KEGG ORTHOLOGY: K13396

ORTHOLOGY: K13396

Entry

K13396                      KO

Symbol

E2.1.1.122

Name

(S)-tetrahydroprotoberberine N-methyltransferase [EC:2.1.1.122]

Pathway

map00950

Isoquinoline alkaloid biosynthesis

map01100

Metabolic pathways

map01110

Biosynthesis of secondary metabolites

Module

M00945

Sanguinarine biosynthesis, (S)-reticuline => sanguinarine

M00946

Noscapine biosynthesis, (S)-reticuline => noscapine

Reaction

R04691

R08789

S-adenosyl-L-methionine:(S)-canadine N-methyltransferase

Brite

KEGG Orthology (KO) [BR:ko00001]
09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00950 Isoquinoline alkaloid biosynthesis
    K13396  E2.1.1.122; (S)-tetrahydroprotoberberine N-methyltransferase
Enzymes [BR:ko01000]
2. Transferases
  2.1  Transferring one-carbon groups
   2.1.1  Methyltransferases
    2.1.1.122  (S)-tetrahydroprotoberberine N-methyltransferase
     K13396  E2.1.1.122; (S)-tetrahydroprotoberberine N-methyltransferase

Other DBs

GO:

0030782

Genes

PSOM:

113295244 113317972 113320885 113323066

AG:

AAY79177

Reference

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

[ag:AAY79177]

LinkDB

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

PSOM:

113295244 113317972 113320885 113323066

Reference

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

[ag:AAY79177]

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

REACTION: R08789

Entry

R08789                      Reaction

Name

S-adenosyl-L-methionine:(S)-canadine N-methyltransferase

Definition

S-Adenosyl-L-methionine + (S)-Canadine <=> S-Adenosyl-L-homocysteine + (S)-cis-N-Methylcanadine

Equation

C00019 + C03329 <=> C00021 + C02915

Reaction class

RC00003

C00019_C00021

RC01197

C02915_C03329

Enzyme

2.1.1.122

Pathway

rn00950

Isoquinoline alkaloid biosynthesis

rn01100

Metabolic pathways

rn01110

Biosynthesis of secondary metabolites

Module

M00946

Noscapine biosynthesis, (S)-reticuline => noscapine

Brite

Enzymatic reactions [BR:br08201]
2. Transferase reactions
  2.1  Transferring one-carbon groups
   2.1.1  Methyltransferases
    2.1.1.122
     R08789  S-Adenosyl-L-methionine + (S)-Canadine <=> S-Adenosyl-L-homocysteine + (S)-cis-N-Methylcanadine
IUBMB reaction hierarchy [BR:br08202]
2. Transferase reactions
  2.1.1.122
   R04716  (S)-Tetrahydroprotoberberine <=> (S)-cis-N-Methyl-7,8,13,14-tetrahydroprotoberberine
    R08789  (S)-Canadine <=> (S)-cis-N-Methylcanadine

Orthology

K13396

(S)-tetrahydroprotoberberine N-methyltransferase [EC:2.1.1.122]

Other DBs

RHEA:

12808

LinkDB

DBGET integrated database retrieval system