Unveiling the γ-carboxyl role of glutamic acid in pyrazine formation from N-(1-deoxy-α-D-ribulos-1-yl)-glutamic acid: Mechanistic insights via integrated experimental and density functional theory approaches
文献类型： 外文期刊
作者： Zhan, Huan 1 ; Zhang, Li 1 ; Xu, Maosen 1 ; Yi, Xinyue 1 ; Li, Yangu 1 ; Zhao, Zongze 1 ; Diao, Yuduan 2 ;
作者机构： 1.Nanyang Inst Technol, Zhang Zhongjing Sch Chinese Med, Changjiang Rd 80, Nanyang 473004, Henan, Peoples R China
2.Shanghai Acad Agr Sci, Inst Anim Husb & Vet Sci, BeiDi Rd 2901, Shanghai 201106, Peoples R China
关键词： Amadori rearrangement product; Density functional theory; alpha-Dicarbonyls; gamma-Carboxyl deprotonation; Pyrazines; Strecker degradation
期刊名称：FOOD CHEMISTRY （ 影响因子：9.8； 五年影响因子：9.7 ）
ISSN： 0308-8146
年卷期： 2025 年 492 卷
页码：
收录情况： SCI
摘要： This study deciphers the gamma-carboxyl group's pivotal role in controlling pyrazine formation during thermal degradation of glutamic acid-derived Amadori rearrangement product (ARP). Integrated density functional theory (DFT) and pH-controlled experiments revealed gamma-carboxyl deprotonation (pKa = 4.29) initiates electronic effects that activate the amino group's nucleophilic capacity (-NH3+ to -NHS-like reactivity) remotely through orbital polarization and highest occupied molecular orbital (HOMO) energy elevation (-1.39 eV), enabling efficient alpha-dicarbonyl interactions. Comparative thermal treatments of Glu-derived ARP with supplementary amino acids revealed distinct flavor modulation pathways: lysine catalyzed alpha-dicarbonyl generation, boosting pyrazine yields, while glycine favored pyrrole derivatives via methylamine-mediated retro-aldol cleavage inhibition. pH-Dependent experiments confirmed that gamma-carboxyl deprotonation (pKa = 4.29) electronically activates the amino group even in its protonated state (-NH3+), bypassing direct deprotonation. The present work advances mechanistic understanding of Maillard reaction pathways and propose pH adjustment and amino acid supplementation as strategic tools for the regulation and improvement of ARP flavor formation.
- 相关文献
作者其他论文 更多>>
-
Muscle Characteristics Comparison Analysis Reveal Differences in the Meat Quality and Nutritional Components of Three Shanghai Local Pig Breeds
作者：Tu, Weilong;Wang, Hongyang;Zhang, Yingying;Huang, Ji;Diao, Yuduan;Zhou, Jieke;Tan, Yongsong;Tu, Weilong;Wang, Hongyang;Zhang, Yingying;Huang, Ji;Diao, Yuduan;Zhou, Jieke;Tan, Yongsong;Jiang, Wei;He, Chuan;Bai, Lan;Wu, Xiao
关键词：local pig breeds; meat quality traits; amino acids; texture; flavored nucleotide
-
Investigation of the Molecular Mechanism of Asthma in Meishan Pigs Using Multi-Omics Analysis
作者：Tu, Weilong;Wang, Hongyang;Zhang, Yingying;Huang, Ji;Diao, Yuduan;Zhou, Jieke;Tan, Yongsong;Li, Xin;Tu, Weilong;Wang, Hongyang;Zhang, Yingying;Huang, Ji;Diao, Yuduan;Zhou, Jieke;Tan, Yongsong;Tu, Weilong;Wang, Hongyang;Zhang, Yingying;Huang, Ji;Diao, Yuduan;Zhou, Jieke;Tan, Yongsong
关键词：Meishan pig; asthma; transcriptome; metabolome
-
The force of Zein self-assembled nanoparticles and the application of functional materials in food preservation
作者：Feng, Zhiruo;Shao, Bin;Yang, Qingli;Ju, Jian;Feng, Zhiruo;Shao, Bin;Yang, Qingli;Ju, Jian;Feng, Zhiruo;Shao, Bin;Yang, Qingli;Ju, Jian;Feng, Zhiruo;Shao, Bin;Yang, Qingli;Ju, Jian;Diao, Yuduan
关键词：Zein; Self-assembly force; Nanoparticles; Food packaging; Food preservation
-
Flavor characterization of pork cuts in Chalu black pigs using multi-omics analysis
作者：Zhang, Yingying;Diao, Yuduan;Huang, Ji;Wang, Hongyang;Tu, Weilong;Zhang, Jiajie;Zhou, Jieke;Tan, Yongsong;Zhang, Yingying;Diao, Yuduan;Huang, Ji;Wang, Hongyang;Tu, Weilong;Zhou, Jieke;Tan, Yongsong;Raza, Sayed Haidar Abbas;Zhang, Jiajie
关键词：Pork; Meat flavor; Muscle fiber type; Chinese indigenous pig; Multi-omics; Chalu black pigs
-
The development of chicken meat flavor from the interaction between Maillard reaction intermediates and enzymatically hydrolyzed-oxidized chicken fat
作者：Zhan, Huan;Jiang, Yanfang;Xu, Maosen;Cao, Dingyun;Lu, Wutong;Xin, Wenjing;Shen, Qingshan;Diao, Yuduan
关键词：Amadori rearrangement products; Enzymatically hydrolyzed-oxidized chicken fat; Maillard reaction; Lipid oxidation; Maillard-lipid interaction
-
The flavor properties of Amadori rearrangement products and their potentials in flavor replication of plant-based meat analogs: a review
作者：Zhan, Huan;Xin, Wenjing;Deng, Yang;Lin, Tao;Shen, Qingshan;Ma, Yanli;Hayat, Khizar;Diao, Yuduan
关键词：Amadori rearrangement products; plant-based meat analogs; flavor formation; Maillard-lipid interaction
-
The application of starch-based edible film in food preservation: a comprehensive review
作者：Wang, Yihui;Ju, Jian;Zhao, Fangyuan;Yang, Qingli;Wang, Yihui;Ju, Jian;Zhao, Fangyuan;Yang, Qingli;Wang, Yihui;Ju, Jian;Zhao, Fangyuan;Yang, Qingli;Wang, Yihui;Ju, Jian;Zhao, Fangyuan;Yang, Qingli;Diao, Yuduan
关键词：Food packaging; edible film; starch; modification; performance; food preservation
