O- Demethylation

Hunnemannine, CigHiB0N(0H)(0Me)(CH202). (Item 49 list, p. 173.) M.p. 209°. Diazomethane converts the base into a-oZZocryptopine, m.p. 159-60°, so that hunnemannine appears to be O-demethyl-a-oZZocrypto-pine. The ethyl ether has m.p. 168° and on degradation by the method... [Pg.302]

Smith RV, Erhardt PW, Leslie SW. Microsomal O-demethylation, A-demethyl-ation and aromatic hydroxylation in the presence of bisulfite and dithiothreitol. Res Commun Chem Path Pharmacol 1975 12 181-4. [Pg.464]

Grbic-Galic D (1986) O-Demethylation, dehydroxylation, ring-reduction and cleavage of aromatic substrates by Enterobacteriaceae under anaerobic conditions. J Appl Bacteriol 61 491-497. [Pg.82]

Resistance of house flies (Musca domestica) to DDT was attributed to its transformation to the nontoxic DDE, and the enzyme that carries the dehydrochlorination has been characterized in DDT-resistant flies (Lipke and Kearns 1959a,b). The herbicide alachlor is transformed by chironomid larvae by O-demethylation followed by loss of the chloroacetyl group to produce 2,6-diethylaniline... [Pg.96]

Abe T, E Masai, K Miyauchi, Y Katayama, M Fukuda (2005) A tetrahydrofolate-dependent O-demethyl-ase, LigM, is crucial for catabolism of vanillate and syringate in Sphingomonas paucimobilis SYK-6. J Bacterial 187 2030-2037. [Pg.581]

Berman MH, AC Frazer (1992) Importance of tetrahydrofolate and ATP in the anaerobic O-demethylation reaction for phenylmethylethers. Appl Environ Microbiol 58 925-931. [Pg.581]

Sakano, K. Inagaki, Y. Oikawa, S. Hiraku, Y. Kawanishi, S. Copper-mediated oxidative DNA damage induced by eugenol possible involvement of O-demethylation. Mutat. Res. 2004, 565, 35 44. [Pg.354]

Regioselective 9-O-demethylation of 15 was achieved by pyrolysis at 190°C to give berberrubine (71) (Scheme 17) (55), and 64 was similarly converted to palmatrubine (72), which was derivatized to [9-0-methyl-14C] palmatine for biosynthetic studies (59). [Pg.154]

Nonresponse to codeine (PMs of CYP2D6 fail to O-demethylate to morphine)... [Pg.155]

It has been suggested that compounds with 2,5-dimethoxy substituents may be O-demethylated to generate reactive quinone species, and that this may play a role in their high activity (193,197,205). However, this substitution also leads to high-energy molecular orbitals. Furthermore, transposing the 4-methyl of... [Pg.179]

Microbial transformations of ellipticine (15) and 9-methoxyellipticine (16) were reported by Chien and Rosazza (143, 144). Of 211 cultures screened for their abilities to transform 9-methoxyellipticine (16), several, including Botrytis alii (NRRL 2502), Cunninghamella echinulata (NRRL 1386), C. echinulata (NRRL 3655), and Penicillium brevi-compactum (ATCC 10418), achieved O-demethylation of 16 in good yield (Scheme 9). P. brevi-compactum was used to prepare 9-hydroxyellipticine (22) from the methoxylated precursor, and 150 mg of product was obtained from 400 mg of starting material (37% yield). The structure of the metabolite was confirmed by direct comparison with authentic 9-hydroxyellipticine (143). O-Demethylation is a common microbial metabolic transformation with 16 and many other alkaloids (143). Meunier et al. have also demonstrated that peroxidases catalyze the O-demethylation reaction with 9-methoxyellipticine (145). [Pg.359]

These transformation reactions are similar in part to those previously observed for laudanosine (201) and for the aporphine-benzylisoquinoline alkaloid thalicarpine (202). Laudanosine underwent regiospecific O-demethylation at... [Pg.385]

Biotransformations of morphinan alkaloids have been reported for plant, fungal, and mammalian enzymatic systems with emphasis on rather specific reactions such as the reduction of ketones, N- and O-demethylation, and perox-idative transformations. Furuya et al. used immobilized tissue culture cells of Papaver somniferum to accomplish the selective reduction of codeinone (135) to codeine (136) (207) (Scheme 30). Suspension cultures of a well-established cell line of P. somniferum were grown for one week as a source of cell mass for immobilization in calcium alginate. The cells continued to live in the alginate matrix for 6 months maintaining their biological activity. The reduction of co-... [Pg.389]

Ellipticine, 9-methoxy- O-Demethylation Cunninghamella (2), Penicillium, Botrytis. 143... [Pg.405]

Vindoline, 14,15-dihydro- Imine formation, carbinolamine, O-demethylation Streptomyces 178... [Pg.407]

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