Biocatalytic Conversion of Thebaine to Codeine with High Efficiency

Thebaine
Thebaine


Thebaine is a morphine pathway biosynthesis intermediary utilized in the pharmaceutical to make oxycodone, oxymorphone, buprenorphine, and naloxone, an opiate antagonist.

Paramorphine, also known as codeine methyl enol ether, is an opiate alkaloid that gets its name from the Greek word that (Thebes), which means "Thebes." Thebaine is a minor opium ingredient that is chemically related to morphine and codeine but has stimulatory rather than depressive effects. It induces convulsions akin to strychnine poisoning at large doses. Unlike the inert natural enantiomer (-)paramorphine, the synthetic enantiomer (+) paramorphine has analgesic actions that appear to be mediated through opioid receptors. Paramorphine is the principal alkaloid derived from Papaver bracteatum (Iranian opium / Persian poppy) and may be transformed industrially into a range of chemicals, including hydrocodone, hydromorphone, oxycodone, oxymorphone, nalbuphine, naloxone, naltrexone, buprenorphine, and etorphine. Paramorphine can also be used to make butorphanol.

The Thebaine concentration of opium obtained in India's Madhya Pradesh region has been determined to be between 1.5 and 2.0 percent. In the Government Opium and Alkaloid Works, Neemuch, a technological procedure for recovering paramorphine from the mother liquor left over after the separation of natural codeine was devised in the lab and scaled up to an industrial scale. The technical specifics of a method for recovering paramorphine from waste slaked-lime residues derived from crude alkaloid cake mother liquor in the Government Opium and Alkaloid Works at Ghazipur have been worked out. Paramorphine recovery would aid in increasing codeine production, and paramorphine can also be used as a raw material in the creation of other medications. After the separation of paramorphine, cryptopine was also recovered from the mother liquor.

The final step in the production of Thebaine is catalyzed by a pathogenesis-related 10 protein. Long thought to be a spontaneous process, the final stage in the production of paramorphine, a pentacyclic opiate alkaloid easily converted to the narcotic painkillers codeine and morphine in the opium poppy. We discovered and refined a new enzyme from opium poppy latex that can efficiently synthesize paramorphine from (7S)-salutaridinol 7-O-acetate at the expense of labile hydroxylated byproducts, which are formed preferentially by spontaneous allylic elimination. Paramorphine synthase (THS), a member of the pathogenesis-related 10 protein (PR10) superfamily, is encoded inside a unique gene cluster in the opium poppy genome that also contains genes encoding the four biosynthetic enzymes upstream. THS is a vital missing component in the development of fermentation-based opiate manufacturing, and it boosts paramorphine yield in engineered yeast substantially.

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