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Information on EC 4.3.3.5 - 4'-demethylrebeccamycin synthase and Organism(s) Lentzea aerocolonigenes and UniProt Accession Q8KHE4

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EC Tree
     4 Lyases
         4.3 Carbon-nitrogen lyases
             4.3.3 Amine-lyases
                4.3.3.5 4'-demethylrebeccamycin synthase
IUBMB Comments
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].
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This record set is specific for:
Lentzea aerocolonigenes
UNIPROT: Q8KHE4
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The taxonomic range for the selected organisms is: Lentzea aerocolonigenes
The enzyme appears in selected viruses and cellular organisms
Synonyms
ngt, RebG, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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].
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
6-N-methylarcyriaflavin C + beta-D-glucose
13-(beta-D-glucosyl)-6-N-methylarcyriaflavin C
show the reaction diagram
i.e. 12,13-dihydro-2,10-dihydroxy-5H-indolo-[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione, an indolocarbazole produced by Arcyria denudata
-
-
?
J-109303 + beta-D-glucose
J-109384 + H2O
show the reaction diagram
-
-
-
?
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
-
80.4% conversion rate
major product is N-glycosylated in position 12, minor product in position 13, ratio of products is 3:1
-
?
carbazole + beta-D-glucose
N-(beta-D-glucosyl)-carbazole + H2O
show the reaction diagram
-
poor substrate
-
-
?
indolo-[2,3-a]-carbazole + beta-D-glucose
N-(beta-D-glucosyl)-indolo-[2,3-a]-carbazole + H2O
show the reaction diagram
-
70.3% conversion rate
-
-
?
rebeccamycin aglycone + beta-D-glucose
rebeccamycin + H2O
show the reaction diagram
-
-
-
-
?
staurosporine aglycone + beta-D-glucose
N-(beta-D-glucosyl)-staurosporine aglycone + H2O
show the reaction diagram
-
96.4% conversion rate
major product is N-glycosylated in position 12, minor product in position 13, ratio of products is 2:1
-
?
additional information
?
-
-
remarkable lack of RebG regioselectivity in the presence of asymmetric substrates
-
-
?
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
-
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
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
REBG_LENAE
421
0
46021
Swiss-Prot
-
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
functional expression in Streptomyces mobaraensis
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant enzyme. from inclusion bodies
-
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Streptomyces lividans and Escherichia coli
-
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Zhang, C.; Albermann, C.; Fu, X.; Peters, N.R.; Chisholm, J.D.; Zhang, G.; Gilbert, E.J.; Wang, P.G.; van Vranken, D.L.; Thorson, J.S.
RebG- and RebM-catalyzed indolocarbazole diversification
Chembiochem
7
795-804
2006
Lentzea aerocolonigenes
Manually annotated by BRENDA team
Onaka, H.; Taniguchi, S.; Igarashi, Y.; Furumai, T.
Characterization of the biosynthetic gene cluster of rebeccamycin from Lechevalieria aerocolonigenes ATCC 39243
Biosci. Biotechnol. Biochem.
67
127-138
2003
Lentzea aerocolonigenes
Manually annotated by BRENDA team
Ohuchi, T.; Ikeda-Araki, A.; Watanabe-Sakamoto, A.; Kojiri, K.; Nagashima, M.; Okanishi, M.; Suda, H.
Cloning and expression of a gene encoding N-glycosyltransferase (ngt) from Saccarothrix aerocolonigenes ATCC39243
J. Antibiot.
53
393-403
2000
Lentzea aerocolonigenes (Q8KHE4), Lentzea aerocolonigenes ATCC 39243 (Q8KHE4)
Manually annotated by BRENDA team