1,2-dehydroreticuline synthase

Class of enzymes From Wikipedia, the free encyclopedia

1,2-dehydroreticuline synthase (EC 1.14.19.54) and CYP Symbol CYP82Y2 (cytochrome P450, family 82, member Y2), is an enzyme isolated from the opium poppy Papaver somniferum and the field poppy Papaver rhoeas that catalyzes the chemical reaction:[1][2][3]

 
 
O2
2 H2O
Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right
 
 
 
2D representation of the chemical structure of Q27103030.
reticulinylium cation
 

The three substrates of this enzyme are (S)-reticuline, reduced nicotinamide adenine dinucleotide phosphate (NADPH) and oxygen. Its products are 1,2-dehydroreticulinium cation, oxidised NADP+, and water. The enzyme from field poppy is specific for the (S) enantiomer of reticuline.[1] In the opium poppy, this enzyme forms a fusion protein with 1,2-dehydroreticulinium reductase (NADPH), which immediately converts the reticulinylium cation into {R)-reticuline. The overall result is that (S)-reticuline is converted to {R)-reticuline, which is the precursor of salutaridine, on the pathway to morphine.[4][5] This gene fusion event has been suggested to evolve only once, about 20 million years ago.[6][7]

 
 
 
Rightward reaction arrow
 
 
 
 
 
 
Rightward reaction arrow
 
 
 

The enzyme is a hemoprotein of cytochrome P450 type.[3][4]

References

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