1120-99-6Relevant articles and documents
Detection of α-Dicarbonyl compounds in Maillard reaction systems and in vivo
Glomb,Tschirnich
, p. 5543 - 5550 (2001)
α-Dicarbonyl compounds are of major interest in food chemistry and biochemistry as important precursors of, for example, protein modifications and flavor. Due to their high reactivity most of the published structures were identified and quantitated as stable derivatives after reaction with trapping reagents. However, the present study showed for the first time that the trapping reagents are of dramatic impact on the final qualitative and quantitative α-dicarbonyl spectrum. As important representatives, aminoguanidine and o-phenylenediamine were used to compare trapping characteristics and to monitor the dicarbonyl structures arising from the degradation of an Amadori compound. Dicarbonyl structures with a reductone moiety could not be or were only insufficiently detected by slow-reacting reagents such as aminoguanidine. On the other hand, fast-reacting chemicals such as o-phenylenediamine imposed high oxidative stress on the investigated system and led to enhanced or false positive formation of dicarbonyl compounds generated by oxidative pathways.
Preparation method of 3-amino-1, 2, 4-triazine
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Paragraph 0019-0024, (2021/03/13)
The invention discloses a preparation method of 3-amino-1, 2, 4-triazine, which comprises the following steps of adding aminoguanidine carbonate and water into a reaction vessel, adding an organic solvent, slowly dropwise adding a glyoxal water solution, reacting at -10-60 DEG C, and filtering, concentrating and crystallizing after the reaction to obtain the 3-amino-1, 2, 4-triazine. According tothe preparation method of the 3-amino-1, 2, 4-triazine, a small amount of solvent is added into an aqueous solution, and aminoguanidine carbonate reacts with glyoxal to obtain the 3-amino-1, 2, 4-triazine, so that the preparation method has the advantages of high production efficiency, high yield, simplicity and convenience in operation, safety and environmental friendliness, and can be suitable for industrial large-scale production.
Strain-Promoted Reaction of 1,2,4-Triazines with Bicyclononynes
Horner, Katherine A.,Valette, Nathalie M.,Webb, Michael E.
supporting information, p. 14376 - 14381 (2015/10/05)
Strain-promoted inverse electron-demand Diels-Alder cycloaddition (SPIEDAC) reactions between 1,2,4,5-tetrazines and strained dienophiles, such as bicyclononynes, are among the fastest bioorthogonal reactions. However, the synthesis of 1,2,4,5-tetrazines is complex and can involve volatile reagents. 1,2,4-Triazines also undergo cycloaddition reactions with acyclic and unstrained dienophiles at elevated temperatures, but their reaction with strained alkynes has not been described. We postulated that 1,2,4-triazines would react with strained alkynes at low temperatures and therefore provide an alternative to the tetrazine cycloaddition reaction for use in in vitro or in vivo labelling experiments. We describe the synthesis of a 1,2,4-triazin-3-ylalanine derivative fully compatible with the fluorenylmethyloxycarbonyl (Fmoc) strategy for peptide synthesis and demonstrate its reaction with strained bicyclononynes at 37°C with rates comparable to the reaction of azides with the same substrates. The synthetic route to triazinylalanine is readily adaptable to late-stage functionalization of other probe molecules, and the 1,2,4-triazine-SPIEDAC therefore has potential as an alternative to tetrazine cycloaddition for applications in cellular and biochemical studies.
