Mechanochemistry of Strecker degradation: Interaction of glyoxal with amino acids.

Mechanochemistry is rapidly evolving into a versatile and green method for chemical synthesis. Due to its unique reaction conditions, ball milling of sugars and amino acids mainly leads to the formation of Amadori products with minimum degradation. In this study, we milled glyoxal trimer dihydrate with twenty proteogenic amino acids to demonstrate the formation of Strecker degradation products. HS-GC/MS studies indicated that Strecker degradation proceeded to selectively generate Strecker aldehyde and unsubstituted pyrazine as the major volatiles. Moreover, ESI/qToF/MS studies demonstrated for the first time the formation of the proposed key Strecker degradation intermediates, such as the condensation products and their decarboxylated products, indicating the similarity of the mechanism of Strecker reaction under ball milling to that proposed under hydrothermal reaction conditions. These studies provided supporting evidence that ball milling at ambient temperatures could be used as a novel synthetic approach to prepare precursors of aroma-active volatiles through Strecker degradation. Copyright © 2023 Elsevier Ltd. All rights reserved.

Citation

Haoran Xing, Varoujan Yaylayan. Mechanochemistry of Strecker degradation: Interaction of glyoxal with amino acids. Food chemistry. 2024 May 01;439:138071

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PMID: 38061296

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