Information on EC 4.3.3.5 - 4'-demethylrebeccamycin synthase

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The expected taxonomic range for this enzyme is: Lechevalieria aerocolonigenes

EC NUMBER
COMMENTARY hide
4.3.3.5
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RECOMMENDED NAME
GeneOntology No.
4'-demethylrebeccamycin synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
4'-O-demethylrebeccamycin + H2O = dichloro-arcyriaflavin A + beta-D-glucose
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of antibiotics
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rebeccamycin biosynthesis
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Staurosporine biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
4'-demethylrebeccamycin D-glucose-lyase
This enzyme catalyses a step in the biosynthesis of rebeccamycin, an indolocarbazole alkaloid produced by the bacterium Lechevalieria aerocolonigenes. The enzyme is a glycosylase, and acts in the reverse direction to that shown. It has a wide substrate range, and was shown to glycosylate several substrates, including the staurosporine aglycone, EJG-III-108A, J-104303, 6-N-methyl-arcyriaflavin C and indolo-[2,3-a]-carbazole [1,2].
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain ATCC39243
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
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enzyme is part of the biosynthetic gene cluster for synthesis of rebeccamycin in Lechevalieria aerocolonigenes ATCC 39243. Besides N-glycosyltransferase RebG, genes encode a monooxygenase RebC, methyltransferase RebM, transcriptional activator RebR, and halogenase RebH. A RebG gene disruption mutant produces the rebeccamycin aglycone but not rebeccamycin itself
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
3-bromo-indolo-[2,3-a]-carbazole + beta-D-glucose
N-(beta-D-glucosyl)-3-bromo-indolo-[2,3-a]-carbazole + H2O
show the reaction diagram
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80.4% conversion rate
major product is N-glycosylated in position 12, minor product in position 13, ratio of products is 3:1
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?
6-N-methylarcyriaflavin C + beta-D-glucose
13-(beta-D-glucosyl)-6-N-methylarcyriaflavin C
show the reaction diagram
carbazole + beta-D-glucose
N-(beta-D-glucosyl)-carbazole + H2O
show the reaction diagram
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poor substrate
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?
indolo-[2,3-a]-carbazole + beta-D-glucose
N-(beta-D-glucosyl)-indolo-[2,3-a]-carbazole + H2O
show the reaction diagram
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70.3% conversion rate
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?
J-109303 + beta-D-glucose
J-109384 + H2O
show the reaction diagram
rebeccamycin aglycone + beta-D-glucose
rebeccamycin + H2O
show the reaction diagram
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?
staurosporine aglycone + beta-D-glucose
N-(beta-D-glucosyl)-staurosporine aglycone + H2O
show the reaction diagram
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96.4% conversion rate
major product is N-glycosylated in position 12, minor product in position 13, ratio of products is 2:1
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?
additional information
?
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remarkable lack of RebG regioselectivity in the presence of asymmetric substrates
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant enzyme. from inclusion bodies
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Streptomyces lividans and Escherichia coli
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information