| Reversible and Covalent Binding of 5-(hydroxymethyl)-2-furaldehyde (HMF) with Lysine and selected Amino Acids. | |
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MedLine Citation:
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PMID: 21557617 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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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 [15Nα]lysine.2HCl, [15Nε]lysine.2HCl, [U-13C6]lysine.2HCl, [13C-6]lysine.2HCl and [U-13C6]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. The complete labeling studies along with structural analysis using appropriate synthetic precursors such as HMF 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 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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Authors:
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Plamen Y Nikolov; Varoujan Antranik Yaylayan |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-5-10 |
Journal Detail:
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Title: Journal of agricultural and food chemistry Volume: - ISSN: 1520-5118 ISO Abbreviation: - Publication Date: 2011 May |
Date Detail:
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Created Date: 2011-5-11 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 0374755 Medline TA: J Agric Food Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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