Partial purification and properties of S-adenosyl-l-methionine: (S)-tetrahydroprotoberberinecis-N-methyltransferase from suspension-cultured cells of Eschscholtzia and Corydalis

@article{Rueffer1990PartialPA,
  title={Partial purification and properties of S-adenosyl-l-methionine: (S)-tetrahydroprotoberberinecis-N-methyltransferase from suspension-cultured cells of Eschscholtzia and Corydalis},
  author={Martina Rueffer and Gitta Zumstein and Meinhart H. Zenk},
  journal={Phytochemistry},
  year={1990},
  volume={29},
  pages={3727-3733}
}
Abstract An enzyme has been found in different species of isoquinoline alkaloid-producing plant cell cultures which specifically N -methylates certain ( S )-tetrahydroprotoberberine alkaloids such as ( S )-canadine and ( S )-stylopine at the expense of S -adenosyl- l -methionine (SAM). It was partially purified (90-fold from Eschscholtzia californica cell suspension cultures and characterized. The enzyme has a pH optimum of 8.9, a temperature optimum at 40° and a M r of about 78 000 ± 10%. The… Expand
Purification and properties of 1-hydroxycanthin-6-one: S-adenosyl-l-methionine methyltransferase from Ailanthus altissima cell cultures
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Partial Purification and Characterization of S-Adenosyl-L- Methionine:Anthranilic Acid N-Methyltransferase from Ruta Cell Suspension Cultures
TLDR
The properties, the substrate specificity and the Michaelis-Menten constants of the purified enzyme were determined and it was found that the anthranilic acid specific N-methyltransferase is strongly inhibited by S-adenosyl-L-homocysteine. Expand
Molecular Cloning and Characterization of Tetrahydroprotoberberine cis-N-Methyltransferase, an Enzyme Involved in Alkaloid Biosynthesis in Opium Poppy*
S-Adenosyl-l-methionine:tetrahydroprotoberberine cis-N-methyltransferase (EC 2.1.1.122) catalyzes the conversion of (S)-stylopine to the quaternary ammonium alkaloid, (S)-cis-N-methylstylopine, as aExpand
Structure–function studies of tetrahydroprotoberberine N-methyltransferase reveal the molecular basis of stereoselective substrate recognition
TLDR
The insights into substrate recognition and catalysis provided here form a sound basis for the rational engineering of NMT enzymes for chemoenzymatic synthesis and metabolic engineering. Expand
Isolation and Characterization of Reticuline N-Methyltransferase Involved in Biosynthesis of the Aporphine Alkaloid Magnoflorine in Opium Poppy*
TLDR
The isolation and characterization of a phylogenetically related yet functionally distinct N-methyltransferase (NMT) from opium poppy that primarily accepts 1-benzylisoquinoline and aporphine substrates possessing a tertiary amine is reported. Expand
Difference between Enzymatic and Chemical N-methylations of Protoberberine-Type Alkaloid, Dependent on the Stereoisomer of (-)-N-methyl-7,8,13,13a-tetrahydroberberinium Salt.
A possible relation between the stereostructure of (−)-(13aS)-tetrahydroberberine (1) and its enzymatic/chemical N-methylation, an important biosynthetic reaction to isoquinoline alkaloids in plants,Expand
Developmental and inducible accumulation of gene transcripts involved in alkaloid biosynthesis in opium poppy.
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Enzymic 12-hydroxylation and 12-O-methylation of dihydrochelirubine in dihydromacarpine formation by Thalictrum bulgaricum
TLDR
This discovery leads to the complete sequence of macarpine biosynthesis which has thus far been the longest secondary product pathway completely clarified at the enzymic level. Expand
Chapter 5 The Biotransformation of Protoberberine Alkaloids by Plant Tissue Cultures
TLDR
The biochemical processes in the conversion of the protoberberines into the benzophenanthridines occur similarly in intact plants and callus tissues. Expand
Heterologous expression of alkaloid biosynthetic genes--a review.
TLDR
The biosynthesis at the enzyme level of at-least two tetrahydrobenzylisoquinoline alkaloids, the benzophenanthridine alkaloid sanguinarine in the California poppy, Eschscholtzia californica, and the bisbenzymunine in barberry, Berberis stolonifera, has been elucidated in detail. Expand
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