期刊
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
卷 59, 期 11, 页码 6099-6107出版社
AMER CHEMICAL SOC
DOI: 10.1021/jf200735c
关键词
lysine; proline; glycine; pent-4-en-1-amine; piperidine; HMF; vinylogous Amadori rearrangement and Schiff base adducts of HMF with amino acids
资金
- Natural Sciences and Engineering Research Council (NSERC) of Canada
The chemical reactivity of 5-(hydroxymethyl)-2-furaldehyde (HMF) with lysine, glycine, and proline was studied using isotope labeling technique. To confirm the formation of HMF adducts in glucose amino acid model systems, a useful strategy was developed in which products simultaneously possessing six glucose (HMF moiety) and any number of amino acid carbon atoms in addition to nitrogen were targeted using specifically labeled precursors such as [N-15(alpha)]lysine center dot 2HCl, [N-15(6)]lysine center dot 2HCl, [U-C-13(6)]lysine center dot 2HCl, [C-13(6)]lysine center dot 2HCl, and [U-C-13(6)]glucose in the case of lysine model system. In addition, model systems containing HMF and amino acids were also studied to confirm specific adduct formation. Complete labeling studies along with structural analysis using appropriate synthetic precursors such as I-IMF Schiff base adducts of piperidine and glycine have indicated that HMF generated in the glucose/amino acid model systems initially forms a Schiff base adduct that can undergo decarboxylation through an oxazolidin-5-one intermediate and form two isomeric decarboxylated Schiff bases. Unlike the Schiff bases resulting from primary amines or amino acids such as glycine or lysine, those resulting from secondary amino acids such as proline or secondary amines such as piperidine can further undergo vinylogous Amadori rearrangement, forming N-substituted 5-(aminomethyl)furan-2-carbaldehyde derivatives.
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