KEGG   ENZYME: 2.1.1.122
Entry
EC 2.1.1.122                Enzyme                                 
Name
(S)-tetrahydroprotoberberine N-methyltransferase;
tetrahydroprotoberberine cis-N-methyltransferase
Class
Transferases;
Transferring one-carbon groups;
Methyltransferases
Sysname
S-adenosyl-L-methionine:(S)-7,8,13,14-tetrahydroprotoberberine cis-N-methyltransferase
Reaction(IUBMB)
S-adenosyl-L-methionine + an (S)-7,8,13,14-tetrahydroprotoberberine = S-adenosyl-L-homocysteine + an (S)-cis-N-methyl-7,8,13,14-tetrahydroprotoberberine [RN:R04716]
Reaction(KEGG)
R04716 > R04691 R08789
Substrate
S-adenosyl-L-methionine [CPD:C00019];
(S)-7,8,13,14-tetrahydroprotoberberine [CPD:C22684]
Product
S-adenosyl-L-homocysteine [CPD:C00021];
(S)-cis-N-methyl-7,8,13,14-tetrahydroprotoberberine [CPD:C05318]
Comment
Involved in the biosynthesis of isoquinoline alkaloids in plants. Substrates include (S)-canadine, (S)-stylopine, and (S)-tetrahydropalmatine.
History
EC 2.1.1.122 created 1999, modified 2023
Pathway
ec00950  Isoquinoline alkaloid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K13396  (S)-tetrahydroprotoberberine N-methyltransferase
Genes
PSOM113295244 113317972 113320885 113323066
Reference
1
  Authors
Rueffer M, Zumstein G, Zenk MH.
  Title
Partial purification and characterization of S-adenosyl-L-methionine:(S)-tetrahydroprotoberberine cis-N-methyltransferase from suspension-cultured cells of Eschscholtzia and Corydalis.
  Journal
Phytochemistry 29:3727-3733 (1990)
Reference
2  [PMID:17389594]
  Authors
Liscombe DK, Facchini PJ
  Title
Molecular cloning and characterization of tetrahydroprotoberberine cis-N-methyltransferase, an enzyme involved in alkaloid biosynthesis in opium poppy.
  Journal
J Biol Chem 282:14741-51 (2007)
DOI:10.1074/jbc.M611908200
  Sequence
Reference
3  [PMID:19624470]
  Authors
Liscombe DK, Ziegler J, Schmidt J, Ammer C, Facchini PJ
  Title
Targeted metabolite and transcript profiling for elucidating enzyme function: isolation of novel N-methyltransferases from three benzylisoquinoline alkaloid-producing species.
  Journal
Plant J 60:729-43 (2009)
DOI:10.1111/j.1365-313X.2009.03980.x
Other DBs
ExplorEnz - The Enzyme Database: 2.1.1.122
IUBMB Enzyme Nomenclature: 2.1.1.122
ExPASy - ENZYME nomenclature database: 2.1.1.122
BRENDA, the Enzyme Database: 2.1.1.122
CAS: 106878-42-6
LinkDB

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