title: Oximes, nitriles and 2-hydroxynitriles as precursors in the biosynthesis of cyanogenic glucosides.
abstract: The biosynthesis of the cyanogenic glucosides, linamarin and prunasin, was investigated in linen-flax, peach and cherry-laurel shoots. It was shown that related 2-oximino acids, aldoximes, nitriles and 2-hydroxynitriles were generally good precursors of the aglycone moiety. Studies with double-labelled compounds confirmed the retention of the oximino nitrogen atom from 2-oximinoisovaleric acid and isobutyraldoxime in the biosynthesis of linamarin. A general pathway from amino acids to cyanogenic glucosides involving N-hydroxyamino acids, aldoximes, nitriles and 2-hydroxynitriles is proposed.
mesh_terms: D000447:Aldehydes / Q000378:metabolism; D000577:Amides / Q000378:metabolism; D002247:Carbon Isotopes; D002854:Chromatography, Paper; D002855:Chromatography, Thin Layer; D003486:Cyanides / Q000378:metabolism; D006027:Glycosides / Q000096:biosynthesis*; D009570:Nitriles / Q000378:metabolism*; D009587:Nitrogen Isotopes; D010091:Oximes / Q000378:metabolism*; D010944:Plants / Q000378:metabolism*; D014633:Valine / Q000378:metabolism
chemical_list: D000447:Aldehydes; D000577:Amides; D002247:Carbon Isotopes; D003486:Cyanides; D006027:Glycosides; D009570:Nitriles; D009587:Nitrogen Isotopes; D010091:Oximes; D014633:Valine