β-Pyrazol-1-ylalanine, an amino acid from water-melon seeds (Citrullus vulgaris)

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Abstract
A heterocyclic amino acid, (-)-[beta]-pyrazol-1-ylalanine, was isolated from the seed of watermelon (Citrullus vulgaris) and its structure, confirmed by comparison with synthetic material. DL-[beta]-Pyrazol-1-ylalanine was synthesized in poor yield by condensation of silver pyrazole with the methyl ester of [beta]-chloroalanine hydrochloride. The amino acid was decomposed by treatment with 55% (w/w) hy-driodic acid to give alanine and a substance tentatively identified as an iodopyrazole. The distribution and possible method of biogenesis of the amino acid were examined briefly.