KEGG ENZYME: 2.1.1.122

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, M.H.

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

DBGET integrated database retrieval system