CYP719B1 is salutaridine synthase, the C-C phenol-coupling enzyme of morphine biosynthesis in opium poppy. The Journal of biological chemistry [J Biol Chem] Journal article | | Title | CYP719B1 is salutaridine synthase, the C-C phenol-coupling enzyme of morphine biosynthesis in opium poppy. | | Author(s) | Gesell A, Rolf M, Ziegler J, Díaz Chávez ML, Huang FC, Kutchan TM | | Institution | Leibniz-Institut für Pflanzenbiochemie, D-06120 Halle (Saale), Germany. | | Source | J Biol Chem 2009 Sep 4; 284(36):24432-42. | | MeSH | Amino Acid Sequence
Animals
Catalysis
Cell Line
Cytochrome P-450 Enzyme System
Gene Expression
Molecular Sequence Data
Morphinans
Morphine
Papaver
Plant Proteins
Recombinant Proteins
Spodoptera
| | Abstract | Morphine is a powerful analgesic natural product produced by the opium poppy Papaver somniferum. Although formal syntheses of this alkaloid have been reported, the morphine molecule contains five stereocenters and a C-C phenol linkage that to date render a total synthesis of morphine commercially unfeasible. The C-C phenol-coupling reaction along the biosynthetic pathway to morphine in opium poppy is catalyzed by the cytochrome P450-dependent oxygenase salutaridine synthase. We report herein on the identification of salutaridine synthase as a member of the CYP719 family of cytochromes P450 during a screen of recombinant cytochromes P450 of opium poppy functionally expressed in Spodoptera frugiperda Sf9 cells. Recombinant CYP719B1 is a highly stereo- and regioselective enzyme; of forty-one compounds tested as potential substrates, only (R)-reticuline and (R)-norreticuline resulted in formation of a product (salutaridine and norsalutaridine, respectively). To date, CYP719s have been characterized catalyzing only the formation of a methylenedioxy bridge in berberine biosynthesis (canadine synthase, CYP719A1) and in benzo[c]phenanthridine biosynthesis (stylopine synthase, CYP719A14). Previously identified phenol-coupling enzymes of plant alkaloid biosynthesis belong only to the CYP80 family of cytochromes. CYP719B1 therefore is the prototype for a new family of plant cytochromes P450 that catalyze formation of a phenol-couple. | | Language | eng | | Pub Type(s) | Journal Article
Research Support, Non-U.S. Gov't
| | PubMed ID | 19567876 |
|
|
| |
Advertise on this site.
| | |
|
