CYANOGENESIS IN MANIOC - CONCERNING LOTAUSTRALIN

A glucoside of 2-hydroxy-2-methylbutyronitrile was shown to be present, in low concentration compared with linamarin, in three samples of relatively bitter tubers of manioc (Manihot esculenta Crantz). The glucoside was separated, as the trimethylsilyl derivative, by gas chromatography and identified by mass spectrometry. The β-d-glucopyranosides of the enantiomeric hydroxy nitriles were synthesized from acetobromoglucose and methyl ethyl ketone cyanohydrin, being separated by chromatography of the acetates. The less levorotatory of the synthetic glucosides, having the (R) configuration at the asymmetric center of the aglucone, was shown to be identical with the compound which occurs naturally in white clover (lotaustralin). © 1969.