Degradation of asparagine to acrylamide by carbonyl-amine reactions initiated by alkadienals

Positive interaction between amino and sulfhydryl groups for acrylamide removal

“…All other chemicals were purchased from Aldrich (Milwaukee, WI), Sigma (St. Louis, MO), Fluka (Buchs, Switzerland), or Merck (Darmstadt, Germany) and were of analytical grade. Granvogl and Schieberle (2006) with the modifications described by Hidalgo, Delgado, and Zamora (2009). Briefly, mixtures of the acrylamide (0.2 μmol) and the nucleophile (0-5 μmol) were singly homogenized with 0.063-0.200 mm silica gel 60 (300 mg) (Macherey-Nagel, Düren, Germany), 30 μL of 0.3 M buffer (sodium citrate for pH 3-6, and sodium phosphate for pH 6-8), and 150 μL of water, and heated under controlled atmosphere at 110-180°C in closed test tubes for 0-35 min.…”

Mitigating effect of piquin pepper (Capsicum annuum L. var. Aviculare) oleoresin on acrylamide formation in potato and tortilla chips

“…Numerous studies have studied the mechanisms by which acrylamide is formed in foods, and Maillard type reactions have been shown to be a major reaction pathway in which asparagine provides the backbone of the acrylamide molecule (Capuano & Fogliano, 2011;Mottram, Wedzicha, & Dobson, 2002;Stadler et al, 2002;Yaylayan, Wnorowski, & Locas, 2003). In addition, recent studies have identified other carbonyl compounds as potential contributors to asparagine degradation by reaction mechanisms similar to those initiated by carbohydrates (Capuano, Oliviero, Açar, Gökmen, & Fogliano, 2010;Hidalgo, Delgado, & Zamora, 2009;Zamora, Delgado, & Hidalgo, 2011a;Zamora & Hidalgo, 2008).…”

Amino phospholipids and lecithins as mitigating agents for acrylamide in asparagine/glucose and asparagine/2,4-decadienal model systems

“…Model reactions were carried out analogously to Granvogl and Schieberle (2006), with the modifications described by Hidalgo, Delgado, and Zamora (2009). Briefly, mixtures of asparagine (3.75 lmol), glucose or 2,4-decadienal (3.75 lmol), and the phospholipid or amino compound (0-3.75 lmol; 25 mg for soybean and egg lecithins) were singly homogenised with 0.063-0.200 mm silica gel 60 (300 mg) (Macherey-Nagel, Düren, Germany), 30 ll of 0.3 M sodium phosphate buffer, pH 7.0, and 150 ll of water, and heated under nitrogen at 180°C in closed test tubes for 10 min.…”