Abstract
Porcine Kidney Diamine Oxidase (PKDO) was used to catalyse the oxidative transformation of Nitraria alkaloids. Nazlinin yielded indoloquinolizidine 4, an alkaloid which has been obtained as a natural product from Nitraria plant extracts. Oxidative deamination of 1-(4-butylamino)-β-carboline 10 with PKDO yielded an unstable aldehyde ( 11), which cyclised to a new, arborescidine-type azepine ( 12). Addition of alcohol dehydrogenase during the oxidative deamination reduced the aldehyde in situ to the corresponding alcohol 13. Topaquinone-analogue 9 was effective as a stoichiometric oxidant for these primary amines. Characterisation of the enzyme reaction products was done by comparison with the chemically synthesised compounds.
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