucose system의 fragment 패턴은 유사하였으나 glutaric acid-glucose system의 fragment 패턴과는 달랐다. Glutaric acid-^(13)C_(6)-glucose system을 반응시켰을 때, 특징적으로 물이 있는 조건에서 unlabeled 퓨란이 높게 생성되었으나 물이 없는 조건에서는 glutaric acid 홀로 퓨란을 생성할 수 있음에도 불구하고 unlabeled 퓨란이 생성되지 않았다. 결론적으로 암모니아는 여러가지 fragment 반응을 촉진하여 퓨란, 퓨란유도체, 질소함유 화합물의 형성에 영향을 미치는 것으로 보인다.
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