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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].
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3-bromo-indolo-[2,3-a]-carbazole + beta-D-glucose
N-(beta-D-glucosyl)-3-bromo-indolo-[2,3-a]-carbazole + H2O
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Substrates: 80.4% conversion rate
Products: 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
carbazole + beta-D-glucose
N-(beta-D-glucosyl)-carbazole + H2O
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Substrates: poor substrate
Products: -
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indolo-[2,3-a]-carbazole + beta-D-glucose
N-(beta-D-glucosyl)-indolo-[2,3-a]-carbazole + H2O
-
Substrates: 70.3% conversion rate
Products: -
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J-109303 + beta-D-glucose
J-109384 + H2O
rebeccamycin aglycone + beta-D-glucose
rebeccamycin + H2O
-
Substrates: -
Products: -
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staurosporine aglycone + beta-D-glucose
N-(beta-D-glucosyl)-staurosporine aglycone + H2O
-
Substrates: 96.4% conversion rate
Products: 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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-
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Substrates: remarkable lack of RebG regioselectivity in the presence of asymmetric substrates
Products: -
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6-N-methylarcyriaflavin C + beta-D-glucose
13-(beta-D-glucosyl)-6-N-methylarcyriaflavin C
Substrates: 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
Products: -
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6-N-methylarcyriaflavin C + beta-D-glucose
13-(beta-D-glucosyl)-6-N-methylarcyriaflavin C
Substrates: 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
Products: -
?
J-109303 + beta-D-glucose
J-109384 + H2O
Substrates: -
Products: -
?
J-109303 + beta-D-glucose
J-109384 + H2O
Substrates: -
Products: -
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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
brenda
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
brenda
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)
brenda