ENZYME-CATALYZED OXIDATION OF NAZLININ AND NAZLININ DERIVATIVES - CHARACTERIZATION OF THE REACTION-PRODUCTS

Porcine Kidney Diamine Oxidase (PKDO) was used to catalyse the oxidati ve transformation of Nitraria alkaloids. Nazlinin yielded indoloquinol izidine 4, an alkaloid which has been obtained as a natural product fr om Nitraria plant extracts. Oxidative deamination of 1-(4-butylamino)- beta-carboline 10 with PKDO yielded an unstable aldehyde (11), which c yclised to a new, arborescidine-type azepine (12). Addition of alcohol dehydrogenase during the oxidative deamination reduced the aldehyde i n situ to the corresponding alcohol 13. Topaquinone-analogue 9 was eff ective as a stoichiometric oxidant for these primary amines. Character isation of the enzyme reaction products was done by comparison with th e chemically synthesised compounds. Copyright (C) 1996 Elsevier Scienc e Ltd