Reaction participants Show >> << Hide
- Name help_outline 4'-demethylrebeccamycin Identifier CHEBI:595389 (Beilstein: 9461416) help_outline Charge 0 Formula C26H19Cl2N3O7 InChIKeyhelp_outline NNPBOGAWNUIKAO-RJZBGXQMSA-N SMILEShelp_outline OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)n1c2c(Cl)cccc2c2c3C(=O)NC(=O)c3c3c4cccc(Cl)c4[nH]c3c12 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H2O Identifier CHEBI:15377 (Beilstein: 3587155; CAS: 7732-18-5) help_outline Charge 0 Formula H2O InChIKeyhelp_outline XLYOFNOQVPJJNP-UHFFFAOYSA-N SMILEShelp_outline [H]O[H] 2D coordinates Mol file for the small molecule Search links Involved in 6,204 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline β-D-glucose Identifier CHEBI:15903 (Beilstein: 1281607; CAS: 492-61-5) help_outline Charge 0 Formula C6H12O6 InChIKeyhelp_outline WQZGKKKJIJFFOK-VFUOTHLCSA-N SMILEShelp_outline OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 39 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline dichloroarcyriaflavin A Identifier CHEBI:330772 (Beilstein: 4587289) help_outline Charge 0 Formula C20H9Cl2N3O2 InChIKeyhelp_outline ZGCSNRKSJLVANE-UHFFFAOYSA-N SMILEShelp_outline Clc1cccc2c1[nH]c1c3[nH]c4c(Cl)cccc4c3c3C(=O)NC(=O)c3c21 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
RHEA:27397 | RHEA:27398 | RHEA:27399 | RHEA:27400 | |
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Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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RebG- and RebM-catalyzed indolocarbazole diversification.
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.
Rebeccamycin and staurosporine represent two broad classes of indolocarbazole glycoside natural products with antitumor properties. Based upon previous sequence annotation and in vivo studies, rebG encodes for the rebeccamycin N-glucosyltransferase, and rebM for the requisite 4'-O-methyltransferas ... >> More
Rebeccamycin and staurosporine represent two broad classes of indolocarbazole glycoside natural products with antitumor properties. Based upon previous sequence annotation and in vivo studies, rebG encodes for the rebeccamycin N-glucosyltransferase, and rebM for the requisite 4'-O-methyltransferase. In the current study, an efficient in vivo biotransformation system for RebG was established in both Streptomyces lividans and Escherichia coli. Bioconversion experiments revealed RebG to glucosylate a set of indolocarbazole surrogates, the products of which could be further modified by in vitro RebM-catalyzed 4'-O-methylation. Both RebG and RebM displayed substrate promiscuity, and evidence for a remarkable lack of RebG regioselectivity in the presence of asymmetric substrates is also provided. In the context of the created indolocarbazole analogues, cytotoxicity assays also highlight the importance of 4'-O-methylation for their biological activity. << Less
ChemBioChem 7:795-804(2006) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.
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Cloning and expression of a gene encoding N-glycosyltransferase (ngt) from Saccarothrix aerocolonigenes ATCC39243.
Ohuchi T., Ikeda-Araki A., Watanabe-Sakamoto A., Kojiri K., Nagashima M., Okanishi M., Suda H.
In the course of our bioconversion studies on the derivatives of an indolocarbazole, J-104303, Saccharothrix aerocolonigenes ATCC39243 was found to convert J-104303, which was added into the culture medium, to its glycosylated derivative, J-109384. In order to clone the gene having the ability to ... >> More
In the course of our bioconversion studies on the derivatives of an indolocarbazole, J-104303, Saccharothrix aerocolonigenes ATCC39243 was found to convert J-104303, which was added into the culture medium, to its glycosylated derivative, J-109384. In order to clone the gene having the ability to convert J-104303 to J-109384, a library of Saccharothrix aerocolonigenes ATCC39243 DNA fragments was constructed using Streptomyces lividans TK21 and pIJ702 as host strain and vector, respectively. By examining more than 5,000 transformants, one was found to convert J-104303 to J-109384. Sequence analysis of the inserted DNA fragment revealed an open reading frame with 1,245 base pairs, named ngt. The transformant containing this ngt gene was also found to introduce a D-glucose moiety into 6-N-methylarcyriaflavin C. Furthermore, when ngt was introduced into Streptomyces mobaraensis BA13793, a producer of J-104303, the resulting transformant produced J-109384 directly. << Less