The popular Chinese vegetable Toona sinensis was found to contain (S,S)-?-glutamyl-(cis-S-1-propenyl)thioglycine and its trans- analogue. The planar structures of these novel norcysteine-containing compounds were elucidated by mass spectrometry and nuclear magnetic resonance. The absolute configuration of the derivatized cis- isomer was determined by comparison of experimental with computed vibrational circular dichroism data. Serendipitously, the (S,S)-?-glutamyl-(cis-S-1-propenyl)thioglycine derivative crystallized, permitting confirmation of the absolute configuration by X-ray crystallography.

Structure elucidation of novel nor-cysteine-containing dipeptides from the Chinese vegetable <i>Toona sinensis</i>

248th National Meeting (2014)

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Structure elucidation of novel nor-cysteine-containing dipeptides from the Chinese vegetable Toona sinensis