KEGG ORTHOLOGY: K19889

ORTHOLOGY: K19889

Entry

K19889            Tight     KO

Symbol

rebM

Name

demethylrebeccamycin-D-glucose O-methyltransferase [EC:2.1.1.164]

Pathway

map00404

Staurosporine biosynthesis

map01100

Metabolic pathways

map01110

Biosynthesis of secondary metabolites

Module

M00789

Rebeccamycin biosynthesis, tryptophan => rebeccamycin

Reaction

R09569

S-adenosyl-L-methionine:demethylrebeccamycin-D-glucose O-methyltransferase

Brite

KEGG Orthology (KO) [BR:ko00001]
09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00404 Staurosporine biosynthesis
    K19889  rebM; demethylrebeccamycin-D-glucose O-methyltransferase
Enzymes [BR:ko01000]
2. Transferases
  2.1  Transferring one-carbon groups
   2.1.1  Methyltransferases
    2.1.1.164  demethylrebeccamycin-D-glucose O-methyltransferase
     K19889  rebM; demethylrebeccamycin-D-glucose O-methyltransferase

Genes

AG:	BAC10678(rebM)

Reference

PMID:18502766

Authors

Singh S, McCoy JG, Zhang C, Bingman CA, Phillips GN Jr, Thorson JS

Title

Structure and mechanism of the rebeccamycin sugar 4'-O-methyltransferase RebM.

Journal

J Biol Chem 283:22628-36 (2008)
DOI:10.1074/jbc.M800503200

Sequence

[ag:BAC10678]

LinkDB

ENZYME: 2.1.1.164

Entry

EC 2.1.1.164                Enzyme

Name

demethylrebeccamycin-D-glucose O-methyltransferase;
RebM

Class

Transferases;
Transferring one-carbon groups;
Methyltransferases

Sysname

S-adenosyl-L-methionine:demethylrebeccamycin-D-glucose O-methyltransferase

Reaction(IUBMB)

4'-demethylrebeccamycin + S-adenosyl-L-methionine = rebeccamycin + S-adenosyl-L-homocysteine [RN:R09569]

Reaction(KEGG)

R09569

Substrate

4'-demethylrebeccamycin;
S-adenosyl-L-methionine [CPD:C00019]

Product

rebeccamycin [CPD:C19701];
S-adenosyl-L-homocysteine [CPD:C00021]

Comment

Catalyses the last step in the biosynthesis of rebeccamycin, an indolocarbazole alkaloid produced by the bacterium Lechevalieria aerocolonigenes. The enzyme is able to use a wide variety substrates, tolerating variation on the imide heterocycle, deoxygenation of the sugar moiety, and even indolocarbazole glycoside anomers [1]. The enzyme is a member of the general acid/base-dependent O-methyltransferase family [2].

History

EC 2.1.1.164 created 2010

Pathway

ec00404

Staurosporine biosynthesis

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K19889

demethylrebeccamycin-D-glucose O-methyltransferase

Reference

1 [PMID:16575939]

Authors

Zhang C, Albermann C, Fu X, Peters NR, Chisholm JD, Zhang G, Gilbert EJ, Wang PG, Van Vranken DL, Thorson JS

Title

RebG- and RebM-catalyzed indolocarbazole diversification.

Journal

Chembiochem 7:795-804 (2006)
DOI:10.1002/cbic.200500504

Sequence

[ag:BAC10678]

Reference

2 [PMID:18502766]

Authors

Singh S, McCoy JG, Zhang C, Bingman CA, Phillips GN Jr, Thorson JS

Title

Structure and mechanism of the rebeccamycin sugar 4'-O-methyltransferase RebM.

Journal

J Biol Chem 283:22628-36 (2008)
DOI:10.1074/jbc.M800503200

Sequence

[ag:BAC10678]

Other DBs

ExplorEnz - The Enzyme Database:

2.1.1.164

IUBMB Enzyme Nomenclature:

2.1.1.164

ExPASy - ENZYME nomenclature database:

2.1.1.164

BRENDA, the Enzyme Database:

2.1.1.164

LinkDB

REACTION: R09569

Entry

R09569                      Reaction

Name

S-adenosyl-L-methionine:demethylrebeccamycin-D-glucose O-methyltransferase

Definition

4'-O-Demethylrebeccamycin + S-Adenosyl-L-methionine <=> Rebeccamycin + S-Adenosyl-L-homocysteine

Equation

C19700 + C00019 <=> C19701 + C00021

Reaction class

RC00003

C00019_C00021

RC00466

C19700_C19701

Enzyme

2.1.1.164

Pathway

rn00404

Staurosporine biosynthesis

rn01100

Metabolic pathways

rn01110

Biosynthesis of secondary metabolites

Module

M00789

Rebeccamycin biosynthesis, tryptophan => rebeccamycin

Brite

Enzymatic reactions [BR:br08201]
2. Transferase reactions
  2.1  Transferring one-carbon groups
   2.1.1  Methyltransferases
    2.1.1.164
     R09569  4'-O-Demethylrebeccamycin + S-Adenosyl-L-methionine <=> Rebeccamycin + S-Adenosyl-L-homocysteine

Orthology

K19889

demethylrebeccamycin-D-glucose O-methyltransferase [EC:2.1.1.164]

Other DBs

RHEA:

27356

LinkDB

DBGET integrated database retrieval system