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Mass spectrometric detection and formation of D-amino acids in processed plant saps, syrups, and fruit juice concentrates

Patzold, R., Bruckner, H.
Journal of agricultural and food chemistry 2005 v.53 no.25 pp. 9722-9729
amino acids, enantiomers, stereochemistry, food analysis, gas chromatography, mass spectrometry, Maillard reaction, Amadori products, juice concentrates, grape juice, fruit juices, sap, maple syrup, syrups, heat treatment, carbohydrate content
Liquid and syrupy dietary saps and juices of plant origin, characterized by the presence of large quantities of saccharides (glucose, fructose, or sucrose) and containing amino acids, were analyzed for the presence of D-amino acids using enantioselective gas chromatography-mass spectrometry. D-Amino acids were detected in processed saps and juices of trees (maple, palm, birch), fruits (grape, apple, pear, pomegranate, date), and various other plants (agave, beetroot, sugar cane, carob). D-Ala was detected in all plant products and amounted to approximately 34% D-Ala (relative to L-Ala + D-Ala) in Canadian maple syrups, to approximately 13% in palm saps, and to 48 and 13% D-Ala, respectively, in concentrated grape juices (Spanish Arrope and Turkish Pekmez). Varying amounts and kinds of other D-amino acids were also detected. To test the hypothesis that racemization, that is, partial conversion of L-amino acids into their corresponding D-enantiomers, occurs at reversible stages of the Maillard reaction, the Amadori compound fructose-L-phenylalanine was synthesized. On heating at 200 degrees C for 5 (20) min, release of 10.8% (24.2%) D-Phe was detected. From the data it is concluded that the Amadori compounds formed in the course of the Maillard reaction are pecursors of D-amino acids in foodstuffs.