Transformations of codeine to important semisynthetic opiate derivatives byPseudomonas putidam10

Abstract

A biotransformation mixture which contained codeine and washed cells of Pseudomonas putida M10 gave rise to a number of transformation products that are of clinical importance which included hydrocodone, dihydrocodeine and 14beta-hydroxycodeine. Incubations with the same organism and codeinone gave rise to 14beta-hydroxycodeinone and 14beta-hydroxycodeine. Cell-free extracts and membrane fractions of P. putida M10 were shown to catalyse the 14beta-hydroxylation of codeinone. In addition, the potent analgesic oxycodone was shown to be produced from 14beta-hydroxycodeinone.

Combinatorial approach to the selection of active microorganisms in biotransformation: Application to sinomenine

“…Two-steps biotransformation of morphine by Cylindrocarpon didynum [25] gave the 10-␣-S-monohydroxy-2,2 -bimorphine and 10,10 -␣,␣ -S,S -dihydroxy-2,2 -bimorphine. 14-Hydroxylation of codeine was reported to take place in presence of Pseudomonas putida [26]. Other reactions such as oxidations of the alcohol in dihydromorphine and reduction of carbon-carbon double bond in morphine by P. putida [27] and, O-and N-demethylation of thebaine derivatives by Cunninghamella echinulata [28,29] were also reported.…”

Inverted binding due to a minor structural change in berberine enhances its phospholipase A2 inhibitory effect

“…This bioconversion is industrially important as it increases the analgesic potency of codeine [23]. This demethylation reaction is difficult to achieve chemically, due to the unreactive nature of tertiary carbon.…”

Biotransformation of codeine to 14-OH-codeine derivatives by Rhizobium radiobacter R89-1

“…Alkaloid biotransformation by alga Nostoc muscorum has been recently reported [21]. In all cases, biotransformations were catalyzed by morphine dehydrogenase and morphinone reductase [22][23][24][25] at rather low concentration of a substrate. No conversion was reported at concentrations of substrates exceeding 2 g/L although the reaction mixture was analyzed after 5-10 days of conversion.…”