Enzymatic formation of protopines by a microsomal cytochrome P-450 system of Corydalis vaginans

@article{Rueffer1987EnzymaticFO,
  title={Enzymatic formation of protopines by a microsomal cytochrome P-450 system of Corydalis vaginans},
  author={M. Rueffer and M. Zenk},
  journal={Tetrahedron Letters},
  year={1987},
  volume={28},
  pages={5307-5310}
}
Abstract A microsomal cytochrome P-450-NADPH dependent enzyme which hydroxylates stereo- and regiospecifically carbon atom 14 of (S)- cis -N- methyltetrahydroprotoberberines has been discovered in a number of plant cell cultures originating from species containing protopine alkaloids; the monooxygenase was solubilized, partially purified (100-fold) and characterized. 
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References

SHOWING 1-10 OF 14 REFERENCES
S-adenosyl-l-methionine: (S) -7,8,13, 14-tetrahydroberberine--n-methyltransferase, a branch point enzyme in the biosynthesis of benzophenanthridine and protopine alkaloids.
The enzyme which transfers the CH3-group of S-adenosylmethionine to the nitrogen atom of (S)-tetrahydroberberine and (S)-stylopine is found to occur in a number of plant cell cultures originatingExpand
Partial Purification and Properties of (S)-Norlaudanosoline Synthase from Eschscholtzia tenuifolia Cell Cultures.
TLDR
By means of isoelectric focusing and disc-gel electrophoresis evidence was obtained for the existence of four norlaudanosoline synthase isoenzymes, none of which catalyses the reaction of dopamine with 3,4-dihydroxyphenylpyruvate, the key intermediate in the formation of isoquinoline alkaloids occurring in the plant kingdom. Expand
Biosynthesis of Benzo[c]phenanthridine Alkaloids Sanguinarine, Chelirubine and Macarpine
The biosynthesis of the benzo[c]phenanthridine alkaloids was investigated in a cell suspension culture of Macleaya cordata (papaveraceae). Feeding experiments define the biosynthetic pathwayExpand
Zur Biosynthese der Alkaloide vom Rhoeadin‐Typ
TLDR
It was shown, using Papaver bracteatum plants, that [N-14CH3, 8-14C]dl-tetrahydropalmatine methiodide (Ia) is incorporated with high efficiency into alpinigenine (III), and apparently the incorporation of the N-quaternary salt is a specific one. Expand
Biosynthesis of alpinigenine by way of tetrahydroprotoberberine and protopine intermediates
Abstract In the biosynthesis of the benzazepine alkaloid alpinigenine a N -methylation step followed by hydroxylation α to nitrogen has now been shown more conclusively to be involved in theExpand
Rapid isolation of a plant microsomal fraction by Mg2+ — precipitation
TLDR
A procedure for the rapid preparation of a plant microsomal fraction by Mg2+-precipitation was developed and will be described in this communication. Expand
Tetrahedron Letters
A new strategy for the synthesis of (+)-vernolepin (1), (+)-vernodalin (2), and (+)-8-deoxyvernolepin (3), from the accessible germacrolides (+)-salonitenolide (4) and (+)-costunolide (5), has beenExpand
and K
  • Tagahara. Chem.Pharm.Bull. 22, 2457 (1974). (Received in Germany 24 July
  • 1987
Helv.Chim.Acta
  • Helv.Chim.Acta
  • 1983
J.Chem.Soc. Perkin I
  • J.Chem.Soc. Perkin I
  • 1975
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