Amino Acid Catalysis of 2-Alkylfuran Formation from Lipid Oxidation-Derived α,β-Unsaturated Aldehydes
Amino Acid Catalysis of 2-Alkylfuran Formation from Lipid Oxidation-Derived α,β-Unsaturated Aldehydes
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DOI：
10.1021/jf202448v
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发表时间：
2011-10-26
影响因子：
6.1
通讯作者：
De Kimpe, Norbert
中科院分区：
文献类型：
--
作者：
Adams, An;Bouckaert, Capucine;De Kimpe, Norbert
详细研究了在干燥焙烧条件下，由相应的脂类衍生的α，β-不饱和醛生成2-烷基呋喃的反应。在α，β-不饱和醛中加入一种氨基酸可显著增加2-烷基呋喃的生成。多肽和蛋白质也能够催化相应的α，β-不饱和醛生成2-烷基呋喃。对2-烷基呋喃生成的进一步研究表明，反应需要氧化条件和自由基的参与。这样，2-甲基呋喃由2-戊烯醛合成，2-乙基呋喃由2-己烯醛合成，2-丙基呋喃由2-庚烯醛合成，2-丁基呋喃由2-辛烯醛合成，2-戊基呋喃由2-庚烯醛合成，2-己基呋喃由2-十烯醛合成。氨基酸对脂肪衍生的α，β不饱和醛形成2-烯丙基呋喃的影响是一个有趣的例子，说明了氨基酸在富含脂肪的食品的热加工过程中发生的众多化学反应中的复杂作用。
The formation of 2-alkylfurans from the corresponding lipid-derived alpha,beta-unsaturated aldehydes under dry-roasting conditions was investigated in detail. The addition of an amino acid to an alpha,beta-unsaturated aldehyde drastically increased 2-alkylfiiran formation. Peptides and proteins as well were able to catalyze 2-alkylfuran formation from the corresponding alpha,beta-unsaturated aldehydes. Further investigation of 2-alkylfuran formation showed the need of oxidizing conditions and the involvement of radicals in the reaction. This way, the formation of 2-methylfuran from 2-pentenal, 2-ethylfuran from 2-hexenal, 2-propylfuran from 2-heptenal, 2-butylfuran from 2-octenal, 2-pentylfuran from 2-nonenal, and 2-hexylfuran from 2-decenal was shown. The impact of amino acids on 2-allcylfuran formation from lipid-derived alpha,beta-unsaturated aldehydes represents an interesting example of the complex role of amino acids in the multitude of chemical reactions occurring during thermal processing of lipid-rich foods.