Isolation of D-4-chlorotryptophane derivatives as auxin-related metabolites from immature seeds of Pisum sativum.

Three active compounds which induce hypocotyl swelling in Phaseolus mungo were isolated from immature seeds of Pisum sativum. For purification of the compounds, our three-step procedure (counter-current distribution, Sephadex LH 20, and partition chromatography on silicic acid) were used. The chemical structures of two of the compounds were determined by synthesis to be α-N-carboethoxyacetyl- and α-N-carbomethoxyacetyl-D-4-chlorotryptophane. D-4-Chlorotryptophane is the first naturally occurring chlorinated amino acid found.