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REACTIONS BETWEEN AMINO ACIDS AND ORGANIC ACIDS: REACTION OF TRYPTOPHAN AND PYRUVIC ACID
Author(s) -
CHU N. T.,
CLYDESDALE F. M.
Publication year - 1976
Publication title -
journal of food science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.772
H-Index - 150
eISSN - 1750-3841
pISSN - 0022-1147
DOI - 10.1111/j.1365-2621.1976.tb00746_41_4.x
Subject(s) - pyruvic acid , tryptophan , chemistry , dicarboxylic acid , organic chemistry , organic acid , amino acid , biochemistry
A reaction between pyruvic acid and tryptophan, which produced yellow products, was found in this investigation. The isolation and identification of the compounds produced by this interaction were carried out by paper chromatography, UV, IR and NMR spectroscopy, and organic synthetic procedures. Four compounds were isolated: three were identitied as 1,2,3,4‐tetrahydroharman‐1,3‐dicarboxylic acid, an isomer of 1,2,3,4‐tetrahydroharman‐1,3‐dicarboxylic acid and harman. The compound which was not fully identified, was a yellow polymer. The decrease in concentration of pyruvic acid and tryptophan due to this interaction was analyzed by an automatic organic acid analyzer and an automatic amino acid analyzer. It was found that the ratio of pyruvic acid to tryptophan used in this reaction was approximately 1.6:1. This reaction was found to proceed via a 1:1 molecular reaction between tryptophan and pyruvic acid to form 1,2,3,4‐tetrahydroharman‐1,3‐dicarboxylic acid and its yellow isomer followed by the formation of a yellow polymer produced by the interaction of the yellow isomer of 1,2,3,4‐tetrahydroharman‐1,3‐dicarboxylic acid and pyruvic acid.