Maillard Mimetic Food-Grade Synthesis of N-(β-d-Deoxyfructos-1-yl)-l-glutamic Acid and N-(β-d-Deoxyfructos-1-yl)-β-alanyl-l-histidine by a Combination of Lyophilization and Thermal Treatment.,Journal of Agricultural and Food Chemistry

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Maillard Mimetic Food-Grade Synthesis of N-(β-d-Deoxyfructos-1-yl)-l-glutamic Acid and N-(β-d-Deoxyfructos-1-yl)-β-alanyl-l-histidine by a Combination of Lyophilization and Thermal Treatment.
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2020-07-02 , DOI: 10.1021/acs.jafc.0c03009
Jianan Zhang _{1,

2} , Mouming Zhao ₁ , Nanxi Gao ₁ , Guowan Su ₁ , Baoguo Sun ₃ , Jiahui Zhang ₄ , Chi-Tang Ho ₂

Affiliation

A typical glycoconjugate of glutamic acid, namely, N-(β-d-deoxyfructos-1-yl)-l-glutamic acid, was successfully synthesized as the primary isomer in a yield of 96.08% using a food-grade preparation method, and its chemical structure was clearly demonstrated by mass spectrometry and 1D/2D NMR. The reaction kinetics of glucose and glutamic acid were systematically studied to investigate the effect of lyophilization and thermal treatment on the conversion of reactants to their corresponding Amadori rearrangement product (ARP). Interestingly, besides the initial pH value, temperature, and heating time, the initial concentration of glutamic acid also influenced the final yield because intramolecular dehydration occurred at the same time, competing with the Maillard reaction and degrading reaction. Moreover, a similar Amadori compound of carnosine was also prepared in a yield of about 66.38% and the yield could be further improved to 95% after condition optimization. One major isomer of the corresponding ARP of the peptide was confirmed to be N-(β-d-deoxyfructos-1-yl)-β-alanyl-l-histidine by structure characterization, indicating that this is a good method to prepare the N-(β-d-deoxyfructos-1-yl)-amino acid/peptide.

中文翻译：

N-（β-d-脱氧果糖-1-基）-1-谷氨酸和N-（β-d-脱氧果糖-1-基）-β-丙氨酰基-1-组氨酸的美拉德模拟食品级合成冻干和热处理的过程。

谷氨酸的典型糖缀合物，即ñ - （β- d -deoxyfructos -1-基） -升用食品级制备方法成功合成了β-谷氨酸作为主要异构体，收率为96.08％，其化学结构已通过质谱和1D / 2D NMR明确证实。系统地研究了葡萄糖和谷氨酸的反应动力学，以研究冻干和热处理对反应物转化为相应的Amadori重排产物（ARP）的影响。有趣的是，除了初始的pH值，温度和加热时间外，谷氨酸的初始浓度还影响了最终的收率，因为分子内的脱水同时发生，与美拉德反应和降解反应竞争。此外，还以约66的产率制备了类似的肌肽的Amadori化合物。条件优化后，收率可达38％，收率可进一步提高到95％。确认该肽的相应ARP的一种主要异构体是通过结构表征获得N-（β- d-脱氧果糖-1-基）-β-丙氨酰基-1-组氨酸，表明这是制备N-（β- d-脱氧果糖-1-基）-氨基的良好方法酸/肽。

更新日期：2020-07-29

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