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Accelerated Degradation of DiXyl-α,ε-Lys-ARP via Interaction between Extra-Added Xylose and Monosubstituted Lys-ARPs during Maillard Reaction
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-07-22 , DOI: 10.1021/acs.jafc.4c05736 Han Zhang 1 , Heping Cui 1 , Xue Xia 1 , Shahzad Hussain 2 , Khizar Hayat 3 , Xiaoming Zhang 1 , Chi-Tang Ho 4
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-07-22 , DOI: 10.1021/acs.jafc.4c05736 Han Zhang 1 , Heping Cui 1 , Xue Xia 1 , Shahzad Hussain 2 , Khizar Hayat 3 , Xiaoming Zhang 1 , Chi-Tang Ho 4
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Lysine (Lys) is capable of forming a di-substituted Amadori rearrangement product (ARP) with xylose (Xyl), designated as diXyl-α,ε-Lys-ARP. DiXyl-α,ε-Lys-ARP degradation was characterized by two steps: Initially, Xyl-α- and Xyl-ε-Lys-ARP were formed through elimination or hydrolysis at specific Nα/Nε positions of the corresponding enol and imine intermediates, which were then further degraded to dicarbonyl compounds and regenerated Lys. Xyl-α- or Xyl-ε-Lys-ARP had a reactive free amino group (ε-NH2 or α-NH2), both of which were still highly reactive and able to undergo further reactions with Xyl. Therefore, the diXyl-α,ε-Lys-ARP/Xyl model system was established to explore the impact of extra-added Xyl on diXyl-α,ε-Lys-ARP degradation behavior. Extra-added Xyl remarkably affected the degradation pathway of diXyl-α,ε-Lys-ARP by capturing the Xyl-α- and Xyl-ε-Lys-ARP to regenerate diXyl-α,ε-Lys-ARP. This interaction between Xyl and mono-substituted Lys-ARPs promoted the shift of chemical equilibrium toward the degradation of diXyl-α,ε-Lys-ARP, thereby accelerating its degradation rate. This degradation was markedly facilitated by the elevated temperature and pH values. Interestingly, the yield of Xyl-α- and Xyl-ε-Lys-ARP was particularly dependent on the pH during diXyl-α,ε-Lys-ARP degradation. Xyl-ε-Lys-ARP was the dominant product at pH 5.5−7.5 while Xyl-α-Lys-ARP possessed a relatively higher content under weak alkaline conditions, which was related to the reactivities of the Nα/Nε positions under various reaction conditions.
中文翻译：
美拉德反应过程中额外添加的木糖和单取代的 Lys-ARP 之间的相互作用加速 DiXyl-α,ε-Lys-ARP 的降解
赖氨酸（Lys）能够与木糖（Xyl）形成二取代的阿马多里重排产物（ARP），命名为diXyl-α,ε-Lys-ARP。 DiXyl-α,ε-Lys-ARP 降解分为两个步骤：最初，Xyl-α- 和 Xyl-ε-Lys-ARP 通过在相应烯醇和亚胺的特定N α/ N ε 位置消除或水解而形成中间体，然后进一步降解为二羰基化合物并再生Lys。 Xyl-α-或Xyl-ε-Lys-ARP具有反应性游离氨基（ε-NH 2或α-NH 2 ），两者仍然具有高反应性并且能够与Xyl进行进一步反应。因此，建立了diXyl-α,ε-Lys-ARP/Xyl模型体系，探讨额外添加的Xyl对diXyl-α,ε-Lys-ARP降解行为的影响。额外添加的Xyl通过捕获Xyl-α-和Xyl-ε-Lys-ARP重新生成diXyl-α,ε-Lys-ARP，显着影响diXyl-α,ε-Lys-ARP的降解途径。 Xyl和单取代的Lys-ARPs之间的这种相互作用促进了化学平衡向diXyl-α,ε-Lys-ARP的降解方向移动，从而加速了其降解速率。升高的温度和 pH 值显着促进了这种降解。有趣的是，Xyl-α-和 Xyl-ε-Lys-ARP 的产率特别依赖于 diXyl-α,ε-Lys-ARP 降解过程中的 pH 值。 pH 5.5−7.5 时 Xyl-ε-Lys-ARP 为主要产物，而 Xyl-α-Lys-ARP 在弱碱性条件下含量相对较高，这与N α/ N ε 位点在各种条件下的反应活性有关。反应条件。
更新日期：2024-07-22
中文翻译：
美拉德反应过程中额外添加的木糖和单取代的 Lys-ARP 之间的相互作用加速 DiXyl-α,ε-Lys-ARP 的降解
赖氨酸（Lys）能够与木糖（Xyl）形成二取代的阿马多里重排产物（ARP），命名为diXyl-α,ε-Lys-ARP。 DiXyl-α,ε-Lys-ARP 降解分为两个步骤：最初，Xyl-α- 和 Xyl-ε-Lys-ARP 通过在相应烯醇和亚胺的特定N α/ N ε 位置消除或水解而形成中间体，然后进一步降解为二羰基化合物并再生Lys。 Xyl-α-或Xyl-ε-Lys-ARP具有反应性游离氨基（ε-NH 2或α-NH 2 ），两者仍然具有高反应性并且能够与Xyl进行进一步反应。因此，建立了diXyl-α,ε-Lys-ARP/Xyl模型体系，探讨额外添加的Xyl对diXyl-α,ε-Lys-ARP降解行为的影响。额外添加的Xyl通过捕获Xyl-α-和Xyl-ε-Lys-ARP重新生成diXyl-α,ε-Lys-ARP，显着影响diXyl-α,ε-Lys-ARP的降解途径。 Xyl和单取代的Lys-ARPs之间的这种相互作用促进了化学平衡向diXyl-α,ε-Lys-ARP的降解方向移动，从而加速了其降解速率。升高的温度和 pH 值显着促进了这种降解。有趣的是，Xyl-α-和 Xyl-ε-Lys-ARP 的产率特别依赖于 diXyl-α,ε-Lys-ARP 降解过程中的 pH 值。 pH 5.5−7.5 时 Xyl-ε-Lys-ARP 为主要产物，而 Xyl-α-Lys-ARP 在弱碱性条件下含量相对较高，这与N α/ N ε 位点在各种条件下的反应活性有关。反应条件。
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