THE BIOGENESIS OF ALKALOIDS: XXII. SOME INTERMEDIATE STEPS IN THE TRANSFORMATION OF TRYPTOPHAN TO GRAMINE

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Abstract
In germinating barley it is known that tryptophan is converted into gramine. In an attempt to find the intermediate steps in this conversion, it has been established that neither 3-indolylacetic acid, 3-indolylglyoxylic acid, 3-indolylaldehyde, nor 3-indolylacetamide (all labelled with 14C in the side chain) was a precursor of gramine. It has been shown, however, that both 3-indolylpyruvic acid and 3-indolylacrylic acid gave rise to radioactive gramine when fed to germinating barley. It is likely that these two acids constitute two intermediates in the pathway tryptophan–gramine.