Enzymes
| UniProtKB help_outline | 1 proteins |
| Enzyme class help_outline |
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- Name help_outline 8-demethyltetracenomycin C Identifier CHEBI:31144 (CAS: 71135-22-3) help_outline Charge 0 Formula C22H18O11 InChIKeyhelp_outline DFURSAVCHZIKSU-STZQEDGTSA-N SMILEShelp_outline COC(=O)c1c(O)cc2cc3C(=O)[C@@]4(O)[C@H](O)C(OC)=CC(=O)[C@@]4(O)C(=O)c3c(O)c2c1C 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 dTDP-β-L-rhamnose Identifier CHEBI:57510 (Beilstein: 4078636) help_outline Charge -2 Formula C16H24N2O15P2 InChIKeyhelp_outline ZOSQFDVXNQFKBY-CGAXJHMRSA-L SMILEShelp_outline C[C@@H]1O[C@H](OP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H](C[C@@H]2O)n2cc(C)c(=O)[nH]c2=O)[C@H](O)[C@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 7 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 8-demethyl-8-α-L-rhamnosyl-tetracenomycin C Identifier CHEBI:78283 Charge 0 Formula C28H28O15 InChIKeyhelp_outline QIJXKOOPLDVFLW-DWENXZEQSA-N SMILEShelp_outline C=1C([C@]2(C(C=3C(=C4C(=C(C(=CC4=CC3C([C@]2([C@@H](C1OC)O)O)=O)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)O)O)O)C(=O)OC)C)O)=O)O)=O 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 dTDP Identifier CHEBI:58369 Charge -3 Formula C10H13N2O11P2 InChIKeyhelp_outline UJLXYODCHAELLY-XLPZGREQSA-K SMILEShelp_outline Cc1cn([C@H]2C[C@H](O)[C@@H](COP([O-])(=O)OP([O-])([O-])=O)O2)c(=O)[nH]c1=O 2D coordinates Mol file for the small molecule Search links Involved in 31 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,176 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:42848 | RHEA:42849 | RHEA:42850 | RHEA:42851 | |
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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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Identification of a sugar flexible glycosyltransferase from Streptomyces olivaceus, the producer of the antitumor polyketide elloramycin.
Blanco G., Patallo E.P., Brana A.F., Trefzer A., Bechthold A., Rohr J., Mendez C., Salas J.A.
<h4>Background</h4>Elloramycin is an anthracycline-like antitumor drug related to tetracenomycin C which is produced by Streptomyces olivaceus Tü2353. Structurally is a tetracyclic aromatic polyketide derived from the condensation of 10 acetate units. Its chromophoric aglycon is glycosylated with ... >> More
<h4>Background</h4>Elloramycin is an anthracycline-like antitumor drug related to tetracenomycin C which is produced by Streptomyces olivaceus Tü2353. Structurally is a tetracyclic aromatic polyketide derived from the condensation of 10 acetate units. Its chromophoric aglycon is glycosylated with a permethylated L-rhamnose moiety at the C-8 hydroxy group. Only limited information is available about the genes involved in the biosynthesis of elloramycin. From a library of chromosomal DNA from S. olivaceus, a cosmid (16F4) was isolated that contains part of the elloramycin gene cluster and when expressed in Streptomyces lividans resulted in the production of a non-glycosylated intermediate in elloramycin biosynthesis, 8-demethyl-tetracenomycin C (8-DMTC).<h4>Results</h4>The expression of cosmid 16F4 in several producers of glycosylated antibiotics has been shown to produce tetracenomycin derivatives containing different 6-deoxysugars. Different experimental approaches showed that the glycosyltransferase gene involved in these glycosylation events was located in 16F4. Using degenerated oligoprimers derived from conserved amino acid sequences in glycosyltransferases, the gene encoding this sugar flexible glycosyltransferase (elmGT) has been identified. After expression of elmGT in Streptomyces albus under the control of the erythromycin resistance promoter, ermEp, it was shown that elmG can transfer different monosaccharides (both L- and D-sugars) and a disaccharide to 8-DMTC. Formation of a diolivosyl derivative in the mithramycin producer Streptomyces argillaceus was found to require the cooperative action of two mithramycin glycosyltransferases (MtmGI and MtmGII) responsible for the formation of the diolivosyl disaccharide, which is then transferred by ElmGT to 8-DMTC.<h4>Conclusions</h4>The ElmGT glycosyltransferase from S. olivaceus Tü2353 can transfer different sugars into the aglycon 8-DMTC. In addition to its natural sugar substrate L-rhamnose, ElmGT can transfer several L- and D-sugars and also a diolivosyl disaccharide into the aglycon 8-DMTC. ElmGT is an example of sugar flexible glycosyltransferase and can represent an important tool for combinatorial biosynthesis. << Less