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Neopinone isomerase is involved in codeine and morphine biosynthesis in opium poppy

by Ramasamy, Sukanya , Yeaman, Sam , Dastmalchi, Mehran , Chang, Limei , Chen, Rongji , Facchini, Peter J. , Hagel, Jillian M. , Chen, Xue

in 631/553/318 / 631/92/349 / 631/92/60 / 631/92/607 / Alkaloids / Biochemical Engineering / Biochemistry / Bioorganic Chemistry / Biosynthesis / Catalysis / Cell Biology / Chemistry / Chemistry and Materials Science / Chemistry/Food Science / Codeine / Codeine - biosynthesis / Hydrocodone - analogs & derivatives / Hydrocodone - metabolism / Isomerases - physiology / Isomerization / Isomers / Morphine / Morphine - biosynthesis / Narcotics / Opioids / Opium - metabolism / Papaver - enzymology / Papaver - metabolism / Papaver somniferum / Pathogenesis / Proteins / Thebaine - metabolism / Yeast

2019

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Neopinone isomerase is involved in codeine and morphine biosynthesis in opium poppy

by Ramasamy, Sukanya , Yeaman, Sam , Dastmalchi, Mehran , Chang, Limei , Chen, Rongji , Facchini, Peter J. , Hagel, Jillian M. , Chen, Xue

2019

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Neopinone isomerase is involved in codeine and morphine biosynthesis in opium poppy

by Ramasamy, Sukanya , Yeaman, Sam , Dastmalchi, Mehran , Chang, Limei , Chen, Rongji , Facchini, Peter J. , Hagel, Jillian M. , Chen, Xue

2019

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Journal Article

Neopinone isomerase is involved in codeine and morphine biosynthesis in opium poppy

Ramasamy, Sukanya,

Yeaman, Sam,

Dastmalchi, Mehran,

Chang, Limei,

Chen, Rongji,

Facchini, Peter J.,

Hagel, Jillian M.,

Chen, Xue

2019

Overview

The isomerization of neopinone to codeinone is a critical step in the biosynthesis of opiate alkaloids in opium poppy. Previously assumed to be spontaneous, the process is in fact catalyzed enzymatically by neopinone isomerase (NISO). Without NISO the primary metabolic products in the plant, in engineered microbes and in vitro are neopine and neomorphine, which are structural isomers of codeine and morphine, respectively. Inclusion of NISO in yeast strains engineered to convert thebaine to natural or semisynthetic opiates dramatically enhances formation of the desired products at the expense of neopine and neomorphine accumulation. Along with thebaine synthase, NISO is the second member of the pathogenesis-related 10 (PR10) protein family recently implicated in the enzymatic catalysis of a presumed spontaneous conversion in morphine biosynthesis. Neopinone isomerase catalyzes the isomerization of the opiate alkaloid neopinone to codeinone, driving the biosynthesis of codeine and morphine and preventing accumulation of their isomers neopine and neomorphine.

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Publisher

Nature Publishing Group US,Nature Publishing Group

Subject

/ Biochemical Engineering

/ Biochemistry